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Oils And FatsPart 1

ContentsArticles

Oil 1Triglyceride 4Cooking oil 10Vegetable oil 19Fat 27Animal fat 30Saturated fat 32Unsaturated fat 39Monounsaturated fat 41Polyunsaturated fat 43Trans fat 47Omega-6 fatty acid 67Omega-3 fatty acid 71Omega-9 fatty acid 85Fatty acid 86Essential fatty acid 93Interesterified fat 97Short-chain fatty acid 99Palmitoleic acid 100Myristoleic acid 102Oleic acid 103Sapienic acid 106Elaidic acid 108Vaccenic acid 110Linoelaidic acid 112Linoleic acid 113Arachidonic acid 119alpha-Linolenic acid 127Eicosapentaenoic acid 132Erucic acid 135Docosahexaenoic acid 140Caprylic acid 148Decanoic acid 150Lauric acid 153

Myristic acid 156Palmitic acid 158Stearic acid 161Arachidic acid 164Behenic acid 166Lignoceric acid 168Cerotic acid 170Melissic acid 171

ReferencesArticle Sources and Contributors 173Image Sources, Licenses and Contributors 178

Article LicensesLicense 180

Oil 1

OilAn oil is any neutral chemical substance that is a viscous liquid at ambient temperatures, is immiscible with waterbut soluble in alcohols or ethers. Oils have a high carbon and hydrogen content and are usually flammable andslippery (nonpolar). Oils may be animal, vegetable, or petrochemical in origin, volatile or non-volatile.[1]

EtymologyFirst attested in English 1176, the word oil comes from Old French "oile", from Latin "oleum",[2] which in turncomes from the Greek "ἔλαιον" (elaion), "olive oil, oil"[3] and that from "ἐλαία" (elaia), "olive tree".[4] The earliestattested form of the word is the Mycenaean Greek e-ra-wo, written in Linear B syllabic script.[5]

Types

Organic oilsOrganic oils are produced in remarkable diversity by plants, animals, and other organisms through natural metabolicprocesses. Lipid is the scientific term for the fatty acids, steroids and similar chemicals often found in the oilsproduced by living things, while oil refers to an overall mixture of chemicals. Organic oils may also containchemicals other than lipids, including proteins, waxes and alkaloids.Lipids can be classified by the way that they are made by an organism, their chemical structure and their limitedsolubility in water compared to oils. They have a high carbon and hydrogen content and are considerably lacking inoxygen compared to other organic compounds and minerals; they tend to be relatively nonpolar molecules, but mayinclude both polar and nonpolar regions as in the case of phospholipids and steroids.[6]

Mineral oilsCrude oil, or petroleum, and its refined components, collectively termed petrochemicals, are crucial resources in themodern economy. Crude oil originates from ancient fossilized organic materials, such as zooplankton and algae,which geochemical processes convert into oil.[7] It is classified as a mineral oil because it does not have an organicorigin on human timescales, but is instead obtained from rocks, underground traps, or sands. Mineral oil also refersto several specific distillates of crude oil.

Oil 2

Applications

A bottle of olive oilused in food

Cosmetics

Oils are applied to hair to give it a lustrous look, to prevent tangles and roughness and tostabilize the hair to promote growth.[8][9] See Hair conditioner.

Religion

Oils are commonly used in ritual anointments. As a particular example, holy anointing oil hasbeen an important ritual liquid for Judaism and Christianity.

Painting

Color pigments are easily suspended in oil, making it suitable as a supporting medium forpaints. The oldest known extant oil paintings date from 650 AD.[10]

Heat transfer

Oils are used as coolants in oil cooling, for instance in electric transformers. Oils are also usedto enhance heating in other applications, such as cooking (especially in frying).

LubricationOils are commonly used as lubricants. Mineral oils are more commonly used as machine lubricants than biologicaloils are. Whale oil is preferred for lubricating clocks, because it does not evaporate, leaving dust, although its usewas banned in 1980.[11] As no suitable substitute is available, whale oil is still used in space (in small quantities).[12]

FuelSome oils burn in liquid or aerosol form, generating light, and heat which can be used directly or converted intoother forms of energy such as electricity or mechanical work. To obtain many fuel oils, crude oil is pumped from theground and is shipped via oil tanker to an oil refinery. There, it is converted from crude oil to diesel fuel(petrodiesel), ethane (and other short-chain alkanes), fuel oils (heaviest of commercial fuels, used in ships/furnaces),gasoline (petrol), jet fuel, kerosene, benzene (historically), and liquefied petroleum gas. A 42 gallon barrel (U.S.) ofcrude oil produces approximately 10 gallons of diesel, 4 gallons of jet fuel, 19 gallons of gasoline, 7 gallons of otherproducts, 3 gallons split between heavy fuel oil and liquified petroleum gases,[13] and 2 gallons of heating oil. Thetotal production of a barrel of crude into various products results in an increase to 45 gallons.[13] Not all oils used asfuels are mineral oils, see biodiesel and vegetable oil fuel.In the 18th and 19th centuries, whale oil was commonly used for lamps, which was replaced with natural gas andthen electricity.[14]

Oil 3

Chemical feedstockCrude oil can be refined into a wide variety of component hydrocarbons. Petrochemicals are the refined componentsof crude oil and the chemical products made from them. They are used as detergents, fertilizers, medicines, paints,plastics, synthetic fibers, and synthetic rubber.Organic oils are another important chemical feedstock, especially in green chemistry.

References[1] "oil" (http:/ / oed. com/ search?searchType=dictionary& q=oil). Oxford English Dictionary (3rd ed.). Oxford University Press. 2001. .[2] oleum (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0059:entry=oleum), Charlton T. Lewis, Charles Short, A

Latin Dictionary, on Perseus Digital Library[3] ἔλαιον (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0057:entry=e)/ laion), Henry George Liddell, Robert Scott,

A Greek-English Lexicon, on Perseus Digital Library[4] ἐλαία (http:/ / www. perseus. tufts. edu/ hopper/ text?doc=Perseus:text:1999. 04. 0057:entry=e)lai/ a), Henry George Liddell, Robert Scott, A

Greek-English Lexicon, on Perseus Digital Library[5] Palaeolexicon (http:/ / www. palaeolexicon. com/ ), Word study tool of ancient languages[6] Alberts, Bruce; Johnson, Alexander; Lewis, Julian; Raff, Martin; Roberts, Keith; Walter, Peter. Molecular Biology of the Cell. New York:

Garland Science, 2002, pp. 62, 118-119.[7] Kvenvolden, Keith A. (2006). "Organic geochemistry – A retrospective of its first 70 years". Organic Geochemistry 37: 1.

doi:10.1016/j.orggeochem.2005.09.001.[8] Basil (Ocimum basilicum) (http:/ / www. montanaemuranch. com/ natural-ingredients-for-skin-care/ )[9] Best Oil for Hair Growth (http:/ / www. onlymyhealth. com/ best-oil-hair-growth-1323860232)[10] "Oldest Oil Paintings Found in Afghanistan" (http:/ / dsc. discovery. com/ news/ 2008/ 02/ 19/ oldest-oil-painting. html), Rosella Lorenzi,

Discovery News. Feb. 19, 2008.[11] Cuckoo Clock Questions (http:/ / www. frankenmuthclock. com/ questionscuckoo. htm)[12] Troubled waters: Did we really save the whale? (http:/ / www. independent. co. uk/ environment/ nature/

troubled-waters-did-we-really-save-the-whale-935193. html)[13] U.S. Energy Information Administration (EIA) (http:/ / www. eia. gov/ energyexplained/ index. cfm?page=oil_home) — Retrieved

2011-10-02.[14] Whale Oil (http:/ / www. petroleumhistory. org/ OilHistory/ pages/ Whale/ whale. html)

External links• Petroleum Online e-Learning resource from IHRDC (http:/ / www. petroleumonline. com)

Triglyceride 4

Triglyceride

Example of an unsaturated fat triglyceride. Leftpart: glycerol, right part from top to bottom:

palmitic acid, (contains)oleic acid, alpha-linolenicacid, chemical formula: C55H98O6

A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is anester derived from glycerol and three fatty acids.[1] There are manytriglycerides: depending on the oil source, some are highly unsaturated,some less so.

Saturated compounds are "saturated" with hydrogen — all availableplaces where hydrogen atoms could be bonded to carbon atoms areoccupied. Unsaturated compounds have double bonds (C=C) betweencarbon atoms, reducing the number of places where hydrogen atomscan bond to carbon atoms. Saturated compounds have single bonds(C-C) between the carbon atoms, and the other bond is bound tohydrogen atoms (for example =CH-CH=, -CH2-CH2-, etc.).

Unsaturated fats have a lower melting point and are more likely to be liquid. Saturated fats have a higher meltingpoint and are more likely to be solid at room temperature.

Triglycerides are the main constituents of vegetable oil (typically more unsaturated) and animal fats (typically moresaturated).[2] In humans, triglycerides are a mechanism for storing unused calories, and their high concentration inblood correlates with the consumption of starchy and other high carbohydrate foods . Triglycerides are a majorcomponent of human skin oils.[3]

Chemical structureTriglycerides are formed by combining glycerol with three molecules of fatty acid. Alcohols have a hydroxyl (HO-)group. Organic acids have a carboxyl (-COOH) group. Alcohols and organic acids join to form esters. The glycerolmolecule has three hydroxyl (HO-) groups. Each fatty acid has a carboxyl group (-COOH). In triglycerides, thehydroxyl groups of the glycerol join the carboxyl groups of the fatty acid to form ester bonds:

HOCH2CH(OH)CH2OH + RCO2H + R'CO2H + R''CO2H → RCO2CH2CH(O2CR')CO2R'' + 3H2OThe three fatty acids (RCO2H, R'CO2H, R''CO2H in the above equation) are usually different, but many kinds oftriglycerides are known. The chain lengths of the fatty acids in naturally occurring triglycerides vary, but mostcontain 16, 18, or 20 carbon atoms. Natural fatty acids found in plants and animals are typically composed of onlyeven numbers of carbon atoms, reflecting the pathway for their biosynthesis from the two-carbon building-blockacetyl CoA. Bacteria, however, possess the ability to synthesise odd- and branched-chain fatty acids. As a result,ruminant animal fat contains odd-numbered fatty acids, such as 15, due to the action of bacteria in the rumen. Manyfatty acids are unsaturated, some are polyunsaturated, e.g., those derived from linoleic acid.Most natural fats contain a complex mixture of individual triglycerides. Because of this, they melt over a broad rangeof temperatures. Cocoa butter is unusual in that it is composed of only a few triglycerides, derived from palmitic,oleic, and stearic acids.

Triglyceride 5

MetabolismThe enzyme pancreatic lipase acts at the ester bond, hydrolysing the bond and "releasing" the fatty acid. Intriglyceride form, lipids cannot be absorbed by the duodenum. Fatty acids, monoglycerides (one glycerol, one fattyacid), and some diglycerides are absorbed by the duodenum, once the triglycerides have been broken down.In the intestine, following the secretion of lipases and bile, triglycerides are split into monoacylglycerol and free fattyacids in a process called lipolysis, which are subsequently moved to absorptive enterocytes, cells lining theintestines. The triglycerides are rebuilt in the enterocytes from their fragments and packaged together withcholesterol and proteins to form chylomicrons. These are excreted from the cells and collected by the lymph systemand transported to the large vessels near the heart before being mixed into the blood. Various tissues can capture thechylomicrons, releasing the triglycerides to be used as a source of energy. Fat and liver cells can synthesize and storetriglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdownof the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids asan energy source (unless converted to a ketone), the glycerol component of triglycerides can be converted intoglucose, via glycolysis by conversion into Dihydroxyacetone phosphate and then into Glyceraldehyde 3-phosphate,for brain fuel when it is broken down. Fat cells may also be broken down for that reason, if the brain's needs everoutweigh the body's.Triglycerides cannot pass through cell membranes freely. Special enzymes on the walls of blood vessels calledlipoprotein lipases must break down triglycerides into free fatty acids and glycerol. Fatty acids can then be taken upby cells via the fatty acid transporter (FAT).Triglycerides, as major components of very-low-density lipoprotein (VLDL) and chylomicrons, play an importantrole in metabolism as energy sources and transporters of dietary fat. They contain more than twice as much energy(approximately 9 kcal/g or 38 kJ/g ) as carbohydrates (approximately 4 kcal/g or 17 kJ/g ).

Role in diseaseIn the human body, high levels of triglycerides in the bloodstream have been linked to atherosclerosis and, byextension, the risk of heart disease and stroke. However, the relative negative impact of raised levels of triglyceridescompared to that of LDL:HDL ratios is as yet unknown. The risk can be partly accounted for by a strong inverserelationship between triglyceride level and HDL-cholesterol level.

GuidelinesThe American Heart Association has set guidelines for triglyceride levels:[4]

Level mg/dL Level mmol/L Interpretation

<150 <1.70 Normal range, low risk

151-199 1.70-2.25 Slightly above normal

200-499 2.26-5.65 Some Risk

>500 >5.65 Very high: high risk

These levels are tested after fasting 8 to 12 hours. Triglyceride levels remain temporarily higher for a period of timeafter eating.

Triglyceride 6

Reducing triglyceride levelsDiets high in refined carbohydrates, with carbohydrates accounting for more than 60% of the total energy intake, canincrease triglyceride levels.[5] Of note is how the correlation is stronger for those with higher BMI (28+) and insulinresistance (more common among overweight and obese) is a primary suspect cause of this phenomenon ofcarbohydrate-induced hypertriglyceridemia.[6]

There is evidence that carbohydrate consumption causing a high glycemic index can cause insulin overproductionand increase triglyceride levels in women.[7]

Adverse changes associated with carbohydrate intake, including triglyceride levels, are stronger risk factors for heartdisease in women than in men.[8]

Triglyceride levels are also reduced by exercise and by consuming omega-3 fatty acids from fish, flax seed oil, andother sources. See health effects of Omega-3.Carnitine has the ability to lower blood triglyceride levels.[9] In some cases, fibrates have been used to bring downtriglycerides substantially.[10]

Heavy use of alcohol can elevate triglycerides levels.[11]

Industrial usesLinseed oil and related oils are important components of useful products used in oil paints and related coatings.Linseed oil is rich in di- and triunsaturated fatty acid components, which tend to harden in the presence of oxygen.The hardening process is peculiar to these so-called "drying oils". It is caused by a polymerization process thatbegins with oxygen molecules attacking the carbon backbone.Triglycerides are also split into their components via transesterification during the manufacture of biodiesel. Theresulting fatty acid esters can be used as fuel in diesel engines. The glycerin has many uses, such as in themanufacture of food and in the production of pharmaceuticals.

StainingStaining for fatty acids, triglycerides, lipoproteins, and other lipids is done through the use of lysochromes(fat-soluble dyes). These dyes can allow the qualification of a certain fat of interest by staining the material a specificcolor. Some examples: Sudan IV, Oil Red O, and Sudan Black B.

Interactive pathway mapClick on genes, proteins and metabolites below to link to respective articles. [12]

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Triglyceride 7

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Triglyceride 8

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Triglyceride 9

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Statin Pathway edit [13]

References[1] "Nomenclature of Lipids" (http:/ / www. chem. qmul. ac. uk/ iupac/ lipid/ ). IUPAC-IUB Commission on Biochemical Nomenclature (CBN).

. Retrieved 2007-03-08.[2][2] Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.[3] Lampe, M.A.; A.L. Burlingame, J. Whitney, M.L. Williams, B.E. Brown, E. Roitman, and M. Elias (1983). "Human stratum corneum lipids:

characterization and regional variations". J. Lipid Res. 24: 120 - 130.[4] "Triglycerides" (http:/ / www. heart. org/ HEARTORG/ GettingHealthy/ NutritionCenter/ Triglycerides_UCM_306029_Article. jsp).

Heart.org. . Retrieved 2012-09-12.[5] "AHA: What Cholesterol levels mean - Triglycerides tab" (http:/ / www. heart. org/ HEARTORG/ Conditions/ Cholesterol/

AboutCholesterol/ What-Your-Cholesterol-Levels-Mean_UCM_305562_Article. jsp). Heart.org. . Retrieved 2012-10-24.[6] Parks, E.J. (2002). "Dietary carbohydrate’s effects on lipogenesis and the relationship of lipogenesis to blood insulin and glucose

concentrations". British Journal of Nutrition 87: S247–S253. doi:10.1079/BJN/2002544. PMID 12088525. "Those with a body mass index(BMI) equal to or greater than 28 kg/m2 experienced a 30% increase in TAG concentration, while those whose BMI was less than 28,experienced no change...These data demonstrate that certain characteristics (e.g., BMI) can make some individuals more sensitive with respectto lipid and lipoprotein changes when dietary CHO is increased. Such characteristics that have been identified from previous work in this fieldand include BMI, insulin sensitivity (Coulston et al. 1989), concentration of TAG before the dietary change is made (Parks et al. 2001),hormone replacement therapy (Kasim-Karakas et al. 2000), and genetic factors (Dreon et al. 2000)."

[7] "Focusing on Fiber?" (http:/ / www. drweil. com/ drw/ u/ id/ QAA298788). Drweil.com. . Retrieved 2010-08-02.[8] "Dietary Glycemic Load and Index and Risk of Coronary Heart Disease in a Large Italian Cohort" (http:/ / archinte. ama-assn. org/ cgi/

content/ abstract/ 170/ 7/ 640). Archives of internal medicine. . Retrieved 2010-05-01.[9][9] Balch, Phyllis A. Prescription for nutritional healing. 4th ed. New York: Avery, 2006. p. 54 Carnitine[10] "Fibrates: Where Are We Now?: Fibrates and Triglycerides" (http:/ / www. medscape. com/ viewarticle/ 587134_7). Medscape.com. .

Retrieved 2010-08-02.[11] Hemat, R A S (2003). Principles of Orthomolecularism (http:/ / books. google. com/ ?id=ED_xI-CEzFYC& pg=PA254& lpg=PA254&

dq=alcohol+ consumption+ can+ elevate+ triglyceride+ levels). Urotext. p. 254. ISBN 1-903737-06-0. .[12] The interactive pathway map can be edited at WikiPathways: "Statin_Pathway_WP430" (http:/ / www. wikipathways. org/ index. php/

Pathway:WP430). .[13] http:/ / www. wikipathways. org/ index. php/ Pathway:WP430

Cooking oil 10

Cooking oil

Plant oils

Olive oil

Types

Vegetable oil (list)

Macerated oil (list)

Uses

Drying oil - Oil paint

Cooking oil

Fuel - Biodiesel

Components

Saturated fat

Monounsaturated fat

Polyunsaturated fat

Trans fat

Cooking oil is plant, animal or synthetic fat used in frying, baking and other types of cooking. It is also used in foodpreparation and flavoring that doesn't involve heat, such as salad dressings and bread dips, and in this sense might bemore accurately termed edible oil.Cooking oil is typically a liquid, although some oils that contain saturated fat, such as coconut oil, palm oil and palmkernel oil, are solid at room temperature.[1]

Types of cooking oil include: olive oil, palm oil, soybean oil, canola oil (rapeseed oil), pumpkin seed oil, corn oil,sunflower oil, safflower oil, peanut oil, grape seed oil, sesame oil, argan oil, rice bran oil and other vegetable oils.Oil can be flavoured with aromatic foodstuffs such as herbs, chillies or garlic.

Cooking oil 11

Health and nutrition

Olive oil

Italian olive oil

Sunflowerseed oil

The appropriate amount of fat as a component of daily food consumption is the topic of somecontroversy. Some fat is required in the diet, and fat (in the form of oil) is also essential inmany types of cooking. The FDA recommends that 30% or fewer of calories consumed dailyshould be from fat.[2] Other nutritionists recommend that no more than 10% of a person's dailycalories come from fat.[3] In extremely cold environments, a diet that is up to two-thirds fat isacceptable and can, in fact, be critical to survival.

While consumption of small amounts of saturated fats is essential, initial meta-analyses (1997,2003) found a high correlation between high consumption of such fats and coronary heartdisease.[4][5] Surprisingly, however, more recent meta-analyses (2009, 2010), based on cohortstudies and on controlled, randomized trials, find a positive[6] or neutral[7] effect from shiftingconsumption from carbohydrate to saturated fats as a source of calories, and only a modestadvantage for shifting from saturated to polyunsaturated fats (10% lower risk for 5%replacement).[7]

Mayo Clinic has highlighted oils that are high in saturated fats, including coconut, palm oiland palm kernel oil. Those of lower amounts of saturated fats, and higher levels of unsaturated(preferably monounsaturated) fats like olive oil, peanut oil, canola oil, avocado, safflower,corn, sunflower, soy, mustard and cottonseed oils are generally healthier.[8] The NationalHeart, Lung and Blood Institute[9] and World Heart Federation[10] have urged saturated fats bereplaced with polyunsaturated and monounsaturated fats. The health body lists olive andcanola oils as sources of monounsaturated oils while soybean and sunflower oils are rich withpolyunsaturated fat. Results of research carried out in Costa Rica in 2005 suggest thatconsumption of non-hydrogenated unsaturated oils like soybean and sunflower are preferableto the consumption of palm oil.[11]

Not all saturated fats have negative effects on cholesterol.[12] Some studies indicate thatPalmitic acid in palm oil does not behave like other saturated fats, and is neutral on cholesterollevels because it is equally distributed among the three "arms" of the triglyceride molecule.[13]

Further, it has been reported that palm oil consumption reduces blood cholesterol incomparison with other traditional sources of saturated fats such as coconut oil, dairy andanimal fats.[14]

Saturated fat is required by the body and brain to function properly. In fact, one study in Brazilcompared the effects of soybean oil to coconut oil (a highly saturated fat) and found that whileboth groups showed a drop in BMI, the soybean oil group showed an increase in overallcholesterol (including a drop in HDL, the good cholesterol). The coconut oil group actuallyshowed an increase in the HDL:LDL ratio (meaning there was more of the good cholesterol),as well as smaller waist sizes (something that was not shown in the soybean oil group.[15]

In 2007, scientists Kenneth C. Hayes and Pramod Khosla of Brandeis University and WayneState University indicated that the focus of current research has shifted from saturated fats toindividual fats and percentage of fatty acids (saturates, monounsaturates, polyunsaturates) in the diet. An adequateintake of both polyunsaturated and saturated fats is needed for the ideal LDL/HDL ratio in blood, as both contributeto the regulatory balance in lipoprotein metabolism.[16]

Oils high in unsaturated fats may help to lower "bad" LDL cholesterol and may also raise "good" HDL cholesterol,though these effects are still under study.

Cooking oil 12

Peanut, cashew, and other nut-based oils may also present a hazard to persons with a nut allergy. A severe allergicreaction may cause anaphylactic shock and result in death.

Trans fatsUnlike other dietary fats, trans fats are not essential, and they do not promote good health.[17] The consumption oftrans fats increases one's risk of coronary heart disease[18] by raising levels of "bad" LDL cholesterol and loweringlevels of "good" HDL cholesterol.[19] Trans fats from partially hydrogenated oils are more harmful than naturallyoccurring oils.[20]

Several large studies[21][22][23][24] indicate a link between consumption of high amounts of trans fat and coronaryheart disease and possibly some other diseases. The United States Food and Drug Administration (FDA), theNational Heart, Lung and Blood Institute and the American Heart Association (AHA) all have recommendedlimiting the intake of trans fats.

Cooking with oilHeating an oil changes its characteristics. Oils that are healthy at room temperature can become unhealthy whenheated above certain temperatures. When choosing a cooking oil, it is important to match the oil's heat tolerance withthe cooking method.[25]

A 2001 parallel review of 20-year dietary fat studies in the United Kingdom, the United States of America, andSpain[26] found that polyunsaturated oils like soya, canola, sunflower, and corn oil degrade easily to toxiccompounds when heated. Prolonged consumption of burnt oils led to atherosclerosis, inflammatory joint disease, anddevelopment of birth defects. The scientists also questioned global health authorities' recommendation that largeamounts of polyunsaturated fats be incorporated into the human diet without accompanying measures to ensure theprotection of these fatty acids against heat- and oxidative-degradation.Palm oil contains more saturated fats than canola oil, corn oil, linseed oil, soybean oil, safflower oil, and sunfloweroil. Therefore, palm oil can withstand the high heat of deep frying and is resistant to oxidation compared to highlyunsaturated vegetable oils.[27] Since about 1900, palm oil has been increasingly incorporated into food by the globalcommercial food industry because it remains stable in deep frying or in baking at very high temperatures[28][29] andfor its high levels of natural antioxidants.[30]

Oils that are suitable for high-temperature frying (above 230 °C/446 °F) because of their high smoke point•• Avocado oil•• Corn oil•• Mustard oil•• Palm oil• Peanut oil (marketed as "groundnut oil" in the UK and India)•• Rice bran oil•• Safflower oil•• Semirefined Sesame oil•• Soybean oil• Semirefined Sunflower Oil [31]

Cooking oil 13

Storing and keeping oilWhether refined or not, all oils are sensitive to heat, light, and exposure to oxygen. Rancid oil has an unpleasantaroma and acrid taste, and its nutrient value is greatly diminished. To delay the development of rancid oil, a blanketof an inert gas, usually nitrogen, is applied to the vapor space in the storage container immediately after production.This is referred to as tank blanketing. Vitamin E oil is a natural antioxidant that can also be added to cooking oils toprevent rancidification.All oils should be kept in a cool, dry place. Oils may thicken, but they will soon return to liquid if they stand at roomtemperature. To prevent negative effects of heat and light, oils should be removed from cold storage just longenough for use. Refined oils high in monounsaturated fats keep up to a year (olive oil will keep up to a few years),while those high in polyunsaturated fats keep about six months. Extra-virgin and virgin olive oils keep at least 9months after opening. Other monounsaturated oils keep well up to eight months, while unrefined polyunsaturatedoils will keep only about half as long.In contrast, saturated oils, such as coconut oil and palm oil, have much longer shelf lives and can be safely stored atroom temperature.[32] Their lack of polyunsaturated content causes them to be more stable.[33]

Types of oils and their characteristicsLighter, more refined oils tend to have higher smoke points. Experience using an oil is generally a sufficientlyreliable guide. Although outcomes of empirical tests are sensitive to the qualities of particular samples (brand,composition, refinement, process), the data below should be helpful in comparing the properties of different oils.Smoking oil indicates a risk of combustion, and left unchecked can also set off a fire alarm. When using any cookingoil, should it begin to smoke, heat should be reduced immediately. Generally, one should be fully prepared toextinguish a burning oil fire before heating, typically by having on hand the lid to place on the pan, or (for the worstcase) having on hand the proper fire extinguisher.

Type of oil or fat Saturated Monounsaturated Polyunsaturated Smoke point[34]

Uses

Almond 8% 66% 26% 221 °C (430 °F) Baking, sauces, flavoring

Avocado 12% 74% 14% 271 °C (520 °F) Frying, sautéing, dipping oil, salad oil

Butter 66% 30% 4% 150 °C (302 °F) Cooking, baking, condiment, sauces, flavoring

Ghee, clarified butter 65% 32% 3% 190–250 °C(374–482 °F)

Deep frying, cooking, sautéeing, condiment,flavoring

Canola oil 6% 62% 32% 204 °C (399 °F) Frying, baking, salad dressings

Coconut oil 92% 6% 2% 177 °C (351 °F) Commercial baked goods, candy and sweets,whipped toppings, nondairy coffee creamers,shortening

Rice bran oil 20% 47% 33% 254 °C (489 °F) Cooking, frying, deep frying, salads, dressings.Very clean flavoured & palatable.

Corn oil 13% 25% 62% 236 °C (457 °F) Frying, baking, salad dressings, margarine,shortening

Cottonseed oil 24% 26% 50% 216 °C (421 °F) Margarine, shortening, salad dressings,commercially fried products

Grape seed oil 12% 17% 71% 204 °C (399 °F) Cooking, salad dressings, margarine

Hemp oil 9% 12% 79% 165 °C (329 °F) Cooking, salad dressings, ...

Lard 41% 47% 2% 138–201 °C(280–394 °F)

Baking, frying

Cooking oil 14

Margarine, hard 80% 14% 6% 150 °C(302 °F)[35]

Cooking, baking, condiment

Mustard oil 13% 60% 21% 254 °C (489 °F) Cooking, frying, deep frying, salads, dressings.Very clean flavoured & palatable.

Margarine, soft 20% 47% 33% 150–160 °C(302–320 °F)

Cooking, baking, condiment

Macadamia oil 12.5% 84% 3.5% 210 °C (410 °F) Cooking, frying, deep frying, salads, dressings. Aslightly nutty odour.

Diacylglycerol(DAG) oil

3.5% 37.95% 59% 215 °C (419 °F) Frying, baking, salad oil

Olive oil (extravirgin)

14% 73% 11% 190 °C (374 °F) Cooking, salad oils, margarine

Olive oil (virgin) 14% 73% 11% 215 °C (419 °F) Cooking, salad oils, margarine

Olive oil (refined) 14% 73% 11% 225 °C (437 °F) Sautee, stir frying, deep frying, cooking, salad oils,margarine

Olive oil (extra light) 14% 73% 11% 242 °C (468 °F) Sautee, stir frying, frying, deep frying, cooking,salad oils, margarine

Palm oil 52% 38% 10% 230 °C (446 °F) Cooking, flavoring, vegetable oil, shortening

Peanut oil /groundnut oil

18% 49% 33% 231 °C (448 °F) Frying, cooking, salad oils, margarine

Pumpkin seed oil 8% 36% 57% 121 °C (250 °F) salad oils

Safflower oil 10% 13% 77% 265 °C (509 °F) Cooking, salad dressings, margarine

Sesame oil(Unrefined)

14% 43% 43% 177 °C (351 °F) Cooking

Sesame oil(semi-refined)

14% 43% 43% 232 °C (450 °F) Cooking, deep frying

Soybean oil 15% 24% 61% 241 °C (466 °F) Cooking, salad dressings, vegetable oil, margarine,shortening

Sunflower oil(linoleic)

11% 20% 69% 246 °C (475 °F) Cooking, salad dressings, margarine, shortening

Sunflower oil (higholeic)[36]

9% 82% 9% 160 °C (320 °F) Cooking

Tea seed oil[37] 22% 60% 18% 252 °C (486 °F) Cooking, salad dressings, stir frying, frying,margarine

Walnut(Semi-refined)

9% 23% 63% 204 °C(399 °F)[38]

Salad dressings, added to cold dishes to enhanceflavor

Cooking oil 15

Cooking oil extraction and refinementCooking oil extraction and refinement are separate processes. Extraction first removes the oil, typically from a seed,nut or fruit. Refinement then alters the appearance, texture, taste, smell, or stability of the oil to meet buyerexpectations.

ExtractionThere are three broad types of oil extraction:• Chemical solvent extraction, most commonly using hexane.• Pressing, using an expeller press or cold press (pressing at low temperatures to prevent oil heating).•• Decanter centrifuge.In large-scale industrial oil extraction you will often see some combination of pressing, chemical extraction and/orcentrifuging in order to extract the maximum amount of oil possible.[39] Cooking oil producers targeting the healthfood market often use cold press extraction only, as it provides an extraction process free of chemical solvents andhigh temperatures.

RefinementCooking oil can either be unrefined, or refined using one or more of the following refinement processes (in anycombination):•• Distilling, which heats the oil to evaporate off chemical solvents from the extraction process.•• Degumming, by passing hot water through the oil to precipitate out gums and proteins that are soluble in oil but

not in water, then discarding the water along with the impurities.•• Neutralization, or deacidification, which treats the oil with sodium hydroxide or sodium carbonate to pull out free

fatty acids, phospholipids, pigments, and waxes.• Bleaching, which removes "off-colored" components by treatment with fuller's earth, activated carbon, or

activated clays, followed by heating, filtering, then drying to recoup the oil.•• Dewaxing, or winterizing, improves clarity of oils intended for refrigeration by dropping them to low

temperatures and removing any solids that form.•• Deodorizing, by treating with high-heat pressurized steam to evaporate less stable compounds that might cause

"unusual" odors or tastes.• Preservative addition, such as BHA and BHT to help preserve oils that have been made less stable due to

high-temperature processing.Filtering, a non-chemical process which screens out larger particles, could be considered a step in refinement,although it doesn't alter the state of the oil. Most large-scale commercial cooking oil refinement will involve all ofthese steps in order to achieve a product that's uniform in taste, smell and appearance, and has a longer shelf life.[40]

Cooking oil intended for the health food market will often be unrefined, which can result in a less stable product butminimizes exposure to high temperatures and chemical processing.

Cooking oil 16

Waste cooking oil

A bin for spent cooking oil in Austin,Texas, USA, managed by a recycling

company.

Proper disposal of used cooking oil is an important waste-managementconcern. Oil is lighter than water and tends to spread into thin and broadmembranes which hinder the oxygenation of water. Because of this, a singlelitre of oil can contaminate as much as 1 million litres of water. Also, oil cancongeal on pipes provoking blockages.[41]

Because of this, cooking oil should never be dumped in the kitchen sink or inthe toilet bowl. The proper way to dispose of oil is to put it in a sealednon-recyclable container and discard it with regular garbage.[42] Placing thecontainer of oil in the refrigerator to harden also makes disposal easier andless messy.

Cooking oil can be recycled. It can be used to produce soap and biodiesel.[43]

Notes[1] "Dietary fats explained" (http:/ / www. nlm. nih. gov/ medlineplus/ ency/ patientinstructions/ 000104. htm). . Retrieved May 4, 2012.[2] "The Food Pyramid" (http:/ / web. archive. org/ web/ 20060822160207/ http:/ / www. cfsan. fda. gov/ ~dms/ fdpyrmid. html). FDA

Consumer. Archived from [http://www.cfsan.fda.gov/~dms/fdpyrmid.html the original] on 2006-08-22. . Retrieved 2006-09-18.[3] Dean Ornish, MD, Lifestyle Program (http:/ / www. webmd. com/ content/ pages/ 9/ 3068_9408. htm)[4] Clarke, R; Frost, C; Collins, R; Appleby, P; Peto, R (1997). "Dietary lipids and blood cholesterol: quantitative meta-analysis of metabolic

ward studies". BMJ 314 (7074): 112–7. PMC 2125600. PMID 9006469.[5] Mensink, RP; Zock, PL; Kester, AD; Katan, MB (2003). "Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL

cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials". The American journal of clinical nutrition 77 (5):1146–55. PMID 12716665.

[6] Jakobsen, M. U; O'Reilly, E. J; Heitmann, B. L; Pereira, M. A; Balter, K.; Fraser, G. E; Goldbourt, U.; Hallmans, G. et al. (2009). "Majortypes of dietary fat and risk of coronary heart disease: a pooled analysis of 11 cohort studies". American Journal of Clinical Nutrition 89 (5):1425–32. doi:10.3945/ajcn.2008.27124. PMC 2676998. PMID 19211817.

[7] Katan, Martijn B.; Mozaffarian, Dariush; Micha, Renata; Wallace, Sarah (2010). Katan, Martijn B.. ed. "Effects on Coronary Heart Diseaseof Increasing Polyunsaturated Fat in Place of Saturated Fat: A Systematic Review and Meta-Analysis of Randomized Controlled Trials". PLoSMedicine 7 (3): e1000252. doi:10.1371/journal.pmed.1000252. PMC 2843598. PMID 20351774.

[8] Dietary fats: Know which types to choose (http:/ / www. mayoclinic. com/ health/ fat/ NU00262) Mayo Clinic website[9] Choose foods low in saturated fat (http:/ / www. nhlbi. nih. gov/ chd/ Tipsheets/ satfat. htm) National Heart, Lung, and Blood Institute

(NHLBI), NIH Publication No. 97-4064. 1997.[10] Diet & cardiovascular disease (http:/ / www. world-heart-federation. org/ press/ facts-figures/ diet-and-cvd/ ) World Heart Federation

website[11] Kabagambe, Baylin, Ascherio & Campos, EK; Baylin, A; Ascherio, A; Campos, H (November 2005). "The Type of Oil Used for Cooking Is

Associated with the Risk of Nonfatal Acute Myocardial Infarction in Costa Rica" (http:/ / jn. nutrition. org/ cgi/ content/ abstract/ 135/ 11/2674). Journal of Nutrition 135 (11): 2674–2679. PMID 16251629. .

[12] Ng, TK; Hassan, K; Lim, JB; Lye, MS; Ishak, R (1991). "Nonhypercholesterolemic effects of a palm-oil diet in Malaysian volunteers"(http:/ / www. ajcn. org/ cgi/ content/ abstract/ 53/ 4/ 1015S). American Journal of Clinical Nutrition 53 (4): 1015S–1020S. PMID 2012009. .

[13] A critical review of the cholesterolemic effects of palm oil (http:/ / www. unu. edu/ Unupress/ food/ 8F152e/ 8F152E02. htm) Tony NgKock Wai, The United Nations University Press, Food and Nutrition Bulletin, Volume 15 (1993/1994), Number 2, June 1994

[14] Chong, YH; Ng, TK (1991). "Effects of palm oil on cardiovascular risk". The Medical journal of Malaysia 46 (1): 41–50. PMID 1836037.[15] Assun��o, Monica L.; Ferreira, Haroldo S.; Dos Santos, Aldenir F.; Cabral, Cyro R.; Flor�ncio, Telma M. M. T. (2009). "Effects of

Dietary Coconut Oil on the Biochemical and Anthropometric Profiles of Women Presenting Abdominal Obesity". Lipids 44 (7): 593–601.doi:10.1007/s11745-009-3306-6. PMID 19437058.

[16] Hayes, Kenneth; Khosla, Pramod (2007). "The complex interplay of palm oil fatty acids on blood lipids". European Journal of Lipid Scienceand Technology 109 (4): 453. doi:10.1002/ejlt.200700005.

[17] Food and nutrition board, institute of medicine of the national academies (2005). Dietary Reference Intakes for Energy, Carbohydrate,Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients) (http:/ / www. nap. edu/ openbook/ 0309085373/ html/ 423.html). National Academies Press. p. 423. ISBN 0-309-08537-3. .

[18] Food and nutrition board, institute of medicine of the national academies (2005). Dietary Reference Intakes for Energy, Carbohydrate,Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids (Macronutrients) (http:/ / darwin. nap. edu/ books/ 0309085373/ html/ 504.html). National Academies Press. p. 504. ISBN 0-309-08537-3. .

Cooking oil 17

[19] "Trans fat: Avoid this cholesterol double whammy" (http:/ / www. mayoclinic. com/ health/ trans-fat/ CL00032). Mayo Foundation forMedical Education and Research (MFMER).. . Retrieved 2007-12-10.

[20] Mozaffarian, Dariush; Katan, Martijn B.; Ascherio, Alberto; Stampfer, Meir J.; Willett, Walter C. (2006). "Trans Fatty Acids andCardiovascular Disease". New England Journal of Medicine 354 (15): 1601–113. doi:10.1056/NEJMra054035. PMID 16611951.

[21] Willett, WC; Stampfer, MJ; Manson, JE; Colditz, GA; Speizer, FE; Rosner, BA; Sampson, LA; Hennekens, CH (1993). "Intake of transfatty acids and risk of coronary heart disease among women". Lancet 341 (8845): 581–5. doi:10.1016/0140-6736(93)90350-P.PMID 8094827.

[22] Hu, Frank B.; Stampfer, Meir J.; Manson, Joann E.; Rimm, Eric; Colditz, Graham A.; Rosner, Bernard A.; Hennekens, Charles H.; Willett,Walter C. (1997). "Dietary Fat Intake and the Risk of Coronary Heart Disease in Women". New England Journal of Medicine 337 (21):1491–9. doi:10.1056/NEJM199711203372102. PMID 9366580.

[23] Hayakawa, Kyoko; Linko, Yu-Yen; Linko, Pekka (2000). "The role of trans fatty acids in human nutrition". Starch - Stärke 52 (6–7):229–35. doi:10.1002/1521-379X(200007)52:6/7<229::AID-STAR229>3.0.CO;2-G.

[24] The Nurses' Health Study (NHS) (http:/ / www. channing. harvard. edu/ nhs/ )[25] Orna Izakson. "Oil right: choose wisely for heart-healthy cooking - Eating Right" (http:/ / findarticles. com/ p/ articles/ mi_m1594/ is_2_14/

ai_98469943/ pg_2). E: the Environmental Magazine. .[26] Grootveld, Martin; Silwood, Christopher J.L.; Addis, Paul; Claxson, Andrew; Serra, Bartolome Bonet; Viana, Marta (2001). "Health effects

of oxidized heated oils". Foodservice Research International 13: 41–55. doi:10.1111/j.1745-4506.2001.tb00028.x.[27] De Marco, Elena; Savarese, Maria; Parisini, Cristina; Battimo, Ilaria; Falco, Salvatore; Sacchi, Raffaele (2007). "Frying performance of a

sunflower/palm oil blend in comparison with pure palm oil". European Journal of Lipid Science and Technology 109 (3): 237.doi:10.1002/ejlt.200600192.

[28] Che Man, YB; Liu, J.L.; Jamilah, B.; Rahman, R. Abdul (1999). "Quality changes of RBD palm olein, soybean oil and their blends duringdeep-fat frying". Journal of Food Lipids 6 (3): 181–193. doi:10.1111/j.1745-4522.1999.tb00142.x.

[29] Matthäus, Bertrand (2007). "Use of palm oil for frying in comparison with other high-stability oils". European Journal of Lipid Science andTechnology 109 (4): 400. doi:10.1002/ejlt.200600294.

[30] Sundram, K; Sambanthamurthi, R; Tan, YA (2003). "Palm fruit chemistry and nutrition" (http:/ / apjcn. nhri. org. tw/ server/ APJCN/volume12/ vol12. 3/ fullArticles/ Sundram. pdf). Asia Pacific journal of clinical nutrition 12 (3): 355–62. PMID 14506001. .

[31] "Smoke Points of Various Fats - Kitchen Notes - Cooking For Engineers" (http:/ / www. cookingforengineers. com/ article/ 50/Smoke-Points-of-Various-Fats). cookingforengineers.com. 2012 [last update]. . Retrieved July 3, 2012.

[32] Coconutoil.com (http:/ / www. coconutoil. com/ ray_peat_coconutoil. htm)[33] Articledashboard.com (http:/ / www. articledashboard. com/ Article/ Long-term-Cooking-Oil-Storage/ 900575)[34] The smoke point of oils depends primarily on their free fatty acid content (FFA) and molecular weight. Through repeated use, as in a deep

fryer, food residues or by-products of the cooking process will accumulate within the oil and lower its smoke point. The values shown in thetable must therefore be taken as approximate, and are not suitable for accurate or scientific use.F. D. Gunstone; D. Rousseau (2004). Rapeseedand canola oil: production, processing, properties and uses (http:/ / books. google. com/ books?id=gDuHzSsaWLYC&pg=PA91#v=onepage& q& f=false). Oxford: Blackwell Publishing Ltd. p. 91. ISBN 0-8493-2364-9. . Retrieved 2011-01-17.Brown, Amy L.(2010). Understanding Food: Principles and Preparation (http:/ / books. google. com/ books?id=ppMzyDFyHUwC&pg=PA468#v=onepage& q& f=false). Belmont, CA: Wadsworth Publishing. p. 468. ISBN 0-538-73498-1. . Retrieved 2011-01-16.

[35][35] The smoke point of margarine varies depending on the types of oils used in its formulation, but can be generally assumed to be similar tothat of butter.

[36] Sunflowernsa.com (http:/ / www. sunflowernsa. com/ oil/ default. asp?contentID=145)[37] "Triglyceride composition of tea seed oil" (http:/ / onlinelibrary. wiley. com/ doi/ 10. 1002/ jsfa. 2740271206/ abstract). . Retrieved March

24, 2012.[38] "Cooking Oil Smoke Points" (http:/ / www. goodeatsfanpage. com/ collectedinfo/ oilsmokepoints. htm). . Retrieved January 3, 2011.[39] "How cooking oil is made" (http:/ / www. madehow. com/ Volume-1/ Cooking-Oil. html). . Retrieved May 18, 2012.[40] "How cooking oil is made" (http:/ / www. madehow. com/ Volume-1/ Cooking-Oil. html). . Retrieved May 18, 2012.[41] "Tips to avoid water waste and to require the preservation of hydro-resources" (http:/ / www. natureba. com. br/ nature/ saving-water. htm).

Natureba - Educação Ambiental. . Retrieved 2007-09-05.[42] "Grease Disposal Tips to Help the City's Environment" (http:/ / nyc. gov/ html/ dep/ html/ residents/ congrease. shtml). NYC Department of

Environmental Protection. . Retrieved 2007-08-05.[43] "Production of biodiesel based on waste oils and/or waste fats from biogenic origin for use as fuel" (http:/ / www. mct. gov. br/ upd_blob/

0016/ 16059. pdf) (PDF). CDM - Executive Board. . Retrieved 2007-09-05.

Cooking oil 18

References• O'Brien, R.D. (1998). Fats and Oils: Formulating and Processing for Applications. Lancaster, PA: Technomic

Publishing Co., Inc.. ISBN 0-8493-1599-9.• Potter, N.N. and J.H. Hotchkiss (1995). Food Science (Fifth ed.). New York: Chapman & Hall. pp. 359–80,

402–7. ISBN 0-442-01398-1.

Further reading• Warner, K. (1999). "Impact of high-temperature food processing on fats and oils". Advances in experimental

medicine and biology 459: 67–77. PMID 10335369.• Fox, R. (2001). Frying oils (http:/ / books. google. com/ books?id=utrZlCcmb3cC& pg=PA195&

dq=#v=onepage& q& f=false). In Kaarin Goodburn (Ed.) EU Food Law. Woodhead. pp. 195–224. ISBN978-1-85573-557-6.

External links• American Oil Chemical Society (http:/ / www. aocs. org) official website• Food Oil Smoke Points (http:/ / www. canola-council. org/ food_oil_smoke. aspx) from the Canola Council• Review of Nutritional Attributes of Cold Pressed Hemp Seed Oil (http:/ / www. goodwebsite. co. uk/ kingsreport.

pdf) from King's College London• Algae: Another way to grow edible oils (http:/ / news. cnet. com/ Algae-Another-way-to-grow-edible-oils/

2100-11395_3-6227572. html)

Vegetable oil 19

Vegetable oil

Plant oils

Olive oil

Types

Vegetable oil (list)

Macerated oil (list)

Uses

Drying oil - Oil paint

Cooking oil

Fuel - Biodiesel

Components

Saturated fat

Monounsaturated fat

Polyunsaturated fat

Trans fat

A vegetable oil is a triglyceride extracted from a plant. Such oils have been part of human culture for millennia.[1]

The term "vegetable oil" can be narrowly defined as referring only to substances that are liquid at roomtemperature,[2] or broadly defined without regard to a substance's state of matter at a given temperature.[3] For thisreason, vegetable oils that are solid at room temperature are sometimes called vegetable fats. Vegetable oils arecomposed of triglycerides, as contrasted with waxes which lack glycerin in their structure. Although many plantparts may yield oil,[4] in commercial practice, oil is extracted primarily from seeds.

Vegetable oil 20

Uses of triglyceride vegetable oilOils extracted from plants have been used since ancient times and in many cultures. As an example, in a4,000-year-old "kitchen" unearthed in Indiana's Charlestown State Park, archaeologist Bob McCullough of IndianaUniversity-Purdue University Fort Wayne found evidence that natives used large slabs of rock to crush hickory nuts,then boiled them in water to extract the oil.[5]

Culinary usesMany vegetable oils are consumed directly, or indirectly as ingredients in food – a role that they share with someanimal fats, including butter and ghee. The oils serve a number of purposes in this role:• Shortening – to give pastry a crumbly texture.• Texture – oils can serve to make other ingredients stick together less.• Flavor – while less-flavorful oils command premium prices, some oils, such as olive, sesame, or almond oil, may

be chosen specifically for the flavor they impart.• Flavor base – oils can also "carry" flavors of other ingredients, since many flavors are present in chemicals that

are soluble in oil.Secondly, oils can be heated and used to cook other foods. Oils suitable for this objective must have a high flashpoint. Such oils include the major cooking oils – soybean, canola, sunflower, safflower, peanut, cottonseed, etc.Tropical oils, such as coconut, palm, and rice bran oils, are particularly valued in Asian cultures for high temperaturecooking, because of their unusually high flash point.

Hydrogenated oilsUnsaturated vegetable oils can be transformed through partial or complete "hydrogenation" into oils of highermelting point. The hydrogenation process involves "sparging" the oil at high temperature and pressure with hydrogenin the presence of a catalyst, typically a powdered nickel compound. As each carbon-carbon double-bond ischemically reduced to a single bond, two hydrogen atoms each form single bonds with the two carbon atoms. Theelimination of double bonds by adding hydrogen atoms is called saturation; as the degree of saturation increases, theoil progresses toward being fully hydrogenated. An oil may be hydrogenated to increase resistance to rancidity(oxidation) or to change its physical characteristics. As the degree of saturation increases, the oil's viscosity andmelting point increase.The use of hydrogenated oils in foods has never been completely satisfactory. Because the center arm of thetriglyceride is shielded somewhat by the end fatty acids, most of the hydrogenation occurs on the end fatty acids,thus making the resulting fat more brittle. A margarine made from naturally more saturated oils will be more plastic(more "spreadable") than a margarine made from hydrogenated soy oil. While full hydrogenation produces largelysaturated fatty acids, partial hydrogenation results in the transformation of unsaturated cis fatty acids to trans fattyacids in the oil mixture due to the heat used in hydrogenation. Since the 1970s, partially hydrogenated oils and theirtrans fats have increasingly been viewed as unhealthy.In the U.S., the Standard of Identity for a product labeled as "vegetable oil margarine" specifies only canola,safflower, sunflower, corn, soybean, or peanut oil may be used.[6] Products not labeled "vegetable oil margarine" donot have that restriction.

Vegetable oil 21

Industrial usesVegetable oils are used as an ingredient or component in many manufactured products.Many vegetable oils are used to make soaps, skin products, candles, perfumes and other personal care and cosmeticproducts. Some oils are particularly suitable as drying oils, and are used in making paints and other wood treatmentproducts. Dammar oil (a mixture of linseed oil and dammar resin), for example, is used almost exclusively in treatingthe hulls of wooden boats. Vegetable oils are increasingly being used in the electrical industry as insulators asvegetable oils are not toxic to the environment, biodegradable if spilled and have high flash and fire points.However, vegetable oils are less stable chemically, so they are generally used in systems where they are not exposedto oxygen, and they are more expensive than crude oil distillate. Synthetic tetraesters, which are similar to vegetableoils but with four fatty acid chains compared to the normal three found in a natural ester, are manufactured byFischer esterification. Tetraesters generally have high stability to oxidation and have found use as engine lubricants.Vegetable oil is being used to produce biodegradable hydraulic fluid[7] and lubricant.[8]

One limiting factor in industrial uses of vegetable oils is that all such oils eventually chemically decompose, turningrancid. Oils that are more stable, such as ben oil or mineral oil, are preferred for some industrial uses.Vegetable-based oils, like castor oil, have been used as medicine and as lubricants for a long time. Castor oil hasnumerous industrial uses, primarily due to the presence of hydroxyl groups on the fatty acid chains. Castor oil, andother vegetable oils which have been chemically modified to contain hydroxyl groups, are becoming increasinglyimportant in the production of polyurethane plastic for many applications. These modified vegetable oils are knownas natural oil polyols.

Pet food additiveVegetable oil is used in production of some pet foods. AAFCO defines vegetable oil, in this context, as the productof vegetable origin obtained by extracting the oil from seeds or fruits which are processed for edible purposes. Insome poorer grade pet foods, the oil is listed only as "vegetable oil", without specifying the particular oil.[9]

FuelVegetable oils are also used to make biodiesel, which can be used like conventional diesel. Some vegetable oilblends are used in unmodified vehicles but straight vegetable oil, also known as pure plant oil, needs speciallyprepared vehicles which have a method of heating the oil to reduce its viscosity. The vegetable oil economy isgrowing and the availability of biodiesel around the world is increasing.The NNFCC estimate that the total net greenhouse gas savings when using vegetable oils in place of fossilfuel-based alternatives for fuel production, range from 18 to 100%.[10]

ProductionTo produce vegetable oils, the oil first needs to be removed from the oil-bearing plant components, typically seeds.This can be done via mechanical or chemical extraction. The extracted oil can then be purified and, if required,refined or chemically altered.

Mechanical extractionOils can also be removed via mechanical extraction, termed "crushing" or "pressing." This method is typically used to produce the more traditional oils (e.g., olive, coconut etc.), and it is preferred by most "health-food" customers in the United States and in Europe. There are several different types of mechanical extraction.[11] Expeller-pressing extraction is common, though the screw press, ram press, and Ghani (powered mortar and pestle) are also used. Oil seed presses are commonly used in developing countries, among people for whom other extraction methods would be prohibitively expensive; the Ghani is primarily used in India.[12] The amount of oil extracted using these methods

Vegetable oil 22

varies widely, as shown in the following table for extracting mowrah butter in India:[13]

Method Percentage extracted

Ghani[14] 20–30%

Expellers 34–37%

Solvent 40–43%

Solvent extractionThe processing vegetable oil in commercial applications is commonly done by chemical extraction, using solventextracts, which produces higher yields and is quicker and less expensive. The most common solvent ispetroleum-derived hexane. This technique is used for most of the "newer" industrial oils such as soybean and cornoils.Supercritical carbon dioxide can be used as a non-toxic alternative to other solvents.[15]

HydrogenationOils may be partially hydrogenated to produce various ingredient oils. Lightly hydrogenated oils have very similarphysical characteristics to regular soy oil, but are more resistant to becoming rancid. Margarine oils need to bemostly solid at 32 °C (90 °F) so that the margarine does not melt in warm rooms, yet it needs to be completely liquidat 37 °C (98 °F), so that it doesn't leave a "lardy" taste in the mouth.Hardening vegetable oil is done by raising a blend of vegetable oil and a catalyst in near-vacuum to very hightemperatures, and introducing hydrogen. This causes the carbon atoms of the oil to break double-bonds with othercarbons, each carbon forming a new single-bond with a hydrogen atom. Adding these hydrogen atoms to the oilmakes it more solid, raises the smoke point, and makes the oil more stable.Hydrogenated vegetable oils differ in two major ways from other oils which are equally saturated. Duringhydrogenation, it is easier for hydrogen to come into contact with the fatty acids on the end of the triglyceride, andless easy for them to come into contact with the center fatty acid. This makes the resulting fat more brittle than atropical oil; soy margarines are less "spreadable". The other difference is that trans fatty acids (often called trans fat)are formed in the hydrogenation reactor, and may amount to as much as 40 percent by weight of a partiallyhydrogenated oil. Hydrogenated oils, especially partially hydrogenated oils with their higher amounts of trans fattyacids are increasingly thought to be unhealthy.

SpargingIn the processing of edible oils, the oil is heated under vacuum to near the smoke point, and water is introduced atthe bottom of the oil. The water immediately is converted to steam, which bubbles through the oil, carrying with itany chemicals which are water-soluble. The steam sparging removes impurities that can impart unwanted flavors andodors to the oil.

Particular oilsFor a more comprehensive list, see List of vegetable oils.The following triglyceride vegetable oils account for almost all worldwide production, by volume. All are used asboth cooking oils and as SVO or to make biodiesel. According to the USDA, the total world consumption of majorvegetable oils in 2007/08 was:[16]

Vegetable oil 23

Oil source World consumption(million metric tons)

Notes

Palm 41.31 The most widely produced tropical oil, also used to make biofuel

Soybean 41.28 Accounts for about half of worldwide edible oil production

Rapeseed 18.24 One of the most widely used cooking oils, canola is a variety (cultivar) of rapeseed

Sunflower seed 9.91 A common cooking oil, also used to make biodiesel

Peanut 4.82 Mild-flavored cooking oil

Cottonseed 4.99 A major food oil, often used in industrial food processing

Palm kernel 4.85 From the seed of the African palm tree

Coconut 3.48 Used in soaps and cooking

Olive 2.84 Used in cooking, cosmetics, soaps and as a fuel for traditional oil lamps

Note that these figures include industrial and animal feed use. The majority of European rapeseed oil production isused to produce biodiesel, or used directly as fuel in diesel cars which may require modification to heat the oil toreduce its higher viscosity. The suitability of the fuel should come as little surprise, as Rudolf Diesel originallydesigned his engine to run on peanut oil.Other significant triglyceride oils include:• Corn oil, one of the most common cooking oils. As of 2006 the US produced about 1.09 million metric tons [17]of

corn oil, which is used for cooking oil, salad dressing, margarine, mayonaise, prepared goods like spaghetti sauceand baking mixes, and to fry prepared foods like potato chips and french fries.

• Grape seed oil, used in cooking and cosmetics• Hazelnut and other nut oils• Linseed oil, from flax seeds• Rice bran oil, from rice grains• Safflower oil, a flavorless and colorless cooking oil• Sesame oil, used as a cooking oil, and as a massage oil, particularly in India

History in North AmericaWhile olive oil and other pressed oils have been around for millennia, Procter & Gamble researchers were innovatorswhen they started selling cottonseed oil as a creamed shortening, in 1911. Ginning mills were happy to havesomeone haul away the cotton seeds. Procter & Gamble researchers learned how to extract the oil, refine it, partiallyhydrogenate it (causing it to be solid at room temperature and thus mimic natural lard), and can it under nitrogen gas.Compared to the rendered lard Procter & Gamble was already selling to consumers, Crisco was cheaper, easier to stirinto a recipe, and could be stored at room temperature for two years without turning rancid. (Procter & Gamble soldtheir fats and oils brands – Jif and Crisco – to The J.M. Smucker Co. in 2002.)Soybeans were an exciting new crop from China in the 1930s. Soy was protein-rich, and the medium viscosity oilwas high in polyunsaturates. Henry Ford established a soybean research laboratory, developed soybean plastics and asoy-based synthetic wool, and built a car "almost entirely" out of soybeans.[18] Roger Drackett had a successful newproduct with Windex, but he invested heavily in soybean research, seeing it as a smart investment.[19] By the 1950sand 1960s, soybean oil had become the most popular vegetable oil in the US.In the mid-1970s, Canadian researchers developed a low-erucic-acid rapeseed cultivar. Because the word "rape" was not considered optimal for marketing, they coined the name "canola" (from "Canada Oil low acid"). The U.S. Food and Drug Administration approved use of the canola name in January 1985,[20] and U.S. farmers started planting large areas that spring. Canola oil is lower in saturated fats, and higher in monounsaturates and is a better source of

Vegetable oil 24

omega-3 fats than other popular oils. Canola is very thin (unlike corn oil) and flavorless (unlike olive oil), so itlargely succeeds by displacing soy oil, just as soy oil largely succeeded by displacing cottonseed oil.

Used oilA large quantity of used vegetable oil is produced and recycled, mainly from industrial deep fryers in potatoprocessing plants, snack food factories and fast food restaurants.Recycled oil has numerous uses, including use as a direct fuel, as well as in the production of biodiesel, soap, animalfeed, pet food, detergent, and cosmetics. It's traded as the commodity, yellow grease.Since 2002, an increasing number of European Union countries have prohibited the inclusion of recycled vegetableoil from catering in animal feed. Used cooking oils from food manufacturing, however, as well as fresh or unusedcooking oil, continue to be used in animal feed.[21]

Negative health effectsHydrogenated oils have been shown to cause what is commonly termed the "double deadly effect", raising the levelof LDLs and decreasing the level of HDLs in the blood, increasing the risk of blood clotting inside blood vessels.[22]

A high consumption of omega-6 polyunsaturated fatty acids (PUFAs), which are found in most types of vegetable oil(e.g. soybean oil, corn oil – the most consumed in USA, sunflower oil, etc.) may increase the likelihood thatpostmenopausal women will develop breast cancer.[23] A similar effect was observed on prostate cancer in mice.[24]

Plant based oils high in monounsaturated fatty acids, such as olive oil, peanut oil, and canola oil are relatively low inomega-6 PUFAs and can be used in place of high-polyunsaturated oils.

Product labelingThere is increasing concern that the product labeling that includes "vegetable fat" or "vegetable oil" in its list ofingredients masks the identity of the fats or oils present. This has been made more pressing as concerns have beenraised over the social and environmental impact of palm oil in particular, especially given the predominance of palmoil.[25]

Notes and references[1] "4,000-year-old 'kitchen' unearthed in Indiana" (http:/ / www. stonepages. com/ news/ archives/ 001708. html). Archaeo News. January 26,

2006. . Retrieved 2011-12-30.[2] Parwez Saroj. The Pearson Guide to the B.Sc. (Nursing) Entrance Examination. Pearson Education India. p. 109. ISBN 81-317-1338-5.[3] Robin Dand (1999). The International Cocoa Trade. Woodhead Publishing. p. 169. ISBN 1-85573-434-6.[4] Compare, for example, the list of raw materials from which essential oils are extracted[5] "4,000-year-old 'kitchen' unearthed in Indiana" (http:/ / www. stonepages. com/ news/ archives/ 001708. html). Archaeo News. January 26,

2006. . Retrieved 2006-07-31.[6] "Margarine" (http:/ / www. accessdata. fda. gov/ scripts/ cdrh/ cfdocs/ cfcfr/ CFRSearch. cfm?CFRPart=166& showFR=1). Code of Federal

Regulations Title 21, Chapter I, Subchapter B, Part 166. U.S. Food and Drug Administration. April 1, 2011. . Retrieved 2011-11-01.[7] Linda McGraw (April 19, 2000). "Biodegradable Hydraulic Fluid Nears Market" (http:/ / www. ars. usda. gov/ is/ pr/ 2000/ 000419. htm).

USDA. . Retrieved 2006-09-29.[8] "Cass Scenic Railroad, West Virginia" (http:/ / www. gwrranci. org/ gallery/ 20060824/ ). GWWCA. . Retrieved 2011-11-01.[9] "Ingredients to avoid" (http:/ / www. dogfoodproject. com/ index. php?page=badingredients). The Dog Food Project. . Retrieved 2007-06-26.[10] National Non-Food Crops Centre. GHG Benefits from Use of Vegetable Oils for Electricity, Heat, Transport and Industrial Purposes,

NNFCC 10-016 (http:/ / www. nnfcc. co. uk/ tools/ghg-benefits-from-use-of-vegetable-oils-for-electricity-heat-transport-and-industrial-purposes-nnfcc-10-016)

[11] "Kalu (oil presser)" (http:/ / banglapedia. search. com. bd/ HT/ K_0050. htm). Banglapedia. . Retrieved 2006-11-12.[12] Janet Bachmann. "Oilseed Processing for Small-Scale Producers" (http:/ / www. attra. org/ attra-pub/ oilseed. html). . Retrieved 2006-07-31.[13] B.L. Axtell from research by R.M. Fairman (1992). "Illipe" (http:/ / www. fao. org/ es/ faodef/ fdef14e. htm). Minor oil crops. FAO. .

Retrieved 2006-11-12.

Vegetable oil 25

[14] "Ghani" (http:/ / banglapedia. search. com. bd/ HT/ G_0089. htm). Banglapedia. . Retrieved 2006-11-12. A ghani is a traditional Indian oilpress, driven by a horse or ox.

[15] Eisenmenger, Michael; Dunford, Nurhan T.; Eller, Fred; Taylor, Scott; Martinez, Jose (2006). "Pilot-scale supercritical carbon dioxideextraction and fractionation of wheat germ oil". Journal of the American Oil Chemists' Society 83 (10): 863. doi:10.1007/s11746-006-5038-6.

[16] January 2009 (http:/ / www. fas. usda. gov/ oilseeds/ circular/ 2009/ January/ Oilseedsfull0109. pdf). Oilseeds: World Market and Trade.FOP 1-09. USDA. 2009-01-12. ., Table 03: Major Vegetable Oils: World Supply and Distribution at Oilseeds: World Markets and TradeMonthly Circular (http:/ / www. fas. usda. gov/ oilseeds/ circular/ Current. asp)

[17] Corn Refiners Association. Corn Oil (http:/ / www. corn. org/ wp-content/ uploads/ 2009/ 12/ CornOil. pdf) 5th Edition. 2006[18] "Soybean Car" (http:/ / www. thehenryford. org/ research/ soybeancar. aspx). Popular Research Topics. Benson Ford Research Center. .

Retrieved 2006-10-23.[19] Horstman, Barry M (1999-05-21). "Philip W. Drackett: Earned profits, plaudits" (http:/ / web. archive. org/ web/ 20051205202014/ http:/ /

www. cincypost. com/ living/ 1999/ drack052199. html). The Cincinnati Post (E. W. Scripps Company). Archived from the original (http:/ /www. cincypost. com/ living/ 1999/ drack052199. html) on 2005-12-05. . Retrieved 2006-10-22.

[20] "Canola oil" (http:/ / web. archive. org/ web/ 20060617234030/ http:/ / www. fda. gov/ bbs/ topics/ ANSWERS/ ANS00198. html).Archived from the original (http:/ / www. fda. gov/ bbs/ topics/ ANSWERS/ ANS00198. html) on 2006-06-17. . Retrieved 2006-07-31.

[21] "Waste cooking oil from catering premises" (http:/ / www. food. gov. uk/ foodindustry/ guidancenotes/ foodguid/ wastecookingoil). .Retrieved 2006-07-31.

[22] "Vegetable Oil – Everything You Need To Know About Vegetable Oils" (http:/ / vegetableoils. org/ vegetableoil/ ). .[23] Emily Sonestedt, Ulrika Ericson, Bo Gullberg, Kerstin Skog, Håkan Olsson, Elisabet Wirfält (2008). "Do both heterocyclic amines and

omega-6 polyunsaturated fatty acids contribute to the incidence of breast cancer in postmenopausal women of the Malmö diet and cancercohort?". The International Journal of Cancer (UICC International Union Against Cancer) 123 (7): 1637–1643. doi:10.1002/ijc.23394.PMID 18636564.

[24] Berquin IM, Min Y, Wu R, et al. (July 2007). "Modulation of prostate cancer genetic risk by omega-3 and omega-6 fatty acids". The Journalof Clinical Investigation 117 (7): 1866–75. doi:10.1172/JCI31494. PMC 1890998. PMID 17607361.

[25] An issue highlighted in documentaries such as Dying for a Biscuit on BBC Panorama http:/ / www. bbc. co. uk/ programmes/ b00r4t3s

Other references• Beare-Rogers, J.L. (1983). H.H. Draper. ed. "Trans and positional isomers of common fatty acids". Advances in

Nutritional Research (Plenum Press, New York) 5: 171–200. PMID 6342341.• Berry, E.M. and Hirsch, J. (1986). "Does dietary linolenic acid influence blood pressure?". American Journal of

Clinical Nutrition 44: 336–340.• Beyers, E.C. and Emken, E.A. (1991). "Metabolites of cis, trans, and trans, cis isomers of linoleic acid in mice

and incorporation into tissue lipids". Biochimica et Biophysica Acta 1082: 275–284.• Birch, D.G., Birch, E.E., Hoffman, D.R., and Uauy, R.D. (1992). "Retinal development in very-low-birth-weight

infants fed diets differing in omega-3 fatty acids". Investigative Ophthalmology and Visual Science 33 (8):2365–2376.

• Birch, E.E., Birch, D.G., Hoffman, D.R., and Uauy, R. (1992). "Dietary essential fatty acid supply and visualacuity development". Investigative Ophthalmology and Visual Science 33 (11): 3242–3253.

• Brenner, R.R. (1989). A.J. Vergroesen and M. Crawford. ed. Factors influencing fatty acid chain elongation anddesaturation, in the role of fats in human nutrition (2 ed.). Academic Press, London. pp. 45–79.

•• "Report of the task force on trans fatty acids". British Nutrition Foundation. 1987.•• "Central Soya annual report". 1979.• Emken, E. A. (1984). "Nutrition and biochemistry of trans and positional fatty acid isomers in hydrogenated oils".

Annual Reviews of Nutrition 4: 339–376.• Enig, M.G., Atal, S., Keeney, M and Sampugna, J. (1990). "Isomeric trans fatty acids in the U.S. diet". Journal of

the American College of Nutrition 9: 471–486.• Ascherio, A., Hennekens, C.H., Baring, J.E., Master, C., Stampfer, M.J. and Willett, W.C. (1994). "Trans fatty

acids intake and risk of myocardial infarction". Circulation 89: 94–101.• Gurr, M.I. (1983). "Trans fatty acids: Metabolic and nutritional significance". Bulletin of the International Dairy

Federation 166: 5–18.• Hui Y. H., ed. Bailey's Industrial Oil and Fat Products.

Vegetable oil 26

• Koletzko, B. (1992). "Trans fatty acids may impair biosynthesis of long-chain polyunsaturates and growth inman". Acta Paediatrica 81: 302–306.

• Lief, Alfred (1958). It floats: The story of Procter & Gamble. Rinehart.• MacMillen, Harold W. (1967). Mr. Mac and Central Soya: the foodpower story. Newcomen Society.• Marchand, C.M. (1982). "Positional isomers of trans-octadecenoic acids in margarine". Canadian Institute of

Food Science and Technology Journal 15: 196–199.• Mensink, R.P., Zock, P.L., Katan, M.B. and Hornstra, G. (1992). "Effect of dietary cis-and trans-fatty acids on

serum lipoprotein[a] levels in humans". Journal of Lipid Research 33: 1493–1501.• Siguel, E.N. and Lerman, R.H. (1993). "Trans fatty acid patterns in patients with angiographically documented

coronary artery disease". American Journal of Cardiology 71: 916–920.• Troisi, R., Willett, W.C. and Weiss, S.T. (1992). "Trans-fatty acid intake in relation to serum lipid concentrations

in adult men". American Journal of Clinical Nutrition 56: 1019–1024.• Willett, W.C., Stampfer, M.J., Manson, J.E., Colditz, G.A., Speizer, F.E., Rosner, B.A., Sampson, L.A. and

Hennekens, C.H. (1993). "Intake of trans fatty acids and risk of coronary heart disease among women". TheLancet 341: 581–585.

Further reading• Gupta, Monoj K. (2007). Practical guide for vegetable oil processing. AOCS Press, Urbana, Illinois.

ISBN 978-1-893997-90-5.• Jee, Michael, ed. (2002). Oils and Fats Authentication. Blackwell Publishing, Oxford, England.

ISBN 1-84127-330-9.• Salunkhe, D.K., Chavan, J.K., Adsule, R.N. and Kadam, S.S. (1992). World Oilseeds – Chemistry, Technology,

and Utilization. Van Nostrand Reinhold, New York. ISBN 0-442-00112-6.

External links• "Fats and Cholesterol: Out with the Bad, In with the Good – What Should You Eat? – The Nutrition Source –

Harvard School of Public Health" (http:/ / www. hsph. harvard. edu/ nutritionsource/ what-should-you-eat/fats-full-story/ index. html). www.hsph.harvard.edu. Retrieved 2009-05-04.

• "Vegetable oil yields, characteristics: Journey to Forever" (http:/ / journeytoforever. org/ biodiesel_yield. html).journeytoforever.org. Retrieved 2009-05-04.

• "National Non-Food Crops Centre" (http:/ / www. nnfcc. co. uk/ ). www.nnfcc.co.uk. Retrieved 2009-05-04.

Fat 27

FatFats consist of a wide group of compounds that are generally soluble in organic solvents and generally insoluble inwater. Chemically, fats are triglycerides, triesters of glycerol and any of several fatty acids. Fats may be either solidor liquid at room temperature, depending on their structure and composition. Although the words "oils", "fats", and"lipids" are all used to refer to fats, "oils" is usually used to refer to fats that are liquids at normal room temperature,while "fats" is usually used to refer to fats that are solids at normal room temperature. "Lipids" is used to refer toboth liquid and solid fats, along with other related substances, usually in a medical or biochemical context. The word"oil" is also used for any substance that does not mix with water and has a greasy feel, such as petroleum (or crudeoil), heating oil, and essential oils, regardless of its chemical structure.[1]

Fats form a category of lipid, distinguished from other lipids by their chemical structure and physical properties. Thiscategory of molecules is important for many forms of life, serving both structural and metabolic functions. They arean important part of the diet of most heterotrophs (including humans). Fats or lipids are broken down in the body byenzymes called lipases produced in the pancreas.Examples of edible animal fats are lard, fish oil, butter/ghee and whale blubber. They are obtained from fats in themilk and meat, as well as from under the skin, of an animal. Examples of edible plant fats include peanut, soya bean,sunflower, sesame, coconut and olive oils, and cocoa butter. Vegetable shortening, used mainly for baking, andmargarine, used in baking and as a spread, can be derived from the above oils by hydrogenation.These examples of fats can be categorized into saturated fats and unsaturated fats. Unsaturated fats can be furtherdivided into cis fats, which are the most common in nature, and trans fats, which are rare in nature but present inpartially hydrogenated vegetable oils.

Chemical structure

A triglyceride molecule

There are many different kinds of fats, but each is avariation on the same chemical structure. All fats arederivatives of fatty acids and glycerol. The moleculesare called triglycerides, which are triesters of glycerol(an ester being the molecule formed from the reactionof the carboxylic acid and an organic alcohol). As asimple visual illustration, if the kinks and angles ofthese chains were straightened out, the molecule wouldhave the shape of a capital letter E. The fatty acidswould each be a horizontal line; the glycerol"backbone" would be the vertical line that joins thehorizontal lines. Fats therefore have "ester" bonds.

The properties of any specific fat molecule depend onthe particular fatty acids that constitute it. Differentfatty acids are composed of different numbers of carbon and hydrogen atoms. The carbon atoms, each bonded to twoneighboring carbon atoms, form a zigzagging chain; the more carbon atoms there are in any fatty acid, the longer itschain will be. Fatty acids with long chains are more susceptible to intermolecular forces of attraction (in this case,van der Waals forces), raising its melting point. Long chains also yield more energy per molecule when metabolized.

Fat 28

Saturated and unsaturated fatsA fat's constituent fatty acids may also differ in the C/H ratio. When all three fatty acids have the formulaCnH(2n+1)CO2H, the resulting fat is called "saturated". Values of n usually range from 13 to 17. Each carbon atom inthe chain is saturated with hydrogen, meaning they are bonded to as many hydrogens as possible. Unsaturated fatsare derived from fatty acids with the formula CnH(2n-1)CO2H. These fatty acids contain double bonds within carbonchain. This results in an "unsaturated" fatty acid. More specifically, it would be a monounsaturated fatty acid.Polyunsaturated fatty acids would be fatty acids with more than one double bond; they have the formula,CnH(2n-3)CO2H and CnH(2n-5)CO2H. Unsaturated fats can be converted to saturated ones by the process ofhydrogenation. This technology underpinned the development of margarine.Saturated and unsaturated fats differ in their energy content and melting point. Since unsaturated fats contain fewercarbon-hydrogen bonds than saturated fats with the same number of carbon atoms, unsaturated fats will yield slightlyless energy during metabolism than saturated fats with the same number of carbon atoms. Saturated fats can stackthemselves in a closely packed arrangement, so they can freeze easily and are typically solid at room temperature.For example, animal fats tallow and lard are high in saturated fatty acid content and are solids. Olive and linseed oilson the other hand are highly unsaturated and are oily.

Trans fatsThere are two ways the double bond may be arranged: the isomer with both parts of the chain on the same side of thedouble bond (the cis-isomer), or the isomer with the parts of the chain on opposite sides of the double bond (thetrans-isomer). Most trans-isomer fats (commonly called trans fats) are commercially produced. Trans fatty acids arerare in nature. The cis-isomer introduces a kink into the molecule that prevents the fats from stacking efficiently as inthe case of fats with saturated chains. This decreases intermolecular forces between the fat molecules, making itmore difficult for unsaturated cis-fats to freeze; they are typically liquid at room temperature. Trans fats may stillstack like saturated fats, and are not as susceptible to metabolization as other fats. Trans fats may significantlyincrease the risk of coronary heart disease.[2]

Importance for living organismsVitamins A, D, E, and K are fat-soluble, meaning they can only be digested, absorbed, and transported inconjunction with fats. Fats are also sources of essential fatty acids, an important dietary requirement.Fats play a vital role in maintaining healthy skin and hair, insulating body organs against shock, maintaining bodytemperature, and promoting healthy cell function.Fats also serve as energy stores for the body, containing about 37.8 kilojoules (9 calories) per gram of fat.[3] They arebroken down in the body to release glycerol and free fatty acids. The glycerol can be converted to glucose by theliver and thus used as a source of energy.Fat also serves as a useful buffer towards a host of diseases. When a particular substance, whether chemical orbiotic—reaches unsafe levels in the bloodstream, the body can effectively dilute—or at least maintain equilibriumof—the offending substances by storing it in new fat tissue. This helps to protect vital organs, until such time as theoffending substances can be metabolized and/or removed from the body by such means as excretion, urination,accidental or intentional bloodletting, sebum excretion, and hair growth.While it is nearly impossible to remove fat completely from the diet, it would also be unhealthy to do so. Some fattyacids are essential nutrients, meaning that they can't be produced in the body from other compounds and need to beconsumed in small amounts. All other fats required by the body are non-essential and can be produced in the bodyfrom other compounds.

Fat 29

Adipose tissue

The obese mouse on the left has large stores ofadipose tissue. For comparison, a mouse with a

normal amount of adipose tissue is shown on theright.

In animals, adipose, or fatty tissue is the body's means of storingmetabolic energy over extended periods of time. Depending on currentphysiological conditions, adipocytes store fat derived from the diet andliver metabolism or degrade stored fat to supply fatty acids and alsoglycerol to the circulation. These metabolic activities are regulated byseveral hormones (i.e., insulin, glucagon and epinephrine). Thelocation of the tissue determines its metabolic profile: "visceral fat" islocated within the abdominal wall (i.e., beneath the wall of abdominalmuscle) whereas "subcutaneous fat" is located beneath the skin (andincludes fat that is located in the abdominal area beneath the skin butabove the abdominal muscle wall). Visceral fat was recentlydiscovered to be a significant producer of signaling chemicals (i.e.,hormones), among which are several which are involved in inflammatory tissue responses. One of these is resistinwhich has been linked to obesity, insulin resistance, and Type 2 diabetes. This latter result is currently controversial,and there have been reputable studies supporting all sides on the issue.

References[1] Maton, Anthea; Jean Hopkins, Charles William McLaughlin, Susan Johnson, Maryanna Quon Warner, David LaHart, Jill D. Wright (1993).

Human Biology and Health. Englewood Cliffs, New Jersey, USA: Prentice Hall. ISBN 0-13-981176-1. OCLC 32308337.[2] Mozaffarian D, Katan MB, Ascherio A, Stampfer MJ, Willett WC (13 April 2006). "Trans Fatty Acids and Cardiovascular Disease". New

England Journal of Medicine 354 (15): 1601–1613. doi:10.1056/NEJMra054035. PMID 16611951.[3] Stern, David P. (May 19, 2008). Newtonian mechanics – (15) Energy (http:/ / www-istp. gsfc. nasa. gov/ stargaze/ Senergy. htm). From

Stargazers to Starships. Retrieved April 11, 2011 from NASA's International Solar-Terrestrial Physics Goddard Space Flight Center website.

• Donatelle, Rebecca J. (2005). Health, the Basics (6th ed.). San Francisco: Pearson Education, Inc.ISBN 0-13-120687-7. OCLC 51801859.

Further reading• Hayes, K.C. (May 2005). Dietary fat and blood lipids (http:/ / people. brandeis. edu/ ~kchayes/ bginfo. html).

Retrieved March 10, 2011.

Animal fat 30

Animal fat

Lard

Wet-rendered lard, from pork fatback.

Fat composition

Saturated fats 38–43%:Palmitic acid: 25–28%Stearic acid: 12–14%Myristic acid: 1%

Unsaturated fats 56–62%

Monounsaturated fats 47–50%:Oleic acid: 44–47%Palmitoleic acid: 3%

Polyunsaturated fats Linoleic acid: 6–10%[1]

Properties

Food energy per 100g 3770 kJ (900 kcal)

Melting point backfat: 30–40 °C (86–104 °F)leaf fat: 43–48 °C (109–118 °F)mixed fat: 36–45 °C (97–113 °F)

Smoke point 121–218 °C (250–424 °F)

Specific gravity at 20 °C 0.917–0.938

Iodine value 45–75

Acid value 3.4

Saponification value 190–205

Unsaponifiable 0.8%

Animal fats and oils are lipid materials derived from animals. Physically, oils are liquid at room temperature, andfats are solid. Chemically, both fats and oils are composed of triglycerides. Although many animal parts andsecretions may yield oil, in commercial practice, oil is extracted primarily from rendered tissue fats obtained fromlivestock animals like pigs, chickens and cows. Dairy products also yield popular animal fat and oil products such ascheese, butter, and milk.Flesh and animal fat have a melting temperature of 184 °C, a boiling point of around 200 °C and an ignition point of 280 °C where it will burst into flames without spark.[2] Certain substances such as goose fat produce a higher smoke

Animal fat 31

point than other animal fats, but are still lower than many vegetable oils such as olive or avocado. [3]

In consumer meat products in the U.S., animal remains are found to be classified as Animal fats once the particlesize of bone solids is more than 3 percent, protein content is less than 14 percent and or the product contains over 30percent pure fat content.[4]

Animal fats are commonly consumed as part of a western diet in their semi-solid form as either milk, butter, lard,schmaltz, and dripping or more commonly as filler in factory produced meat, pet food and fast-food products.[5]

Dairy products are animal secretions which contain varying levels of water, oils, fats and animal cells fromcirculatory and lymphatic systems such as blood and mammary glands.

Culinary usesMany animal fats and oils are consumed directly, or indirectly as ingredients in food. The oils serve a number ofpurposes in this role:• Shortening – to give pastry a crumbly texture.• Texture – oils can serve to make other ingredients stick together less.• Flavor – some may be chosen specifically for the flavor they impart.• Flavor base – oils can also "carry" flavors of other ingredients, since many flavors are present in chemicals that

are soluble in oil.Secondly, oils can be heated, and used to cook other foods. Oils suitable for this purpose must have a high flashpoint.

References[1] National Research Council. (1976). Fat Content and Composition of Animal Products. (http:/ / books. nap. edu/ openbook.

php?chapselect=yo& page=203& record_id=22& Jump+ to+ Specified+ Page. x=0& Jump+ to+ Specified+ Page. y=0); p. 203. Washington,DC: Printing and Publishing Office, National Academy of Science. ISBN 0-309-02440-4

[2] Combustion Experiments with Flesh and Animal Fat (http:/ / vho. org/ tr/ 2004/ 1/ Mattogno64-72. html), VHO.org, 2004-01-01, , retrieved2012-03-16

[3] The Goose Fat Information Service (http:/ / www. goosefat. co. uk/ page/ usage-recipes), Goosefat.co.uk/, 2012-03-19, , retrieved 2012-03-19[4] Definitions and Standards of Identity (http:/ / www. fda. gov/ Food/ FoodSafety/ RetailFoodProtection/ FoodCode/ FoodCode2001/

ucm092709. htm), FDA.gov, 1978-06-13, , retrieved 2012-03-16[5] Meat Products with High Levels of Extenders and Fillers (http:/ / www. fao. org/ docrep/ 010/ ai407e/ AI407E16. htm), Food and

Agricultural Organization of the United States, , retrieved 2012-03-16

Saturated fat 32

Saturated fatSaturated fat is fat that consists of triglycerides containing only saturated fatty acids. Saturated fatty acids have nodouble bonds between the individual carbon atoms of the fatty acid chain. That is, the chain of carbon atoms is fully"saturated" with hydrogen atoms. There are many kinds of naturally occurring saturated fatty acids, which differmainly in number of carbon atoms, from 3 carbons (propionic acid) to 36 (hexatriacontanoic acid).Various fats contain different proportions of saturated and unsaturated fat. Examples of foods containing a highproportion of saturated fat include animal fats such as cream, cheese, butter, and ghee; suet, tallow, lard, and fattymeats; as well as certain vegetable products such as coconut oil, cottonseed oil, palm kernel oil, chocolate, and manyprepared foods.[1]

Fat profilesWhile nutrition labels regularly combine them, the saturated fatty acids appear in different proportions among foodgroups. Lauric and myristic acids are most commonly found in "tropical" oils (e.g., palm kernel, coconut) and dairyproducts. The saturated fat in meat, eggs, chocolate, and nuts is primarily the triglycerides of palmitic and stearicacids.

Saturated fat profile of common foods; Esterified fatty acids as percentage of total fat[2]

Food Lauric acid Myristic acid Palmitic acid Stearic acid

Coconut oil 47% 18% 9% 3%

Palm oil 0.1% 1% 44% 5%

Butter 3% 11% 29% 13%

Ground beef 0% 4% 26% 15%

Dark chocolate 0% 1% 34% 43%

Salmon 0% 1% 29% 3%

Eggs 0% 0.3% 27% 10%

Cashews 2% 1% 10% 7%

Soybean oil 0% 0% 11% 4%

Examples of saturated fatty acidsSome common examples of fatty acids:• Butyric acid with 4 carbon atoms (contained in butter)• Lauric acid with 12 carbon atoms (contained in coconut oil, palm kernel oil, and breast milk)• Myristic acid with 14 carbon atoms (contained in cow's milk and dairy products)• Palmitic acid with 16 carbon atoms (contained in palm oil and meat)• Stearic acid with 18 carbon atoms (also contained in meat and cocoa butter)

Saturated fat 33

Association with diseasesSince the 1950s, it has been commonly believed that consumption of foods containing high amounts of saturatedfatty acids (including meat fats, milk fat, butter, lard, coconut oil, palm oil, and palm kernel oil) is potentially lesshealthy than consuming fats with a lower proportion of saturated fatty acids. Sources of lower saturated fat buthigher proportions of unsaturated fatty acids include olive oil, peanut oil, canola oil, avocados, safflower, corn,sunflower, soy, and cottonseed oils.[3]

Cardiovascular diseaseMedical, heart-health, and governmental authorities, such as the World Health Organization,[4] the AmericanDietetic Association,[5] the Dietitians of Canada,[5], the British Dietetic Association,[6] American HeartAssociation,[7] the British Heart Foundation,[8] the World Heart Federation,[9], the British National HealthService,[10] the United States Food and Drug Administration, [11] and the European Food Safety Authority[12] advisethat saturated fat is a risk factor for cardiovascular disease (CVD).Numerous systematic reviews have examined the relationship between saturated fat and cardiovascular disease:

Systematicreview

Relationships between cardiovascular disease and saturated fatty acids (SFA)

Hooper,2011[13]

Reducing saturated fat in diets reduced the risk of having a cardiovascular event by 14 percent (no reduction in mortality).

Mozaffarian,2010[14]

These findings provide evidence that consuming polyunsaturated fats (PUFA) in place of SFA reduces Coronary Heart Disease(CHD) events in RCTs. Replacing saturated fats with PUFAs as percentage of calories strongly reduced CHD mortality

Siri-Tarino,2010[15]

5–23 years of follow-up of 347,747 subjects, 11,006 developed CHD or stroke. A meta-analysis of prospective epidemiologicstudies showed that there is no significant evidence for concluding that dietary saturated fat is associated with an increased risk ofCHD or CVD.

Danaei,2009[16]

Low PUFA intake has an 1-5% Increased risk of ischemic heart disease: Low dietary PUFA (in replacement of SFA). age 30–44Increase in RR 1.05.

Mente,2009[17]

Single-nutrient RCTs have yet to evaluate whether reducing saturated fatty acid intake lowers the risk of CHD events. Forpolyunsaturated fatty acid intake, most of the RCTs have not been adequately powered and did not find a significant reduction inCHD outcomes.

Skeaff,2009[18]

Intake of SFA was not significantly associated with CHD mortality, with a RR of 1.14. Moreover, there was no significantassociation with CHD death. Intake of PUFA was strongly significantly associated with CHD mortality, with a RR of 1.25. TheHealth Professionals Follow-up Study and the EUROASPIRE study results mirrored those of total PUFA; intake of linoleic acidwas significantly associated with CHD mortality.

Jakobsen,2009[19]

No overall association between saturated fat and coronary heart disease was found. Polyunsaturated fat was inversely associatedwith coronary heart disease among women and men, although not significantly. In conclusion, the present study suggests thatcoronary heart disease risk relates to both the quantity and the quality of dietary fats. "The associations suggest that replacingsaturated fatty acids with polyunsaturated fatty acids rather than monounsaturated fatty acids or carbohydrates prevents CHD overa wide range of intakes."

Van Horn,2008[20]

25-35% fats but <7% SFA and TFA reduces risk

Chanu,2003[21]

significant in longer term

Hooper,2001[22]

Despite decades of effort and many thousands of people randomised, there is still only limited and inconclusive evidence of theeffects of modification of total, saturated, monounsaturated, or polyunsaturated fats on cardiovascular morbidity and mortality.Study conclusion: "There is a small but potentially important reduction in cardiovascular risk with reduction or modification ofdietary fat intake, seen particularly in trials of longer duration."

Saturated fat 34

Hu, 1999[23] Based on the data from the Nurses’ Health Study, we estimated that substitution of the fat from 1 ounce of nuts for equivalentenergy from carbohydrate in an average diet was associated with a 30% reduction in CHD risk and the substitution of nut fat forsaturated fat was associated with 45% reduction in risk.

Truswell,1994[24]

decrease SFA and cholesterol intake, partial replacement with PUFA: 6% reduced deaths, 13% reduced events

While many studies have found that including polyunsaturated fats in the diet in place of saturated fats producesmore beneficial CVD outcomes, the effects of substituting monounsaturated fats or carbohydrates are unclear.[25][26]

Dyslipidemia

The consumption of saturated fat is generally considered a risk factor for dyslipidemia, which in turn is a risk factorfor some types of cardiovascular disease.[27][28][29][30][31]

There are strong, consistent, and graded relationships between saturated fat intake, blood cholesterol levels, and themass occurrence of cardiovascular disease. The relationships are accepted as causal.[32][33] Abnormal blood lipidlevels, that is high total cholesterol, high levels of triglycerides, high levels of low-density lipoprotein (LDL, "bad"cholesterol) or low levels of high-density lipoprotein (HDL, "good" cholesterol) cholesterol all increase the risk ofheart disease and stroke.[9]

Meta-analyses have found a significant relationship between saturated fat and serum cholesterol levels.[34] High totalcholesterol levels, which may be caused by many factors, are associated with an increased risk of cardiovasculardisease.[35][36] However, other indicators measuring cholesterol such as high total/HDL cholesterol ratio are morepredictive than total serum cholesterol.[36] In a study of myocardial infarction in 52 countries, the ApoB/ApoA1(related to LDL and HDL, respectively) ratio was the strongest predictor of CVD among all risk factors.[37] Thereare other pathways involving obesity, triglyceride levels, insulin sensitivity, endothelial function, andthrombogenicity, among others, that play a role in CVD, although it seems, in the absence of an adverse blood lipidprofile, the other known risk factors have only a weak atherogenic effect.[38] Different saturated fatty acids havediffering effects on various lipid levels.[39]

Cancer

Breast cancer

A meta-analysis published in 2003 found a significant positive relationship in both control and cohort studiesbetween saturated fat and breast cancer.[40] However two subsequent reviews have found weak or insignificantassociations of saturated fat intake and breast cancer risk,[41][42] and note the prevalence of confoundingfactors.[41][43]

Colorectal cancer

A systematic literature review published by the World Cancer Research Fund and the American Institute for CancerResearch in 2007 found limited but consistent evidence for a positive relationship between animal fat and colorectalcancer.[44]

Saturated fat 35

Ovarian cancer

A meta-analysis of eight observational studies published in 2001 found a statistically significant positive relationshipbetween saturated fat and ovarian cancer.[45]

Prostate cancer

Further information: Prostate cancer#Oils and fatty acidsSome researchers have indicated that serum myristic acid[46][47] and palmitic acid[47] and dietary myristic[48] andpalmitic[48] saturated fatty acids and serum palmitic combined with alpha-tocopherol supplementation[46] areassociated with increased risk of prostate cancer in a dose-dependent manner. These associations may, however,reflect differences in intake or metabolism of these fatty acids between the precancer cases and controls, rather thanbeing an actual cause.[47]

BonesMounting evidence indicates that the amount and type of fat in the diet can have important effects on bone health.Most of this evidence is derived from animal studies. The data from one study indicated that bone mineral density isnegatively associated with saturated fat intake, and that men may be particularly vulnerable.[49]

Dietary recommendationsRecommendations to reduce or limit dietary intake of saturated fats are made by Health Canada,[50] the USDepartment of Health and Human Services,[51] the UK Food Standards Agency,[52] the Australian Department ofHealth and Aging,[53] the Singapore Government Health Promotion Board,[54] the Indian Government CitizensHealth Portal,[55] the New Zealand Ministry of Health,[56] the Food and Drugs Board Ghana,[57] the Republic ofGuyana Ministry of Health,[58] and Hong Kong's Centre for Food Safety.[59]

A 2004 statement released by the Centers for Disease Control (CDC) determined that "Americans need to continueworking to reduce saturated fat intake…"[60] In addition, reviews by the American Heart Association led theAssociation to recommend reducing saturated fat intake to less than 7% of total calories according to its 2006recommendations.[61][62] This concurs with similar conclusions made by the US Department of Health and HumanServices, which determined that reduction in saturated fat consumption would positively affect health and reduce theprevalence of heart disease.[63]

In 2003, the World Health Organization (WHO) and Food and Agriculture Organization (FAO) expert consultationreport concluded that "intake of saturated fatty acids is directly related to cardiovascular risk. The traditional target isto restrict the intake of saturated fatty acids to less than 10% of daily energy intake and less than 7% for high-riskgroups. If populations are consuming less than 10%, they should not increase that level of intake. Within theselimits, intake of foods rich in myristic and palmitic acids should be replaced by fats with a lower content of theseparticular fatty acids. In developing countries, however, where energy intake for some population groups may beinadequate, energy expenditure is high and body fat stores are low (BMI <18.5 kg/m2). The amount and quality offat supply has to be considered keeping in mind the need to meet energy requirements. Specific sources of saturatedfat, such as coconut and palm oil, provide low-cost energy and may be an important source of energy for thepoor."[64]

Dr. German and Dr. Dillard of University of California and Nestle Research Center in Switzerland, in their 2004review, pointed out that "no lower safe limit of specific saturated fatty acid intakes has been identified" andrecommended that the influence of varying saturated fatty acid intakes against a background of different individuallifestyles and genetic backgrounds should be the focus in future studies.[65]

Blanket recommendations to lower saturated fat were criticized at a 2010 conference debate of the American Dietetic Association for focusing too narrowly on reducing saturated fats rather than emphasizing increased consumption of

Saturated fat 36

healthy fats and unrefined carbohydrates. Concern was expressed over the health risks of replacing saturated fats inthe diet with refined carbohydrates, which carry a high risk of obesity and heart disease, particularly at the expenseof polyunsaturated fats which may have health benefits. None of the panelists recommended heavy consumption ofsaturated fats, emphasizing instead the importance of overall dietary quality to cardiovascular health.[66]

Molecular description

Two-dimensional representation of the saturated fatty acid myristic acid

A space-filling model of the saturated fatty acid myristic acid

It should be noted, as this is thedefining factor of saturated fats, thatthe two-dimensional illustration hasimplicit hydrogens bonded to each ofthe carbon atoms in the polycarbon tailof the myristic acid molecule (there are13 carbons in the tail, 14 carbons in theentire molecule).

Carbon atoms are also implicitlydrawn, as they are portrayed asintersections between two straightlines. "Saturated," in general, refers toa maximum number of hydrogensbonded to each carbon of thepolycarbon tail as allowed by the Octet

Rule. This also means that only single bonds (sigma bonds) will be present between adjacent carbon atoms of thetail.

References[1] Saturated fat food sources (http:/ / www. dietaryfiberfood. com/ fat-saturated. php)[2] "USDA National Nutrient Database for Standard Reference, Release 20" (http:/ / www. ars. usda. gov/ ba/ bhnrc/ ndl). United States

Department of Agriculture. 2007. .[3] "Dietary fats: Know which types to choose" (http:/ / www. mayoclinic. com/ health/ fat/ NU00262). Mayo Clinic. 2011-02-15. . Retrieved

2011-09-02.[4] Joint WHO/FAO Expert Consultation (2003). Diet, Nutrition and the Prevention of Chronic Diseases (WHO technical report series 916)

(http:/ / www. who. int/ hpr/ NPH/ docs/ who_fao_expert_report. pdf). World Health Organization. pp. 81–94. ISBN 92-4-120916-X. .Retrieved 2011-03-11.

[5] Kris-Etherton, PM; Innis, S; American Dietetic, Association; Dietitians Of, Canada (September 2007). "Position of the American DieteticAssociation and Dietitians of Canada: Dietary Fatty Acids" (http:/ / www. dietitians. ca/ Downloadable-Content/ Public/dietaryfats-position-paper. aspx). Journal of the American Dietetic Association 107 (9): 1599–1611. PMID 17936958. . Retrieved 2011-03-18.

[6] "Food Fact Sheet - Cholesterol" (http:/ / www. bda. uk. com/ foodfacts/ cholesterol. pdf). British Dietetic Association. . Retrieved 3 May2012.

[7] "Frequently Asked Questions about Fats" (http:/ / www. heart. org/ HEARTORG/ GettingHealthy/ NutritionCenter/ HealthyDietGoals/Frequently-Asked-Questions-About-Fats_UCM_306069_Article. jsp). American Heart Association. . Retrieved 3 May 2012.

[8] "Saturated Fat" (http:/ / www. bhf. org. uk/ heart-health/ prevention/ healthy-eating/ saturated-fat. aspx). . Retrieved 2012-5-3.[9] "Cardiovascular Disease Risk Factors" (http:/ / www. world-heart-federation. org/ cardiovascular-health/ cardiovascular-disease-risk-factors).

. Retrieved 2012-05-03.[10] "Lower your cholesterol" (http:/ / www. nhs. uk/ livewell/ healthyhearts/ pages/ cholesterol. aspx). National Health Service. . Retrieved

2012-05-03.[11] "Nutrition Facts at a Glance - Nutrients: Saturated Fat" (http:/ / www. fda. gov/ Food/ LabelingNutrition/ ConsumerInformation/

ucm192658. htm). Food and Drug Administration. 2009-12-22. . Retrieved 2012-05-03.[12] "Scientific Opinion on Dietary Reference Values for fats, including saturated fatty acids, polyunsaturated fatty acids, monounsaturated fatty

acids, trans fatty acids, and cholesterol" (http:/ / www. efsa. europa. eu/ en/ efsajournal/ pub/ 1461. htm). European Food Safety Authority. .Retrieved 3 May 2012.

Saturated fat 37

[13] Hooper L, Summerbell CD, Thompson R, Sills D, Roberts FG, Moore H, Smith GD (July 2011). "Reduced or modified dietary fat forpreventing cardiovascular disease". The Cochrane Library (7): CD002137. doi:10.1002/14651858.CD002137.pub2. PMID 21735388.

[14] Mozaffarian D, Micha R, Wallace S (March 2010). Katan, Martijn B.. ed. "Effects on Coronary Heart Disease of Increasing PolyunsaturatedFat in Place of Saturated Fat: A Systematic Review and Meta-Analysis of Randomized Controlled Trials". PLoS Medicine 7 (3): 1–10.doi:10.1371/journal.pmed.1000252. ISSN 1549-1277. PMC 2843598. PMID 20351774.

[15] Siri-Tarino PW, Sun Q, Hu FB, Krauss RM (March 2010). "Meta-analysis of prospective cohort studies evaluating the association ofsaturated fat with cardiovascular disease". The American Journal of Clinical Nutrition 91 (3): 535–46. doi:10.3945/ajcn.2009.27725.PMC 2824152. PMID 20071648.

[16] Danaei G et al. (April 2009). Hales, Simon. ed. "The Preventable Causes of Death in the United States: Comparative Risk Assessment ofDietary, Lifestyle, and Metabolic Risk Factors" (http:/ / www. plosmedicine. org/ article/ fetchObjectAttachment. action?uri=info:doi/ 10.1371/ journal. pmed. 1000058& representation=PDF). PLoS Medicine 6 (4): e1000058. doi:10.1371/journal.pmed.1000058. ISSN 1549-1277.PMC 2667673. PMID 19399161. . Retrieved 2011-03-24.

[17] Mente A, de Koning L, Shannon HS, Anand SS (April 2009). "A systematic review of the evidence supporting a causal link between dietaryfactors and coronary heart disease" (http:/ / archinte. ama-assn. org/ cgi/ content/ full/ 169/ 7/ 659). Arch. Intern. Med. 169 (7): 659–69.doi:10.1001/archinternmed.2009.38. PMID 19364995. .

[18] Skeaff, Murray; Miller, Jody (15 September 2009). "Dietary fat and coronary heart disease: Summary of evidence from prospective cohortand randomised controlled trials" (http:/ / content. karger. com/ ProdukteDB/ produkte. asp?Aktion=ShowPDF& ArtikelNr=229002&Ausgabe=250361& ProduktNr=223977& filename=229002. pdf). Annals of nutrition & metabolism 55 (1–3): 173–U287.doi:10.1159/000229002. ISSN 0250-6807. . Retrieved 2011-03-12.

[19] Jakobsen, MU; O'Reilly, EJ; Heitmann, BL; Pereira, MA; Bälter, K; Fraser, GE; Goldbourt, U; Hallmans, G et al. (2009). "Major types ofdietary fat and risk of coronary heart disease: a pooled analysis of 11 cohort studies". The American journal of clinical nutrition 89 (5):1425–32. doi:10.3945/ajcn.2008.27124. PMC 2676998. PMID 19211817.

[20] Van Horn L et al (February 2008). "The evidence for dietary prevention and treatment of cardiovascular disease". Journal of the AmericanDietetic Association 108 (2): 287–331. doi:10.1016/j.jada.2007.10.050. ISSN 0002-8223. PMID 18237578.

[21] Chanu B (September 2003). "Primary dietetic prevention of ischaemic heart disease". Archives des Maladies du Coeur et des Vaisseux 96(Sp. Iss. 6): 21–25. ISSN 0003-9683.

[22] Hooper, L et al. (31 Mar 2001). "Dietary fat intake and prevention of cardiovascular disease: systematic review". British Medical Journal322 (7289): 757–63. ISSN 0959-8138. PMC 30550. PMID 11282859.

[23] Hu FB, Stampfer MJ (November 1999). "Nut consumption and risk of coronary heart disease: a review of epidemiologic evidence". CurrentAtherosclerosis Reports 1 (3): 204–209. doi:10.1007/s11883-999-0033-7. PMID 11122711.

[24] Truswell, A. Stewart (February 1994). "Review of dietary intervention studies: effect on coronary events and on total mortality". Australianand New Zealand Journal of Medicine 24 (1): 98–106. doi:10.1111/j.1445-5994.1994.tb04444.x. PMID 8002875.

[25] Astrup A, Dyerberg J, Elwood P, et al. (April 2011). "The role of reducing intakes of saturated fat in the prevention of cardiovasculardisease: where does the evidence stand in 2010?". Am. J. Clin. Nutr. 93 (4): 684–8. doi:10.3945/ajcn.110.004622. PMID 21270379.

[26] Jebb SA, Lovegrove JA, Griffin BA, et al. (October 2010). "Effect of changing the amount and type of fat and carbohydrate on insulinsensitivity and cardiovascular risk: the RISCK (Reading, Imperial, Surrey, Cambridge, and Kings) trial". Am. J. Clin. Nutr. 92 (4): 748–58.doi:10.3945/ajcn.2009.29096. PMID 20739418.

[27] Faculty of Public Health of the Royal Colleges of Physicians of the United Kingdom. Position Statement on Fat (http:/ / www. fph. org. uk/uploads/ ps_fat. pdf) [cited 2011-01-25].

[28] Report of a Joint WHO/FAO Expert Consultation (2003). "Diet, Nutrition and the Prevention of Chronic Diseases" (http:/ / www. who. int/hpr/ NPH/ docs/ who_fao_expert_report. pdf). World Health Organization. . Retrieved 2011-03-11.

[29] "Cholesterol" (http:/ / www. irishheart. ie/ iopen24/ cholesterol-t-7_20_87. html). Irish Heart Foundation. . Retrieved 2011-02-28.[30] U.S. Department of Agriculture and U.S. Department of Health and Human Services. (December 2010). Dietary Guidelines for Americans,

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[34] Clarke, R; Frost, C; Collins, R; Appleby, P; Peto, R (1997). "Dietary lipids and blood cholesterol: quantitative meta-analysis of metabolicward studies". BMJ (Clinical research ed.) 314 (7074): 112–7. PMC 2125600. PMID 9006469.

[35] Bucher, HC; Griffith, LE; Guyatt, GH (February 1999). "Systematic review on the risk and benefit of different cholesterol-loweringinterventions" (http:/ / atvb. ahajournals. org/ cgi/ content/ full/ 19/ 2/ 187). Arteriosclerosis Thrombosis and Vascular Biology 19 (2):187–195. PMID 9974397. .

[36] Lewington S, Whitlock G, Clarke R, Sherliker P, Emberson J, Halsey J, Qizilbash N, Peto R, Collins R (December 2007). "Bloodcholesterol and vascular mortality by age, sex, and blood pressure: a meta-analysis of individual data from 61 prospective studies with 55,000vascular deaths". Lancet 370 (9602): 1829–39. doi:10.1016/S0140-6736(07)61778-4. PMID 18061058.

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[37] Labarthe, Darwin (2011). "Chapter 11 Adverse Blood Lipid Profile". Epidemiology and prevention of cardiovascular disease: a globalchallenge (2 ed.). Jones and Bartlett Publishers. p. 290. ISBN 978-0-7637-4689-6.

[38] Labarthe, Darwin (2011). "Chapter 11 Adverse Blood Lipid Profile". Epidemiology and prevention of cardiovascular disease: a globalchallenge (2 ed.). Jones and Bartlett Publishers. p. 277. ISBN 978-0-7637-4689-6.

[39] Thijssen, MA; Mensink RP (2005). "Fatty Acids and Atherosclerotic Risk". In von Eckardstein A. Atherosclerosis: Diet and Drugs.Springer Science+Business Media. pp.  171–2 (http:/ / books. google. com/ books?id=kvo6BN1AGNAC& pg=PA171& dq=#v=onepage& q&f=false). ISBN 978-3-540-22569-0.

[40] Boyd NF, Stone J, Vogt KN, Connelly BS, Martin LJ, Minkin S (November 2003). "Dietary fat and breast cancer risk revisited: ameta-analysis of the published literature". British Journal of Cancer 62 (9): 1672–1685. doi:10.1038/sj.bjc.6601314. PMC 2394401.PMID 14583769.

[41] Hanf V, Gonder U (2005-12-01). "Nutrition and primary prevention of breast cancer: foods, nutrients and breast cancer risk.". Europeanjournal of obstetrics, gynecology, and reproductive biology 123 (2): 139–149. doi:10.1016/j.ejogrb.2005.05.011. PMID 16316809.

[42] Lof M, Weiderpass E (2009 Feb). "Impact of diet on breast cancer risk.". Current opinion in obstetrics & gynecology 21 (1): 80–85.doi:10.1097/GCO.0b013e32831d7f22. PMID 19125007.

[43] Freedman LS, Kipnis V, Schatzkin A, Potischman N (2008 Mar-Apr). "Methods of Epidemiology: Evaluating the Fat–Breast CancerHypothesis – Comparing Dietary Instruments and Other Developments". Cancer journal (Sudbury, Mass.) 14 (2): 69–74.doi:10.1097/PPO.0b013e31816a5e02. PMC 2496993. PMID 18391610.

[44] "4- Food and Drinks" (http:/ / www. dietandcancerreport. org/ downloads/ chapters/ chapter_04. pdf) (pdf). Food, Nutrition, PhysicalActivity, and the Prevention of Cancer: a Global Perspective. World Cancer Research Fund. 2007. pp. 139. ISBN 978-0-9722522-2-5. .Retrieved 2011-09-01.

[45] Huncharek M, Kupelnick B (2001). "Dietary fat intake and risk of epithelial ovarian cancer: a meta-analysis of 6,689 subjects from 8observational studies". Nutrition and Cancer 40 (2): 87–91. doi:10.1207/S15327914NC402_2. PMID 11962260.

[46] Männistö S, Pietinen P, Virtanen MJ, et al. (December 2003). "Fatty acids and risk of prostate cancer in a nested case-control study in malesmokers" (http:/ / cebp. aacrjournals. org/ cgi/ pmidlookup?view=long& pmid=14693732). Cancer Epidemiology, Biomarkers & Prevention12 (12): 1422–8. PMID 14693732. .

[47] Crowe FL, Allen NE, Appleby PN, et al. (November 2008). "Fatty acid composition of plasma phospholipids and risk of prostate cancer in acase-control analysis nested within the European Prospective Investigation into Cancer and Nutrition" (http:/ / www. ajcn. org/ cgi/pmidlookup?view=long& pmid=18996872). The American Journal of Clinical Nutrition 88 (5): 1353–63. PMID 18996872. .

[48] Kurahashi N, Inoue M, Iwasaki M, Sasazuki S, Tsugane AS (April 2008). "Dairy product, saturated fatty acid, and calcium intake andprostate cancer in a prospective cohort of Japanese men". Cancer Epidemiology, Biomarkers & Prevention 17 (4): 930–7.doi:10.1158/1055-9965.EPI-07-2681. PMID 18398033.

[49] Corwin, R. L.; Hartman, T. J.; MacZuga, S. A.; Graubard, B. I. (2006). "Dietary saturated fat intake is inversely associated with bonedensity in humans: Analysis of NHANES III". The Journal of nutrition 136 (1): 159–165. PMID 16365076.

[50] "Saturated and Trans Fats" (http:/ / www. hc-sc. gc. ca/ fn-an/ label-etiquet/ nutrition/ cons/ fats-sat-trans-graisses-eng. php). . Retrieved2010-12-21.

[51] "Dietary Guidelines for Americans 2005" (http:/ / www. health. gov/ dietaryguidelines/ dga2005/ document/ html/ chapter6. htm). .Retrieved 2010-12-21.

[52] "Saturated Fat" (http:/ / www. eatwell. gov. uk/ healthydiet/ fss/ fats/ satfat/ ). . Retrieved 2010-12-02.1[53] "Australian Dietary Guidelines and the Australian Guide to Healthy Eating" (http:/ / www. health. gov. au/ internet/ healthyactive/

publishing. nsf/ Content/ eating). . Retrieved 2010-12-21.[54] "Getting the Fats Right!" (http:/ / www. hpb. gov. sg/ foodforhealth/ article. aspx?id=5634). . Retrieved 2010-12-21.[55] "Citizens Health Knowledge Centre Nutrition" (http:/ / india. gov. in/ citizen/ health/ nutrition_new. php). . Retrieved 2010-12-21.[56] "New Zealand Food and Nutrition Guideline Statements for Healthy Adults" (http:/ / www. moh. govt. nz/ moh. nsf/ indexmh/

nutrition-foodandnutritionguidelinestatements). . Retrieved 2010-12-21.[57] "Food and Drugs Board Regulating for Your Safety Eating Healthy" (http:/ / www. fdbghana. gov. gh/ ). . Retrieved 2010-12-21.[58] "Hypertension (High Blood Pressure)" (http:/ / www. health. gov. gy/ hi_hypertension. php). . Retrieved 2010-12-21.[59] "Nutrition Labelling" (http:/ / www. cfs. gov. hk/ english/ faq/ faq_14. html). . Retrieved 2010-12-21.[60] "Trends in Intake of Energy, Protein, Carbohydrate, Fat, and Saturated Fat — United States, 1971–2000" (http:/ / www. cdc. gov/ od/ oc/

media/ mmwrnews/ n040206. htm#mmwr2). Centers for Disease Control. 2004. .[61] Lichtenstein AH, Appel LJ, Brands M, et al. (July 2006). "Diet and lifestyle recommendations revision 2006: a scientific statement from the

American Heart Association Nutrition Committee". Circulation 114 (1): 82–96. doi:10.1161/CIRCULATIONAHA.106.176158.PMID 16785338.

[62] Smith SC, Jackson R, Pearson TA, et al. (June 2004). "Principles for national and regional guidelines on cardiovascular disease prevention:a scientific statement from the World Heart and Stroke Forum". Circulation 109 (25): 3112–21. doi:10.1161/01.CIR.0000133427.35111.67.PMID 15226228.

[63] "Dietary Guidelines for Americans" (http:/ / www. fda. gov/ ohrms/ dockets/ dockets/ 06q0458/ 06q-0458-sup0001-02. pdf) (pdf). UnitedStates Department of Agriculture. 2005. .

[64] Joint WHO/FAO Expert Consultation (2003). docs/who_fao_expert_report.pdf "Diet, Nutrition and the Prevention of Chronic Diseases (WHO technical report series 916)" (http:/ / www. who. int/ hpr/ NPH). World Health Organization. pp. 81–94. ISBN 92-4-120916-X.

Saturated fat 39

docs/who_fao_expert_report.pdf. Retrieved 2011-03-11.[65] German, J Bruce; Dillard, Cora J (September 2004). "Saturated fats: what dietary intake?" (http:/ / www. ajcn. org/ content/ 80/ 3/ 550. full).

American Journal of Clinical Nutrition 80 (3): 550–559. PMID 15321792. . Retrieved 2010-12-27.[66] Zelman, K. (2011). "The Great Fat Debate: A Closer Look at the Controversy—Questioning the Validity of Age-Old Dietary Guidance".

Journal of the American Dietetic Association 111 (5): 655–658. doi:10.1016/j.jada.2011.03.026. PMID 21515106.

Further reading• Feinman Richard D (2010). "Saturated Fat and Health: Recent Advances in Research" (http:/ / www. springerlink.

com/ content/ 2h371828pu7tju44/ ). Lipids 45 (10): 891–892. doi:10.1007/s11745-010-3446-8. PMID 20827513.• Howard BV, Van Horn L, Hsia J, Manson JE, Stefanick ML, Wassertheil-Smoller S, Kuller LH, LaCroix AZ,

Langer RD, Lasser NL, et al. (February 8, 2006). Low-fat dietary pattern and risk of cardiovascular disease: theWomen's Health Initiative Randomized Controlled Dietary Modification Trial (http:/ / jama. ama-assn. org/content/ 295/ 6/ 655. full). Journal of the American Medical Association 295 (6): 655-66. doi:10.1001/jama.295.6.655. PubMed 16467234.

• Zelman Kathleen, Willett Walter C., Kuller Lewis H., Mozaffarian Dariush, Lichtenstein Alice H. (2011). "TheGreat Fat Debate" (http:/ / www. adajournal. org/ issues?issue_key=S0002-8223(11)X0005-6). Journal of theAmerican Dietetic Association 111 (5): 655–677. doi:10.1016/j.jada.2011.03.026. PMID 21515106.

Unsaturated fatAn unsaturated fat is a fat or fatty acid in which there is at least one double bond within the fatty acid chain. A fatmolecule is monounsaturated if it contains one double bond, and polyunsaturated if it contains more than one doublebond. Where double bonds are formed, hydrogen atoms are eliminated. Thus, a saturated fat has no double bonds,has the maximum number of hydrogens bonded to the carbons, and therefore is "saturated" with hydrogen atoms. Incellular metabolism, unsaturated fat molecules contain somewhat less energy (i.e., fewer calories) than an equivalentamount of saturated fat. The greater the degree of unsaturation in a fatty acid (i.e., the more double bonds in the fattyacid) the more vulnerable it is to lipid peroxidation (rancidity). Antioxidants can protect unsaturated fat from lipidperoxidation.

Chemistry and nutrition

Amounts of fat types in selected foods

Double bonds may be in either a cis or a trans isomer, depending onthe geometry of the double bond. In the cis conformation, hydrogenatoms are on the same side of the double bond, whereas, in the transconformation, they are on opposite sides (see also Trans fat). Saturatedfats are popular with manufacturers of processed foods because theyare less vulnerable to rancidity and are, in general, more solid at roomtemperature than unsaturated fats. Unsaturated chains have a lowermelting point, hence increasing fluidity of the cell membranes.

Although both monounsaturated and polyunsaturated fats can replacesaturated fat in the diet, trans unsaturated fats should be avoided.Replacing saturated fats with unsaturated fats helps to lower levels oftotal cholesterol and LDL cholesterol in the blood.[1] Trans unsaturatedfats are particularly risky because the double bond stereochemistry allows the fat molecules to assume a linearconformation, which leads to efficient packing (i.e., plaque formation). The geometry of the cis double bond

Unsaturated fat 40

introduces a bend in the molecule, thereby precluding stable formations (see specific fatty acid links above fordrawings that illustrate this). Natural sources of fatty acids (see above) are rich in the cis isomer.Although polyunsaturated fats are protective against cardiac arrhythmias, a study of post-menopauseal women with arelatively low fat intake showed that polyunsaturated fat is positively associated with progression of coronaryatherosclerosis, whereas monounsaturated fat is not.[2] This probably is an indication of the greater vulnerability ofpolyunsaturated fats to lipid peroxidation, against which vitamin E has been shown to be protective.[3]

Examples of unsaturated fats are palmitoleic acid, oleic acid, myristoleic acid, linoleic acid, and arachidonic acid.Foods containing unsaturated fats include avocado, nuts, and vegetable oils such as canola and olive oils. Meatproducts contain both saturated and unsaturated fats.Although unsaturated fats are conventionally regarded as 'healthier' than saturated fats,[4] the United States Food andDrug Administration (FDA) recommendation stated that the amount of unsaturated fat consumed should not exceed30% of one's daily caloric intake (or 67 grams given a 2000 Calorie diet). The new dietary guidelines haveeliminated this recommendation at the request of the meat and dairy industries. Most foods contain both unsaturatedand saturated fats. Marketers advertise only one or the other, depending on which one makes up the majority. Thus,various unsaturated fat vegetable oils, such as olive oils, also contain saturated fat).[5]

Role of dietary fats in insulin resistanceIncidence of Insulin resistance is lowered with diets higher in monounsaturated fats (especially oleic acid), while theopposite is true for diets high in polyunsaturated fats (especially large amounts of arachidonic acid) as well assaturated fats (such as arachidic acid), these ratios can be indexed in the phospholipids of human skeletal muscle andin other issues as well. This relationship between dietary fats and insulin resistance is presumed secondary to therelationship between insulin resistance and inflammation, which is partially modulated by dietary fat ratios(Omega3/6/9) with both omega 3 and 9 thought to be anti-inflammatory, and omega 6 pro-inflammatory (as well asby numerous other dietary components, particularly polyphenols, and by exercise as well, with both of theseanti-inflammatory). Although both pro-inflammatory and anti-inflammatory types of fat are biologically necessary,fat dietary ratios in most US diets are skewed towards Omega 6, with subsequent disinhibition of inflammation andpotentiation of insulin resistance [6]

Membrane composition as a metabolic enablerCell membranes of mammals have a higher composition of polyunsaturated fat (DHA, omega-3 fatty acid) and alower composition of monounsaturated fat than do reptiles. Higher polyunsaturated membrane content gives greatermembrane fluidity (and functionality), commensurate with the higher metabolic rate of the warm-blooded species. Infish, however, increasingly cold environments lead to increasingly high cell membrane content of bothmonounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and functionality) at thelower temperatures.[7]

Unsaturated fat 41

References[1] Reiner Željko et. al. (28 June 2011). "ESC/EAS Guidelines for the management of dyslipidaemias: the Task Force for the management of

dyslipidaemias of the European Society of Cardiology (ESC) and the European Atherosclerosis Society (EAS)" (http:/ / eurheartj.oxfordjournals. org/ content/ 32/ 14/ 1769. long). European Heart Journal 32 (14): 1769–1818. .

[2] Dariush Mozaffarian; Rimm, EB; Herrington, DM (1 November 2004). "Dietary fats, carbohydrate, and progression of coronaryatherosclerosis in postmenopausal women" (http:/ / www. ajcn. org/ cgi/ content/ full/ 80/ 5/ 1175). American Journal of Clinical Nutrition 80(5): 1175–1184. PMC 1270002. PMID 15531663. .

[3] B Leibovitz; Hu, ML; Tappel, AL (1990). "Dietary supplements of vitamin E, beta-carotene, coenzyme Q10 and selenium protect tissuesagainst lipid peroxidation in rat tissue slices". The Journal of Nutrition 120 (1): 97–104. PMID 2303916.

[4] BBC Health (http:/ / www. bbc. co. uk/ health/ healthy_living/ nutrition/ basics_fatsugar. shtml), retrieved June 6, 2007.][5] LH Storlien; Baur, LA; Kriketos, AD; Pan, DA; Cooney, GJ; Jenkins, AB; Calvert, GD; Campbell, LV (1996). "Dietary fats and insulin

action". Diabetologica 39 (6): 621–631. doi:10.1007/BF00418533. PMID 8781757.[6] LH Storlien; Baur, LA; Kriketos, AD; Pan, DA; Cooney, GJ; Jenkins, AB; Calvert, GD; Campbell, LV (1996). "Dietary fats and insulin

action". Diabetologica 39 (6): 621–631. doi:10.1007/BF00418533. PMID 8781757.[7] AJ Hulbert (2003). "Life, death and membrane bilayers" (http:/ / jeb. biologists. org/ cgi/ content/ full/ 206/ 14/ 2303). The Journal of

Experimental Biology 206 (Pt 14): 2303–2311. doi:10.1242/jeb.00399. PMID 12796449. .

Monounsaturated fatIn biochemistry and nutrition, monounsaturated fats or MUFA (MonoUnsaturated Fatty Acid) are fatty acids thathave one double bond in the fatty acid chain and all of the remainder of the carbon atoms in the chain aresingle-bonded. By contrast, polyunsaturated fatty acids have more than one double bond.Fatty acids are long-chained molecules having an alkyl group at one end and a carboxylic acid group at the otherend. Fatty acid viscosity (thickness) and melting temperature increases with decreasing number of double bonds.Therefore, monounsaturated fatty acids have a higher melting point than polyunsaturated fatty acids (more doublebonds) and a lower melting point than saturated fatty acids (no double bonds). Monounsaturated fatty acids areliquids at room temperature and semisolid or solid when refrigerated. And if are taken to vacuum, they are destroyed.

Molecular description of oleic acidsCommon monounsaturated fatty acids are palmitoleic acid (16:1 n−7), cis-vaccenic acid (18:1 n−7) and oleic acid(18:1 n−9). Palmitoleic acid has 16 carbon atoms with the first double bond occurring 7 carbon atoms away from themethyl group (and 9 carbons from the carboxyl end). It can be lengthened to the 18-carbon cis-vaccenic acid. Oleicacid has 18 carbon atoms with the first double bond occurring 9 carbon atoms away from the carboxylic acid group.The illustrations below show a molecule of oleic acid in Lewis formula and as a space-filling model.

Relation to healthAlthough polyunsaturated fats protect against cardiovascular disease by providing more membrane fluidity thanmonounsaturated fats, they are more vulnerable to lipid peroxidation (rancidity). On the other hand, somemonounsaturated fatty acids (in the same way as saturated fats) may promote insulin resistance, whereaspolyunsaturated fatty acids may be protective against insulin resistance.[1][2] Furthermore, the large scale KANWUstudy found that increasing monounsaturated fat and decreasing saturated fat intake could improve insulinsensitivity, but only when the overall fat intake of the diet was low.[3]

Monounsaturated fat 42

Foods containing monounsaturated fats reduce low-density lipoprotein (LDL) cholesterol, while possibly increasinghigh-density lipoprotein (HDL) cholesterol.[4] However, their true ability to raise HDL is still in debate.Levels of oleic and monounsaturated fatty acids in red blood cell membranes were positively associated with breastcancer risk. The saturation index (SI) of the same membranes was inversely associated with breast cancer risk.Monounsaturated fats and low SI in erythrocyte membranes are predictors of postmenopausal breast cancer. Both ofthese variables depend on the activity of the enzyme 9-d delta 9 desaturase.[5]

In children, consumption of monounsaturated oils is associated with healthier serum lipid profiles.[6]

Natural sourcesMonounsaturated fats are found in natural foods such as red meat, whole milk products, nuts and high fat fruits suchas olives and avocados. Olive oil is about 75% monounsaturated fat. Canola oil and Cashews are both about 58%monounsaturated fat. Tallow (beef fat) is about 50% monounsaturated fat and lard is about 40% monounsaturatedfat. Other sources include macadamia nut oil, grapeseed oil, groundnut oil (peanut oil), sesame oil, corn oil, popcorn,whole grain wheat, cereal, oatmeal, safflower oil, almond oil, sunflower oil, tea-oil Camellia, and avocado oil.

References[1] Lovejoy, JC (2002). "The influence of dietary fat on insulin resistance". Current Diabetes Reports 2 (5): 435–40.

doi:10.1007/s11892-002-0098-y. PMID 12643169.[2] Satoshi Fukuchi; Hamaguchi, K; Seike, M; Himeno, K; Sakata, T; Yoshimatsu, H (June 1, 2004). "Role of Fatty Acid Composition in the

Development of Metabolic Disorders in Sucrose-Induced Obese Rats" (http:/ / www. ebmonline. org/ cgi/ content/ full/ 229/ 6/ 486).Experimental Biology and Medicine 229 (6): 486–93. PMID 15169967. .

[3] Vessby B, Unsitupa M, Hermansen K, Riccardi G, Rivellese AA, Tapsell LC, Nälsén C, Berglund L, Louheranta A, Rasmussen BM, CalvertGD, Maffetone A, Pedersen E, Gustafsson IB, Storlien LH (2001). "Substituting dietary saturated for monounsaturated fat impairs insulinsensitivity in healthy men and women: The KANWU Study" (http:/ / link. springer-ny. com/ link/ service/ journals/ 00125/ bibs/ 1044003/10440312. htm). Diabetologia 44 (3): 312–9. doi:10.1007/s001250051620. PMID 11317662. .

[4] "You Can Control Your Cholesterol: A Guide to Low-Cholesterol Living" (http:/ / www. mercksource. com/ pp/ us/ cns/cns_krames_template. jspzQzpgzEzzSzppdocszSzuszSzcnszSzcontentzSzkrameszSz1292_01zPzhtm). Merck & Co. Inc.. . Retrieved2009-03-14.

[5] Valeria Pala, Vittorio Krogh, Paola Muti, Véronique Chajès, Elio Riboli, Andrea Micheli, Mitra Saadatian, Sabina Sieri, Franco Berrino (July18, 2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study" (http:/ / jnci. oxfordjournals. org/cgi/ content/ full/ 93/ 14/ 1088). JNCL 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870. . Retrieved 2008-11-30.

[6] Sanchez-Bayle M, Gonzalez-Requejo A, Pelaez MJ, Morales MT, Asensio-Anton J, Anton-Pacheco E (2008). "A cross-sectional study ofdietary habits and lipid profiles. The Rivas-Vaciamadrid study". Eur. J. Pediatr. 167 (2): 149–54. doi:10.1007/s00431-007-0439-6.PMID 17333272.

External links• Fats (Mayo Clinic) (http:/ / www. mayoclinic. com/ health/ diabetes-diet/ DA00075)• Types of Fats (Cardiovascular Consultants) (http:/ / www. heartmaine. com/ resources/ types-of-fats)• The Chemistry of Unsaturated Fats (http:/ / www. benbest. com/ health/ essfat. html#chem)

Polyunsaturated fat 43

Polyunsaturated fatPolyunsaturated lipids are triacylglycerols in which the hydrocarbon tails (caudae) of this ester constitutespolyunsaturated fatty acid (PUFA) (fatty acids possessing more than a single carbon–carbon double bond).[1][2]

"Unsaturated" refers to the fact that the molecules contain less than the maximum amount of hydrogen. Thesematerials exist as cis or trans isomers depending on the geometry of the double bond.Saturated fats have hydrocarbon chains which can be most readily aligned. The hydrocarbon chains in trans fatsalign more readily than those in cis fats, but less well than those in saturated fats. This means that, in general, themelting points of fats increase from cis to trans unsaturated and then to saturated. See the section on chemicalstructure of fats for more information.

Chemical structure of the polyunsaturated fat linoleic acid.

3D representation of linoleic acid in a bent conformation.

The position of the carbon-carbon doublebonds in carboxylic acid chains in fats isdesignated by Greek letters. The carbonatom closest to the carboxyl group is thealpha carbon, the next carbon is the betacarbon and so on. In fatty acids the carbonatom of the methyl group at the end of thehydrocarbon chain is called the omegacarbon because omega is the last letter of theGreek alphabet. Omega-3 fatty acids have adouble bond three carbons away from themethyl carbon, whereas omega-6 fatty acidshave a double bond six carbons away fromthe methyl carbon. The illustration belowshows the omega-6 fatty acid, linoleic acid.

While the nutritional aspects ofpolyunsaturated fats are of highest concern,these materials do have non-foodapplications. Drying oils, which polymerizeon exposure to oxygen to form solid films,are polyunsaturated fats. The most commonones are linseed (flax seed) oil, tung oil,poppy seed oil, perilla oil, and walnut oil. These oils are used to make paints and varnishes.

Dietary Sources

Polyunsaturated fat can be found mostly in nuts, seeds, fish, algae, leafy greens, and krill. Whole food sources arealways best, as processing and heating may damage polyunsaturated fats.

Polyunsaturated fat 44

Health

BenefitsOmega-3 fatty acids in algal oil, fish oil, fish and seafood have been shown to lower the risk of heart attacks.[3]

Omega-6 fatty acids in sunflower oil and safflower oil may also reduce the risk of cardiovascular disease.[4]

Among n-3 fatty acids [Omega-3], neither long-chain nor short-chain forms were consistently associated with breastcancer risk. High levels of docosahexaenoic acid (DHA), however, the most abundant n-3 PUFA [Omega-3] inerythrocyte (red blood cell) membranes, were associated with a reduced risk of breast cancer.[5] The DHA obtainedthrough the consumption of polyunsaturated fatty acids is positively associated with cognitive and behavioralperformance.[6] In addition DHA is vital for the grey matter structure of the human brain, as well as retinalstimulation and neurotransmission.[7]

Dietary intake of polyunsaturated fatty acids has been shown in several studies to decrease the risk of developingamyotrophic lateral sclerosis (ALS, a.k.a. Lou Gehrig's Disease).[8][9] Essential fatty acids (EFA) are shown todecrease the risk of depression, hypertension, and attention deficit hyperactivity disorder.[10]

There are conflicting associations between dietary factors and incident atrial fibrillation (AF). A 2010 studypublished in AJCN suggested that polyunsaturated fats were found to have no significant association with AF.[11]

The importance of the ratio of omega-6/omega-3 essential fatty acids as established by comparative studies shows anOmega-6:Omega-3 ratio under 4:1 is contributive to health. [12]

Consumption during pregnancyConsumption of omega-3 fatty acids during pregnancy is critical to fetal development. They are required during theprenatal period for the formation of synapses and cell membranes. These processes are also essential in postnatalhuman development for injury response of the central nervous system and retinal stimulation.[10]

A study published in The Journal of Nutrition in 2007 found that the maternal diet of rats affects the brain DHAstatus of offspring. It suggests that a maternal diet containing insufficient amounts of omega-3 polyunsaturated fattyacid can lead to greater risk of decreased accretion of brain DHA in offspring.[13]

Relation to cancerA 2010 study of 3,081 women suffering from breast cancer was done to research the effects of polyunsaturated fatson breast cancer. It demonstrated that the consumption of high amounts of long chain omega-3 polyunsaturated fatsfrom food produced a 25% reduced risk of additional breast cancer events. These women were also shown to havereduced risk of “all-cause mortality.” Consumption of polyunsaturated fats through fish oil supplements was notshown to decrease risk of recurring breast cancer events, although the authors noted that consumption ofsupplements among the group was low, less than 5%.[14]

At least one study in mice has shown that consuming high amounts of polyunsaturated fat (but not monounsaturated fat) may increase the risk of metastasis in cancer patients.[15] The researchers found that linoleic acid in polyunsaturated fats produced increasing membrane phase separation, and thereby increased adherence of circulating tumor cells to blood vessel walls and remote organs. According to the report 'The new findings support earlier evidence from other research that consuming high amounts of polyunsaturated fat may increase the risk of cancer spreading'. The propensity for polyunsaturated fats to oxidize is another possible risk factor.[16][17] This leads to the generation of free radicals and eventually to rancidity. Studies have shown that low dosages of Coenzyme Q10 reduce this oxidation, and a combination of a diet rich in polyunsaturated fatty acids and Coenzyme Q10 supplementation leads to a longer lifespan in rats.[18] Studies on animals have shown a link between polyunsaturated fat and the incidence of tumours. In some of these studies the incidence of tumours increased with increasing intake of polyunsaturated fat, up to about 5% of total energy, near to the middle of the current dietary intake in humans. It is

Polyunsaturated fat 45

advised that the level of polyunsaturated fats in the diet be regulated if Coenzyme Q10 supplements are not beingtaken. However, even without Coenzyme Q10 supplementation, the effect on health might be considered by some tobe more beneficial than harmful, due to the supposed cholesterol lowering effects of unsaturated fats compared tosaturated fats; however, (a) monounsaturated fats have also been posited to lead to lower cholesterol levels; and (b) itis no longer clear that saturated fats actually cause elevated blood cholesterol levels.[19]

Food sources of polyunsaturated fat[20]

Food source (100g) Polyunsaturated fat (g)

Walnuts 47

Sunflower Seeds 33

Sesame Seeds 26

Chia Seeds 23.7

Unsalted Peanuts 16

Peanut Butter 14.2

Olive Oil 11

Seaweed 11

Sardines 5

Soybeans 5

Tuna 3

Wild Salmon 2.5

Whole Grain Wheat 0.8

References[1] Ordman, R. (2011). "Introduction to fats. Unpublished manuscript" (http:/ / chemistry. beloit. edu/ Ordman/ nutrition/ essays/ essayfats. htm).

Beloit, WI: Biochemistry Program, Beloit College. .[2] Wyn Snow (30 April 2004). "Chemical and Physical Structure of Fatty Acids" (http:/ / www. supplementquality. com/ news/

fatty_acid_structure. html). . Retrieved 2 May 2012.[3] National Institute of Health (August 1, 2005). "Omega-3 fatty acids, fish oil, alpha-linolenic acid" (http:/ / web. archive. org/ web/

20060503222604/ http:/ / www. nlm. nih. gov/ medlineplus/ print/ druginfo/ natural/ patient-fishoil. html). Archived from the original (http:/ /www. nlm. nih. gov/ medlineplus/ print/ druginfo/ natural/ patient-fishoil. html) on 3 May 2006. . Retrieved 26 March 2006.

[4] Willett, Walter C (September 2007). "The role of dietary n-6 fatty acids in the prevention of cardiovascular disease". Journal ofCardiovascular Medicine 8: S42–5. doi:10.2459/01.JCM.0000289275.72556.13. PMID 17876199.

[5] Pala, V.; Krogh, V; Muti, P; Chajès, V; Riboli, E; Micheli, A; Saadatian, M; Sieri, S et al. (July 2001). "Erythrocyte membrane fatty acidsand subsequent breast cancer: a prospective Italian study". Journal of the National Cancer Institute 93 (14): 1088–95.doi:10.1093/jnci/93.14.1088. PMID 11459870.

[6] Van De Rest, O.; Geleijnse, J. M.; Kok, F. J.; Van Staveren, W. A.; Dullemeijer, C.; Olderikkert, M.G.M.; Beekman, A. T.F.; De Groot, C.P.G.M. (August 2008). "Effects of Fish Oil on cognitive performance in older subjects". Neurology 71 (6): 430–38.doi:10.1212/01.wnl.0000324268.45138.86. PMID 18678826.

[7] Bain, S. (2010). "Achieving optimal omega-3 atty actid status in the vegan population" (http:/ / chemistry. beloit. edu/ Ordman/ posters/posttexts/ prefa07/ bain06. jpg). Beloit, WI: Biochemistry Program. .

[8] Veldink, J H; Kalmijn, S; Groeneveld, G-J; Wunderink, W; Koster, A; De Vries, J H M; Van Der Luyt, J; Wokke, J H J et al. (April 2007)."Intake of polyunsaturated fatty acids and vitamin E reduces the risk of developing amyotrophic lateral sclerosis". Journal of Neurology,Neurosurgery, and Psychiatry 78 (4): 367–71. doi:10.1136/jnnp.2005.083378. PMC 2077791. PMID 16648143.

[9] Okamoto, Kazushi; Kihira, Tameko; Kondo, Tomoyoshi; Kobashi, Gen; Washio, Masakazu; Sasaki, Satoshi; Yokoyama, Tetsuji; Miyake,Yoshihiro et al. (October 2007). "Nutritional status and risk of amyotrophic lateral sclerosis in Japan". Amyotrophic Lateral Sclerosis 8 (5):300–4. doi:10.1080/17482960701472249. PMID 17852010.

Polyunsaturated fat 46

[10] Bain, S. (2010). "Achieving optimal omega-3 fatty acid status in the vegan population" (http:/ / chemistry. beloit. edu/ Ordman/ posters/posttexts/ prefa07/ bain06. jpg). Beloit, WI: Biochemistry Program. .

[11] Shen, J.; Johnson, V. M.; Sullivan, L. M.; Jacques, P. F.; Magnani, J. W.; Lubitz, S. A.; Pandey, S.; Levy, D. et al. (2010). "Dietary factorsand incident atrial fibrillation: The Framingham Heart Study". American Journal of Clinical Nutrition 93 (2): 261–6.doi:10.3945/ajcn.110.001305. PMC 3021424. PMID 21106919.

[12] Simopoulos. "The importance of the ratio of omega-6/omega-3 essential fatty acids" (http:/ / www. ncbi. nlm. nih. gov/ pubmed/ 12442909).The importance of the ratio of omega-6/omega-3 essential fatty acids. National Institutes of Health. . Retrieved 29 January 2012.

[13] Ozias, MK; Carlson, SE; Levant, B (2007). "Maternal Parity and Diet (n-3) Polyunsaturated Fatty Acid Concentration Influence Accretionof Brain Phospholipid Docosahexaenoic Acid in Developing Rats" (http:/ / jn. nutrition. org/ content/ 137/ 1/ 125. abstract). The Journal ofNutrition 137 (1): 125sex–9. PMID 17182812. .

[14] Patterson, R. E.; Flatt, S. W.; Newman, V. A.; Natarajan, L.; Rock, C. L.; Thomson, C. A.; Caan, B. J.; Parker, B. A. et al. (2010). "MarineFatty Acid Intake is Associated with Breast Cancer Prognosis". The Journal of Nutrition 141 (2): 201–206. doi:10.3945/jn.110.128777.PMC 3021439. PMID 21178081.

[15] "New findings measure precise impact of fat on cancer spread" (http:/ / www. eurekalert. org/ pub_releases/ 2009-02/ pu-nfm022509. php).2009. .

[16] Scislowski, Valérie; Bauchart, Dominique; Gruffat, Dominique; Laplaud, Paul-Michel; Durand, Denys (2005). "Effect of dietary n-6 and n-3polyunsaturated fatty acids on peroxidizability of lipoproteins in steers". Lipids 40 (12): 1245–56. doi:10.1007/s11745-005-1492-z.PMID 16477809.

[17] Diniz, Yeda Sant'Ana; Cicogna, Antonio C; Padovani, Carlos R; Santana, Lea S; Faine, Luciane A; Novelli, Ethel L.B (2004). "Diets rich insaturated and polyunsaturated fatty acids: metabolic shifting and cardiac health". Nutrition 20 (2): 230–4. doi:10.1016/j.nut.2003.10.012.PMID 14962692.

[18] Quiles, José L; Ochoa, Julio J; Huertas, Jesús R; Mataix, José (2004). "Coenzyme Q supplementation protects from age-related DNAdouble-strand breaks and increases lifespan in rats fed on a PUFA-rich diet". Exp Gerontol. 39 (2): 189–94. doi:10.1016/j.exger.2003.10.002.PMID 15036411.

[19] Guyenet, Stephen. "does dietary saturated fat increase blood cholesterol?" (http:/ / wholehealthsource. blogspot. com/ 2011/ 01/does-dietary-saturated-fat-increase. html). . Retrieved 13 November 2011.

[20] "National nutrient database for standard reference, release 23" (http:/ / www. nal. usda. gov/ fnic/ foodcomp/ search/ ). United StatesDepartment of Agriculture, Agricultural Research Service. 2011. .

External links• Polyunsaturated Fats And Health (http:/ / evilcyber. com/ nutrition/

disrobing-dogma-polyunsaturated-fat-and-health/ )• The Chemistry of Unsaturated Fats (http:/ / www. benbest. com/ health/ essfat. html#chem)

Trans fat 47

Trans fatTrans fat is the common name for unsaturated fat with trans-isomer (E-isomer) fatty acid(s). Because the termrefers to the configuration of a double carbon-carbon bond, trans fats are sometimes monounsaturated orpolyunsaturated, but never saturated. Trans fats do exist in nature but also occur during the processing ofpolyunsaturated fatty acids in food production.[1]

The consumption of trans fats increases the risk of coronary heart disease[2][3] by raising levels of LDL cholesteroland lowering levels of "good" HDL cholesterol.[4] There is an ongoing debate about a possible differentiationbetween trans fats of natural origin and trans fats of vegetable origin but so far no scientific consensus was found.Two Canadian studies, that received funding by the Alberta Livestock and Meat Agency [5] and the Dairy Farmers ofCanada,[6] have shown that the natural trans fat vaccenic acid, found in beef and dairy products, may have anopposite health effect and could actually be beneficial compared to hydrogenated vegetable shortening, or a mixtureof pork lard and soy fat,[6] e.g. lowering total and LDL cholesterol and triglyceride levels.[7][8][9] In lack ofrecognized evidence and scientific agreement, nutritional authorities consider all trans fats as equally harmful forhealth [10][11][12] and recommend that consumption of trans fats be reduced to trace amounts.[13][14]

Unsaturated fat is a fat molecule containing one or more double bonds between the carbon atoms. Since the carbonsare double-bonded to each other, there are fewer bonds connected to hydrogen, so there are fewer hydrogen atoms,hence the name, 'unsaturated'. Cis and trans are terms that refer to the arrangement of the two hydrogen atomsbonded to the carbon atoms involved in a double bond. In the cis arrangement, the hydrogens are on the same side ofthe double bond. In the trans arrangement, the hydrogens are on opposite sides of the double bond.The process of hydrogenation adds hydrogen atoms to unsaturated fats, eliminating double bonds and making theminto partially or completely saturated fats. However, partial hydrogenation, if it is chemical rather than enzymatic,converts a part of cis-isomers into trans-unsaturated fats instead of hydrogenating them completely. Trans fats alsooccur naturally in a limited number of cases: Vaccenyl and conjugated linoleyl (CLA) containing trans fats occurnaturally in trace amounts in meat and dairy products from ruminants, although the latter also constitutes a cis fat.

Trans fat 48

History

Cover of original Crisco cookbook, 1912

Nobel laureate Paul Sabatier worked in the late 1890s to develop thechemistry of hydrogenation, which enabled the margarine, oilhydrogenation, and synthetic methanol industries.[15] Whereas Sabatierconsidered hydrogenation of only vapors, the German chemistWilhelm Normann showed in 1901 that liquid oils could behydrogenated, and patented the process in 1902.[16][17][18] During theyears 1905 – 1910, Normann built a fat-hardening facility in theHerford company. At the same time, the invention was extended to alarge-scale plant in Warrington, England, at Joseph Crosfield & Sons,Limited. It took only two years until the hardened fat could besuccessfully produced in the plant in Warrington, commencingproduction in the autumn of 1909. The initial year's production totallednearly 3,000 tonnes.[19] In 1909, Procter & Gamble acquired the USrights to the Normann patent;[20] in 1911, they began marketing thefirst hydrogenated shortening, Crisco (composed largely of partiallyhydrogenated cottonseed oil). Further success came from the marketingtechnique of giving away free cookbooks in which every recipe calledfor Crisco.

Normann's hydrogenation process made it possible to stabilizeaffordable whale oil or fish oil for human consumption, a practice kept secret to avoid consumer distaste.[21]

Prior to 1910, dietary fats consisted primarily of butterfat, beef tallow, and lard. During Napoleon’s reign in Francein the early 19th century, a type of margarine was invented to feed the troops using tallow and buttermilk; it did notgain acceptance in the U.S. In the early 20th century, soybeans began to be imported into the U.S. as a source ofprotein; soybean oil was a by-product. What to do with that oil became an issue. At the same time, there was notenough butterfat available for consumers. The method of hydrogenating fat and turning a liquid fat into a solid onehad been discovered, and now the ingredients (soybeans) and the "need" (shortage of butter) were there. Later, themeans for storage, the refrigerator, was a factor in trans fat development. The fat industry found that hydrogenatedfats provided some special features to margarines, which, unlike butter, allowed margarine to be taken out of therefrigerator and immediately spread on a slice of bread. By some minor changes to the chemical composition ofhydrogenated fat, such hydrogenated fat was found to provide superior baking properties compared to lard.Margarine made from hydrogenated soybean oil began to replace butterfat. Hydrogenated fat such as Crisco andSpry, sold in England, began to replace lard in the baking of bread, pies, cookies, and cakes in 1920.[22]

In the 1940s, Dr Catherine Kousmine researched the effects of trans fats on cancer.Production of hydrogenated fats increased steadily until the 1960s, as processed vegetable fats replaced animal fatsin the US and other western countries. At first, the argument was a financial one due to lower costs; advocates alsosaid that the unsaturated trans fats of margarine were healthier than the saturated fats of butter.[23]

As early as 1956 there were suggestions in the scientific literature that trans fats could be a cause of the largeincrease in coronary artery disease but after three decades the concerns were still largely unaddressed.[23][24] Studiesin the early 1990s, however, brought renewed scrutiny and confirmation of the negative health impact of trans fats.In 1994, it was estimated that trans fats caused 20,000 deaths annually in the US from heart disease.[25]

Mandatory food labeling for trans fats was introduced in several countries.[26] Campaigns were launched by activists to bring attention to the issue and change the practices of food manufacturers.[27] In January 2007, faced with the prospect of an outright ban on the sale of their product, Crisco was reformulated to meet the United States Food and Drug Administration definition of "zero grams trans fats per serving" (that is less than one gram per tablespoon, or

Trans fat 49

up to 7% by weight; or less than 0.5 grams per serving size)[28][29][30][31] by boosting the saturation and then dilutingthe resulting solid fat with unsaturated vegetable oils.A University of Guelph research group has found a way to mix oils (such as olive, soybean and canola), water,monoglycerides and fatty acids to form a "cooking fat" that acts the same way as trans and saturated fats.[32][33]

ChemistryIn chemical terms, trans fat refers to a lipid molecule that contains one or more double bonds in trans geometricconfiguration. A double bond may exhibit one of two possible configurations: trans or cis. In trans configuration, thecarbon chain extends from opposite sides of the double bond, rendering a straighter molecule, whereas, in cisconfiguration, the carbon chain extends from the same side of the double bond, rendering a bent molecule.

Trans (Elaidic acid) Cis (Oleic acid) Saturated (Stearic acid)

Elaidic acid is the principal trans unsaturated fattyacid often found in partially hydrogenated vegetable

oils.[34]

Oleic acid is a cis unsaturated fatty acid thatcomprises 55–80% of olive oil.[35]

Stearic acid is a saturated fatty acid found in animalfats and is the intended product in full

hydrogenation. Stearic acid is neither cis nor transbecause it has no double bonds.

These fatty acids are geometric isomers (structurally identical except for the arrangement of the doublebond).

This fatty acid contains no double bond and is notisomeric with the previous two.

Fatty acids are characterized as either saturated or unsaturated based on the presence of double bonds in itsstructure. If the molecule contains no double bonds, it is said to be saturated; otherwise, it is unsaturated to somedegree.[36][37]

Only unsaturated fats can be trans or cis fat, since only a double bond can be locked to these orientations. Saturatedfatty acids are never called trans fats because they have no double bonds, and, therefore, all their bonds are freelyrotatable. Other types of fatty acids such as crepenynic acid, which contains a triple bond, are rare and of nonutritional significance.Carbon atoms are tetravalent, forming four covalent bonds with other atoms, whereas hydrogen atoms bond withonly one other atom. In saturated fatty acids, each carbon atom is connected to its two neighbour carbon atoms aswell as two hydrogen atoms. In unsaturated fatty acids, the carbon atoms that are missing a hydrogen atom are joinedby double bonds rather than single bonds so that each carbon atom participates in four bonds.

Trans fat 50

Wilhelm Normann patentedthe hydrogenation of liquid

oils in 1902

Hydrogenation of an unsaturated fatty acid refers to the addition of hydrogen atoms tothe acid, causing double bonds to become single ones, as carbon atoms acquire newhydrogen partners (to maintain four bonds per carbon atom). Full hydrogenation resultsin a molecule containing the maximum amount of hydrogen (in other words, theconversion of an unsaturated fatty acid into a saturated one). Partial hydrogenationresults in the addition of hydrogen atoms at some of the empty positions, with acorresponding reduction in the number of double bonds. Typical commercialhydrogenation is partial in order to obtain a malleable mixture of fats that is solid atroom temperature, but melts upon baking (or consumption).

In most naturally occurring unsaturated fatty acids, the hydrogen atoms are on the sameside of the double bonds of the carbon chain (cis configuration — from the Latin,meaning "on the same side"). However, partial hydrogenation reconfigures most of thedouble bonds that do not become chemically saturated, twisting them so that thehydrogen atoms end up on different sides of the chain. This type of configuration is called trans, from the Latin,meaning "across".[38] The trans configuration is the lower energy form, and is favored when catalyticallyequilibrated as a side reaction in hydrogenation.

The same molecule, containing the same number of atoms, with a double bond in the same location, can be either atrans or a cis fatty acid depending on the configuration of the double bond. For example, oleic acid and elaidic acidare both unsaturated fatty acids with the chemical formula C9H17C9H17O2.[39] They both have a double bond locatedmidway along the carbon chain. It is the configuration of this bond that sets them apart. The configuration hasimplications for the physical-chemical properties of the molecule. The trans configuration is straighter, while the cisconfiguration is noticeably kinked as can be seen from the three-dimensional representation shown above.The trans fatty acid elaidic acid has different chemical and physical properties, owing to the slightly different bondconfiguration. It has a much higher melting point, 45 °C, than oleic acid, 13.4 °C, due to the ability of the transmolecules to pack more tightly, forming a solid that is more difficult to break apart.[39] This notably means that it is asolid at human body temperatures.In food production, the goal is not to simply change the configuration of double bonds while maintaining the sameratios of hydrogen to carbon. Instead, the goal is to decrease the number of double bonds and increase the amount ofhydrogen in the fatty acid. This changes the consistency of the fatty acid and makes it less prone to rancidity (inwhich free radicals attack double bonds). Production of trans fatty acids is therefore an undesirable side effect ofpartial hydrogenation.Catalytic partial hydrogenation necessarily produces trans-fats, because of the reaction mechanism. In the firstreaction step, one hydrogen is added, with the other, coordinatively unsaturated, carbon being attached to thecatalyst. The second step is the addition of hydrogen to the remaining carbon, producing a saturated fatty acid. Thefirst step is reversible, such that the hydrogen is readsorbed on the catalyst and the double bond is re-formed. Theintermediate with only one hydrogen added contains no double bond and can freely rotate. Thus, the double bondcan re-form as either cis or trans, of which trans is favored, regardless the starting material. Complete hydrogenationalso hydrogenates any produced trans fats to give saturated fats.Researchers at the United States Department of Agriculture have investigated whether hydrogenation can be achieved without the side effect of trans fat production. They varied the pressure under which the chemical reaction was conducted — applying 1400 kPa (200 psi) of pressure to soybean oil in a 2-liter vessel while heating it to between 140 °C and 170 °C. The standard 140 kPa (20 psi) process of hydrogenation produces a product of about 40% trans fatty acid by weight, compared to about 17% using the high-pressure method. Blended with unhydrogenated liquid soybean oil, the high-pressure-processed oil produced margarine containing 5 to 6% trans fat. Based on current U.S. labeling requirements (see below), the manufacturer could claim the product was free of trans

Trans fat 51

fat.[40] The level of trans fat may also be altered by modification of the temperature and the length of time duringhydrogenation.Trans fat levels may be measured. Measurement techniques include chromatography (by silver ion chromatographyon thin layer chromatography plates, or small high-performance liquid chromatography columns of silica gel withbonded phenylsulfonic acid groups whose hydrogen atoms have been exchanged for silver ions). The role of silverlies in its ability to form complexes with unsaturated compounds. Gas chromatography and mid-infraredspectroscopy are other methods in use.

Presence in food

Salers Cow. Milk and meat from cows and otherruminants contains naturally occurring trans fats

in small quantities

A type of trans fat occurs naturally in the milk and body fat ofruminants (such as cattle and sheep) at a level of 2–5% of total fat.[41]

Natural trans fats, which include conjugated linoleic acid (CLA) andvaccenic acid, originate in the rumen of these animals. CLA has twodouble bonds, one in the cis configuration and one in trans, whichmakes it simultaneously a cis- and a trans-fatty acid.

Animal-based fats were once the only trans fats consumed, but by farthe largest amount of trans fat consumed today is created by theprocessed food industry as a side effect of partially hydrogenatingunsaturated plant fats (generally vegetable oils). These partiallyhydrogenated fats have displaced natural solid fats and liquid oils inmany areas, the most notable ones being in the fast food, snack food,

fried food, and baked goods industries. They can only be made by cooking with a very high heat, at temperaturesimpossible in a household kitchen.

Partially hydrogenated oils have been used in food for many reasons. Partial hydrogenation increases product shelflife and decreases refrigeration requirements. Many baked foods require semi-solid fats to suspend solids at roomtemperature; partially hydrogenated oils have the right consistency to replace animal fats such as butter and lard atlower cost. They are also an inexpensive alternative to other semi-solid oils such as palm oil.Partially hydrogenated plant oils, and also non-hydrogenated plant shortenings made from naturally saturated palmoil, coconut oil and palm kernel oil, can be used to replace animal fats in foodstuffs for adherents to the dietary rulesof Kashrut (kosher) and Halal, and for vegetarians and vegans.Up to 45% of the total fat in those foods containing artificial trans fats formed by partially hydrogenating plant fatsmay be trans fat.[41] Baking shortenings, in general, contain 30% trans fats compared to their total fats, whereasanimal fats from ruminants such as butter contain up to 4%. Margarines not reformulated to reduce trans fats maycontain up to 15% trans fat by weight.[42]

It has been established that trans fats in human milk fluctuate with maternal consumption of trans fat, and that theamount of trans fats in the bloodstream of breastfed infants fluctuates with the amounts found in their milk. Reportedpercentages of trans fats (compared to total fats) in human milk range from 1% in Spain, 2% in France, 4% inGermany, and 7% in Canada and the United States.[43]

Trans fats are used in shortenings for deep-frying in restaurants, as they can be used for longer than most conventional oils before becoming rancid. In the early 21st century, non-hydrogenated vegetable oils that have lifespans exceeding that of the frying shortenings became available.[44] As fast-food chains routinely use different fats in different locations, trans fat levels in fast food can have large variations. For example, an analysis of samples of McDonald's French fries collected in 2004 and 2005 found that fries served in New York City contained twice as much trans fat as in Hungary, and 28 times as much as in Denmark (where trans fats are restricted). At KFC, the pattern was reversed with Hungary's product containing twice the trans fat of the New York product. Even within the

Trans fat 52

US there was variation, with fries in New York containing 30% more trans fat than those from Atlanta.[45]

Nutritional guidelinesThe National Academy of Sciences (NAS) advises the United States and Canadian governments on nutritionalscience for use in public policy and product labeling programs. Their 2002 Dietary Reference Intakes for Energy,Carbohydrate, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids[46] contains their findings andrecommendations regarding consumption of trans fat (summary [47]).Their recommendations are based on two key facts. First, "trans fatty acids are not essential and provide no knownbenefit to human health",[2] whether of animal or plant origin.[48] Second, while both saturated and trans fats increaselevels of LDL cholesterol (so-called bad cholesterol), trans fats also lower levels of HDL cholesterol (goodcholesterol);[3] thus increasing the risk of coronary heart disease. The NAS is concerned "that dietary trans fattyacids are more deleterious with respect to coronary heart disease than saturated fatty acids".[3] This analysis issupported by a 2006 New England Journal of Medicine (NEJM) scientific review that states "from a nutritionalstandpoint, the consumption of trans fatty acids results in considerable potential harm but no apparent benefit."[49]

Because of these facts and concerns, the NAS has concluded there is no safe level of trans fat consumption. There isno adequate level, recommended daily amount or tolerable upper limit for trans fats. This is because any incrementalincrease in trans fat intake increases the risk of coronary heart disease.[3]

Despite this concern, the NAS dietary recommendations have not recommended the elimination of trans fat from thediet. This is because trans fat is naturally present in many animal foods in trace quantities, and therefore its removalfrom ordinary diets might introduce undesirable side effects and nutritional imbalances if proper nutritional planningis not undertaken. The NAS has, therefore, "recommended that trans fatty acid consumption be as low as possiblewhile consuming a nutritionally adequate diet".[50] Like the NAS, the World Health Organization has tried to balancepublic health goals with a practical level of trans fat consumption, recommending in 2003 that trans fats be limited toless than 1% of overall energy intake.[41]

The US National Dairy Council has asserted that the trans fats present in animal foods are of a different type thanthose in partially hydrogenated oils, and do not appear to exhibit the same negative effects.[51] While a recentscientific review agrees with the conclusion (stating that "the sum of the current evidence suggests that the Publichealth implications of consuming trans fats from ruminant products are relatively limited"), it cautions that this maybe due to the low consumption of trans fats from animal sources compared to artificial ones.[49]

Health risksPartially hydrogenated vegetable oils have been an increasingly significant part of the human diet for about 100years (in particular, since the later half of the 20th century and where more processed foods are consumed), andsome deleterious effects of trans fat consumption are scientifically accepted, forming the basis of the healthguidelines discussed above.The exact biochemical methods by which trans fats produce specific health problems are a topic of continuingresearch. One theory is that the human lipase enzyme works only on the cis configuration and cannot metabolize atrans fat. A lipase is a water-soluble enzyme that helps digest, transport, and process dietary lipids such astriglycerides, fats, and oils in most – if not all – living organisms. While the mechanisms through which trans fatscontribute to coronary heart disease are fairly well understood, the mechanism for trans fat's effect on diabetes is stillunder investigation. Trans fatty acids may impair the metabolism of long-chain polyunsaturated fatty acids(LCPUFAs),[52] but maternal pregnancy trans fatty acid intake has been inversely associated with LCPUFAs levelsin infants at birth thought to underlie the positive association between breastfeeding and intelligence.

Trans fat 53

Coronary heart diseaseThe primary health risk identified for trans fat consumption is an elevated risk of coronary heart disease (CHD).[53]

A 1994 study estimated that over 30,000 cardiac deaths per year in the United States are attributable to theconsumption of trans fats.[54] By 2006 upper estimates of 100,000 deaths were suggested.[55] A comprehensivereview of studies of trans fats published in 2006 in the New England Journal of Medicine reports a strong andreliable connection between trans fat consumption and CHD, concluding that "On a per-calorie basis, trans fatsappear to increase the risk of CHD more than any other macronutrient, conferring a substantially increased risk atlow levels of consumption (1 to 3% of total energy intake)".[49][56]

The major evidence for the effect of trans fat on CHD comes from the Nurses' Health Study — a cohort study thathas been following 120,000 female nurses since its inception in 1976. In this study, Hu and colleagues analyzed datafrom 900 coronary events from the study's population during 14 years of followup. He determined that a nurse'sCHD risk roughly doubled (relative risk of 1.94, CI: 1.43 to 2.61) for each 2% increase in trans fat caloriesconsumed (instead of carbohydrate calories). By contrast, it takes more than a 15% increase in saturated fat calories(instead of carbohydrate calories) to produce a similar increase in risk. "The replacement of saturated fat or transunsaturated fat by cis (unhydrogenated) unsaturated fats was associated with larger reductions in risk than anisocaloric replacement by carbohydrates."[57] Hu also reports on the benefits of reducing trans fat consumption.Replacing 2% of food energy from trans fat with non-trans unsaturated fats more than halves the risk of CHD (53%).By comparison, replacing a larger 5% of food energy from saturated fat with non-trans unsaturated fats reduces therisk of CHD by 43%.[57]

Another study considered deaths due to CHD, with consumption of trans fats being linked to an increase inmortality, and consumption of polyunsaturated fats being linked to a decrease in mortality.[53][58]

There are two accepted tests that measure an individual's risk for coronary heart disease, both blood tests. The firstconsiders ratios of two types of cholesterol, the other the amount of a cell-signalling cytokine called C-reactiveprotein. The ratio test is more accepted, while the cytokine test may be more powerful but is still being studied.[53]

The effect of trans fat consumption has been documented on each as follows:• Cholesterol ratio: This ratio compares the levels of LDL (so-called "bad" cholesterol) to HDL (so-called "good"

cholesterol). Trans fat behaves like saturated fat by raising the level of LDL, but, unlike saturated fat, it has theadditional effect of decreasing levels of HDL. The net increase in LDL/HDL ratio with trans fat is approximatelydouble that due to saturated fat.[59] (Higher ratios are worse.) One randomized crossover study published in 2003comparing the effect of eating a meal on blood lipids of (relatively) cis and trans fat rich meals showed thatcholesteryl ester transfer (CET) was 28% higher after the trans meal than after the cis meal and that lipoproteinconcentrations were enriched in apolipoprotein(a) after the trans meals.[60]

• C-reactive protein (CRP): A study of over 700 nurses showed that those in the highest quartile of trans fatconsumption had blood levels of CRP that were 73% higher than those in the lowest quartile.[61] on nutritionlables, when it says "trans fat free" it means 0.5 grams or less.

Other health risksThere are suggestions that the negative consequences of trans fat consumption go beyond the cardiovascular risk. Ingeneral, there is much less scientific consensus asserting that eating trans fat specifically increases the risk of otherchronic health problems:• Alzheimer's Disease: A study published in Archives of Neurology in February 2003 suggested that the intake of

both trans fats and saturated fats promote the development of Alzheimer disease,[62] although not confirmed in ananimal model.[63] It has been found that trans fats impaired memory and learning in middle-age rats. The rats'brains of trans-fat eaters had fewer proteins critical to healthy neurological function. Inflammation in and aroundthe hippocampus, the part of the brain responsible for learning and memory. These are the exact types of changesnormally seen at the onset of Alzheimer's, but seen after six weeks, even though the rats were still young.[64]

Trans fat 54

• Cancer: There is no scientific consensus that consumption of trans fats significantly increases cancer risks acrossthe board.[53] The American Cancer Society states that a relationship between trans fats and cancer "has not beendetermined."[65] One study has found a positive connection between trans fat and prostate cancer.[66] However, alarger study found a correlation between trans fats and a significant decrease in high-grade prostate cancer.[67] Anincreased intake of trans fatty acids may raise the risk of breast cancer by 75%, suggest the results from theFrench part of the European Prospective Investigation into Cancer and Nutrition.[68][69]

• Diabetes: There is a growing concern that the risk of type 2 diabetes increases with trans fat consumption.[53]

However, consensus has not been reached.[49] For example, one study found that risk is higher for those in thehighest quartile of trans fat consumption.[70] Another study has found no diabetes risk once other factors such astotal fat intake and BMI were accounted for.[71]

• Obesity: Research indicates that trans fat may increase weight gain and abdominal fat, despite a similar caloricintake.[72] A 6-year experiment revealed that monkeys fed a trans fat diet gained 7.2% of their body weight, ascompared to 1.8% for monkeys on a mono-unsaturated fat diet.[73][74] Although obesity is frequently linked totrans fat in the popular media,[75] this is generally in the context of eating too many calories; there is not a strongscientific consensus connecting trans fat and obesity, although the 6-year experiment did find such a link,concluding that "under controlled feeding conditions, long-term TFA consumption was an independent factor inweight gain. TFAs enhanced intra-abdominal deposition of fat, even in the absence of caloric excess, and wereassociated with insulin resistance, with evidence that there is impaired post-insulin receptor binding signaltransduction."[74]

• Liver Dysfunction: Trans fats are metabolized differently by the liver than other fats and interfere with delta 6desaturase. Delta 6 desaturase is an enzyme involved in converting essential fatty acids to arachidonic acid andprostaglandins, both of which are important to the functioning of cells.[76]

• Infertility in women: One 2007 study found, "Each 2% increase in the intake of energy from trans unsaturatedfats, as opposed to that from carbohydrates, was associated with a 73% greater risk of ovulatory infertility...".[77]

• Major depressive disorder: Spanish researchers analysed the diets of 12,059 people over six years and found thosewho ate the most trans fats had a 48 per cent higher risk of depression than those who did not eat trans fats.[78]

One mechanism may be trans-fats' substitution for docosahexaenoic acid (DHA) levels in the orbitofrontal cortex(OFC). Very high intake of trans-fatty acids (43% of total fat) in mice from 2 to 16 months of age was associatedwith lowered DHA levels in the brain (p=0.001) [79] When the brains of 15 major depressive subjects who hadcommitted suicide were examined post-mortem and compared against 27 age-matched controls, the suicidalbrains were found to have 16% less (male average) to 32% (female average) less DHA in the OFC. The OFC isknown to control reward, reward expectation and empathy, which are all negatively impacted in depressive mooddisorders, as well as regulating the limbic system.[80]

Public response and regulation

InternationalThe international trade in food is standardized in the Codex Alimentarius. Hydrogenated oils and fats come under thescope of Codex Stan 19.[81] Non-dairy fat spreads are covered by Codex Stan 256-2007.[82] In the CodexAlimentarius, trans fat to be labelled as such is defined as the geometrical isomers of monounsaturated andpolyunsaturated fatty acids having non-conjugated [interrupted by at least one methylene group (−CH2−)]carbon-carbon double bonds in the trans configuration. This definition excludes specifically the healthy trans fats(vaccenic acid and conjugated linoleic acid) which are present especially in human milk, dairy products, and beef.

Trans fat 55

ArgentinaSince August 2006 food products should be labelled with the amount of trans fat in them.[83] Since 2010 vegetableoils and fats directly sold to consumers must only contain 2% of trans fat over total fat, and other food must containless than 5% of their total fat.[84]

AustraliaThe Australian federal government has indicated that it wants to pursue actively a policy of reducing trans fats fromfast foods. The former federal assistant health minister, Christopher Pyne, asked fast food outlets to reduce theirtrans fat usage. A draft plan was proposed, with a September 2007 timetable, in order to reduce reliance on trans fatsand saturated fats.[85] Currently, Australia's food labeling laws do not require trans fats to be shown separately fromthe total fat content. However, margarine in Australia has been virtually free of trans fat since 1996.[86]

AustriaTotal ban on trans fats.

BrazilResolution 360 of 23 December 2003 by the Brazilian ministry of health required for the first time in the country thatthe amount of trans fat to be specified in labels of food products. On 31 July 2006 such labelling of trans fat contentsbecame mandatory. In 2007 the ministry established a target to reduce the total amount of trans fat in anyindustrialized food sold in Brazil to a maximum of 2% by the end of 2010.

CanadaIn November 2004, an opposition day motion seeking a ban similar to Denmark's was introduced by Jack Layton ofthe New Democratic Party, and passed through the House of Commons by an overwhelming 193-73 vote.[87] Like allCommons motions, it served as an expression of the views of the House but was not binding on the government andhas no force under the law.Since December 2005, Health Canada has required that food labels list the amount of trans fat in the nutrition factssection for most foods. Products with less than 0.2 grams of trans fat per serving may be labeled as free of transfats.[88] These labelling allowances are not widely known, but as an awareness of them develops, controversy overtruthful labelling is growing. In Canada, trans fat quantities on labels include naturally occurring trans fats fromanimal sources.[89]

In June 2006, a task force co-chaired by Health Canada and the Heart and Stroke Foundation of Canadarecommended a limit of 5% trans fat (of total fat) in all products sold to consumers in Canada (2% for tubmargarines and spreads).[41] The amount was selected such that "most of the industrially produced trans fats wouldbe removed from the Canadian diet, and about half of the remaining trans fat intake would be of naturally occurringtrans fats". This recommendation has been endorsed by the Canadian Restaurant and Foodservices Association[90]

and Food & Consumer Products of Canada has congratulated the task force on the report,[91] although it did notrecommend delaying implementation to 2010 as they had previously advocated.[92]

Ten months after submitting their report the Heart and Stroke Foundation of Canada and Toronto Public Healthissued a plea to the government of Canada: "to act immediately on the task force's recommendations and to eliminateharmful trans fat from Canada's food supply."[93]

On June 20, 2007, the federal government announced its intention to regulate trans fats to the June 2006 standardunless the food industry voluntarily complied with these limits within two years.[94][95]

On January 1, 2008, Calgary became the first city in Canada to ban trans fats from restaurants and fast food chains. Trans fats present in cooking oils may not exceed 2% of the total fat content.[96] However, the replacement of local

Trans fat 56

health regions with the Alberta Health Services Board in 2009 has temporarily eliminated all enforcement of theban.[97]

Effective September 30, 2009, British Columbia became the first province in Canada to mandate the June 2006recommendation in provincially regulated food services establishments.[98][99]

DenmarkDenmark became the first country to introduce laws strictly regulating the sale of many foods containing trans fats inMarch 2003, a move which effectively bans partially hydrogenated oils. The limit is 2% of fats and oils destined forhuman consumption. This restriction is on the ingredients rather than the final products. This regulatory approachhas made Denmark the only country in which it is possible to eat "far less" than 1 g of industrially produced transfats on a daily basis, even with a diet including prepared foods.[100] It is hypothesized that the Danish government'sefforts to decrease trans fat intake from 6g to 1g per day over 20 years is related to a 50% decrease in deaths fromischemic heart disease.[101]

IcelandTotal ban on trans fats.

SwedenTotal ban on trans fats.

SwitzerlandSwitzerland followed Denmark's trans fats ban, and implemented its own beginning in April 2008.[102]

European UnionIn 2004, the European Food Safety Authority produced a scientific opinion on trans fatty acids.[103]

United KingdomIn October 2005, the Food Standards Agency (FSA) asked for better labelling in the UK.[104] In the July 29, 2006edition of the British Medical Journal, an editorial also called for better labelling.[105] In January 2007, the BritishRetail Consortium announced that major UK retailers, including Asda, Boots, Co-op, Iceland, Marks and Spencer,Sainsbury's, Tesco and Waitrose intended to cease adding trans fatty acids to their own products by the end of2007.[106]

Sainsbury's became the first UK major retailer to ban all trans fat from all their own brand foods.On 13 December 2007, the Food Standards Agency issued news releases stating that voluntary measures to reducetrans fats in food had already resulted in safe levels of consumer intake.[107][108]

On 15 April 2010, a BMJ (British Medical Journal) editorial called for trans fats to be "virtually eliminated in theUnited Kingdom by next year".[109] This call was supported by the National Institute for Health and ClinicalExcellence (NICE) on 22 June 2010.[110]

Trans fat 57

United StatesBefore 2006, consumers in the United States could not directly determine the presence (or quantity) of trans fats infood products. This information could only be inferred from the ingredient list, notably from the partiallyhydrogenated ingredients. According to the FDA, the average American consumes 5.8 grams of trans fat per day(2.6% of energy intake)[111] Monoglycerides and diglycerides are not considered fats by the FDA, despite theirnearly equal calorie per weight contribution during actual ingestion.[112] Critically important is the apparent fact thattrans fatty acids which are part of mono- and diglycerides are not required to be listed on the ingredients label asmaking contributions to calorie count or trans fatty acid content.On July 11, 2003, the Food and Drug Administration (FDA) issued a regulation requiring manufacturers to list transfat on the Nutrition Facts panel of foods and some dietary supplements.[28][29] The new labeling rule becamemandatory across the board, even for companies that petitioned for extensions, on January 1, 2008. However, unlikein many other countries, trans fat levels of less than 0.5 grams per serving can be listed as 0 grams trans fat on thefood label.[113] According to a study published in the Journal of Public Policy & Marketing, without an interpretivefootnote or further information on recommended daily value, many consumers do not know how to interpret themeaning of trans fat content on the Nutrition Facts panel. In fact, without specific prior knowledge about trans fatand its negative health effects, consumers, including those at risk for heart disease, may misinterpret nutrientinformation provided on the panel.[30] The FDA did not approve nutrient content claims such as "trans fat free" or"low trans fat", as they could not determine a "recommended daily value". Nevertheless, the agency is planning aconsumer study to evaluate the consumer understanding of such claims and perhaps consider a regulation allowingtheir use on packaged foods.[114] However, there is no requirement to list trans fats on institutional food packaging;thus bulk purchasers such as schools, hospitals, and cafeterias are unable to evaluate the trans fat content ofcommercial food items.[115] The FDA defines trans fats as containing one or more trans linkage that are not in aconjugated system. This is an important distinction, as it distinguishes non-conjugated synthetic trans fats fromnaturally occurring fatty acids with conjugated trans double bonds, such as conjugated linoleic acid.Critics of the plan, including FDA advisor Dr. Carlos Camargo, have expressed concern that the 0.5 gram perserving threshold is too high to refer to a food as free of trans fat. This is because a person eating many servings of aproduct, or eating multiple products over the course of the day may still consume a significant amount of transfat.[31] Despite this, the FDA estimates that by 2009, trans fat labeling will have prevented from 600 to 1,200 casesof coronary heart disease and 250 to 500 deaths each year. This benefit is expected to result from consumerschoosing alternative foods lower in trans fats as well as manufacturers reducing the amount of trans fats in theirproducts.The American Medical Association supports any state and federal efforts to ban the use of artificial trans fats in U.S.restaurants and bakeries.[116]

The American Public Health Association adopted a new policy statement regarding trans fats in 2007. These newguidelines, entitled Restricting Trans Fatty Acids in the Food Supply, recommend that the government requirenutrition facts labeling of trans fats on all commercial food products. They also urge federal, state, and localgovernments to ban and monitor use of trans fats in restaurants. Furthermore, the APHA recommends barring thesales and availability of foods containing significant amounts of trans fat in public facilities including universities,prisons, and day care facilities etc.[115]

Trans fat 58

State and local regulation in the United States

The state of California and some US cities are acting to reduce consumption of trans fats. In May 2005, Tiburon,California, became the first American city wherein all restaurants voluntarily cook with trans fat-free oils.[117]

Montgomery County, Maryland approved a ban on partially hydrogenated oils, becoming the first county in thenation to restrict trans fats.[118]

New York City embarked on a campaign in 2005 to reduce consumption of trans fats, noting that heart disease is theprimary cause of resident deaths. This has included a Public education campaign (see trans fat pamphlet [119]) and arequest to restaurant owners to eliminate trans fat from their offerings voluntarily.[120] Finding that the voluntaryprogram was not successful, New York City's Board of Health in 2006 solicited public comments on a proposal toban artificial trans fats in restaurants.[121] The board voted to ban trans fat in restaurant food on December 5, 2006.New York was the first large US city to strictly limit trans fats in restaurants. Restaurants were barred from usingmost frying and spreading fats containing artificial trans fats above 0.5 g per serving on July 1, 2007, and weresupposed to have met the same target in all of their foods by July 1, 2008.[122]

The Philadelphia City Council voted unanimously to pass a ban on February 8, 2007, which was signed into law onFebruary 15, 2007, by Mayor John F. Street.[123][124] By September 1, 2007, eateries must cease frying food in transfats. A year later, trans fat must not be used as an ingredient in commercial kitchens. The law does not apply toprepackaged foods sold in the city. On October 10, 2007, the Philadelphia City Council approved the use of transfats by small bakeries throughout the city.[125]

Nassau County, A suburban county on Long Island, New York, banned trans fats in restaurants effective April 1,2008. Bakeries were granted an extension until April 1, 2011.Albany County of New York passed a ban on trans fats. The ban was adopted after a unanimous vote by the countylegislature on May 14, 2007. The decision was made after New York City's decision, but no plan has been put intoplace. Legislators received a letter from Rick J. Sampson, president and CEO of the New York State RestaurantAssociation, calling on them to "delay any action on this issue until the full impact of the New York City ban isknown."San Francisco officially asked its restaurants to stop using trans fat in January 2008. The voluntary program willgrant a city decal to restaurants that comply and apply for the decal.[126] Legislators say the next step will be amandatory ban.Chicago also considered a ban on oils containing trans fats for large chain restaurants, and finally settled on a partialban on oils and posting requirements for fast food restaurants.[127][128]

On December 19, 2006, Massachusetts state representative Peter Koutoujian filed the first state level legislation thatwould ban restaurants from preparing foods with trans fats.[129] The statewide legislation has not yet passed.However, the city of Boston did ban the sale of foods containing artificial trans fats at more than 0.5 grams perserving, which is similar to the New York City regulation; there are some exceptions for clearly labeled packagedfoods and charitable bake sales.[130]

Maryland and Vermont were considering statewide bans of trans fats as of March 2007.[131][132]

King County of Washington passed a ban on artificial trans fats effective February 1, 2009.[133]

On July 25, 2008, California became the first state to ban trans fats in restaurants effective January 1, 2010.[134]

California restaurants are prohibited from using oil, shortening, and margarine containing artificial trans fats inspreads or for frying, with the exception of deep frying doughnuts.[134][135][136] As of January 1, 2011, doughnutsand other baked goods have been prohibited from containing artificial trans fats.[134][135][136] Packaged foods are notcovered by the ban and can legally contain trans fats.[137]

Trans fat 59

Food industry response

Manufacturer responsePalm oil, a natural oil extracted from the fruit of oil palm trees that is semi-solid at room temperature (15–25 degreesCelsius), is increasingly being used as an alternative to partially hydrogenated fats in baking and processed foodapplications.[138][139] However, a 2006 study supported by the National Institutes of Health and the USDAAgricultural Research Service concluded that palm oil is not a safe substitute for partially hydrogenated fats (transfats) in the food industry, because palm oil results in adverse changes in the blood concentrations of LDL cholesteroland apolipoprotein B just as trans fat does.[140][141]

The J.M. Smucker Company, American manufacturer of Crisco (the original partially hydrogenated vegetableshortening), in 2004 released a new formulation made from solid saturated palm oil cut with soybean oil andsunflower oil. This blend yielded an equivalent shortening much like the previous partially hydrogenated Crisco, andwas labelled zero grams of trans fat per 1 tablespoon serving (as compared with 1.5 grams per tablespoon of originalCrisco).[142] As of January 24, 2007, Smucker claims that all Crisco shortening products in the US have beenreformulated to contain less than one gram of trans fat per serving while keeping saturated fat content less thanbutter.[143] The separately marketed trans fat free version introduced in 2004 was discontinued.On May 22, 2004, Unilever, the corporate descendant of Joseph Crosfield & Sons (the original producer of WilhelmNormann's hydrogenation hardened oils) announced that they have eliminated trans fats from all their margarineproducts in Canada, including their flagship Becel brand.[144]

Agribusiness giant Bunge Limited, through their Bunge Oils division, are now producing and marketing an NTproduct line of non-hydrogenated oils, margarines and shortenings, made from corn, canola, and soy oils.[145]

Since 2003,[146] Loders Croklaan, a wholly owned subsidiary of Malaysia's IOI Group has been providing trans fatfree bakery and confectionery fats, made from palm oil, for giant food companies in the United States to make lessharmful margarine.[147]

Major users' responseSome major food chains have chosen to remove or reduce trans fats in their products. In some cases these changeshave been voluntary. In other cases, however, food vendors have been targeted by legal action that has generated alot of media attention. In May 2003, BanTransFats.com Inc., a U.S. non-profit corporation, filed a lawsuit against thefood manufacturer Kraft Foods in an attempt to force Kraft to remove trans fats from the Oreo cookie. The lawsuitwas withdrawn when Kraft agreed to work on ways to find a substitute for the trans fat in the Oreo. In November2006, Arby's announced[148] that by May 2007, it would be eliminating trans fat from its French fries and reducing itin other products.Similarly, in 2006, the Center for Science in the Public Interest sued KFC over its use of trans fats in fried foods.[149]

Concerning their class action complaint,[150] KFC reviewed alternative oil options, saying "there are a number of factors to consider including maintaining KFC's unique taste and flavor of Colonel Sanders' Original Recipe".[151]

On October 30, 2006, KFC announced that it will replace the partially hydrogenated soybean oil it currently uses with a zero trans fat low linoleic soybean oil in all restaurants in the US by April 2007, although its biscuits will still contain trans fats.[152] Despite the US-specific nature of the lawsuit, KFC is making changes outside of the US as well; in Canada, KFC's brand owner is switching to trans fat free Canadian canola oil by early 2007.[153] Wendy's announced in June 2006 plans to eliminate trans fats from 6,300 restaurants in the United States and Canada, starting in August 2006.[154] In November 2006, Taco Bell made a similar announcement, promising to remove trans fat from many of their menu items by switching to canola oil. By April 2007, 15 Taco Bell menu items were completely free of trans fat. In January 2007, McDonald's announced they will start phasing out the trans fat in their fries after years of testing and several delays.[155] This can be partially attributed to New York's recent ban, with the company stating they would not be selling a unique oil just for New York customers but would implement a nationwide

Trans fat 60

change. Chick-fil-A's menu is trans fat free as of October 9, 2007.[156] Raising Canes fast food chicken restaurantrecently tested a trans fat free chicken strip, but there is no plan to reduce their current menu due to the new stripbeing considered to taste "unsatisfactory."In response to a May 2007 law suit from the Center for Science in the Public Interest, Burger King announced thatits 7,100 US restaurants will begin the switch to zero trans fat oil by the end of 2007.[157]

The Walt Disney Company announced that they will begin getting rid of trans fats in meals at US theme parks by theend of 2007, and will stop the inclusion of trans fats in licensed or promotional products by 2008.[158]

The Girl Scouts of the USA announced in November 2006 that all of their cookies will contain less than 0.5g transfats per serving, thus meeting or exceeding the FDA guidelines for the "zero trans fat" designation.[159]

Health Canada's monitoring program, which tracks the changing amounts of TFA and SFA in fast and preparedfoods shows considerable progress in TFA reduction by some industrial users while others lag behind. In manycases, SFAs are being substituted for the TFAs.[160][161]

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[158] "The Walt Disney Company Introduces New Food Guidelines To Promote Healthier Kids' Diets" (http:/ / www. magicalmountain. net/WDWNewsDetail. asp?page=24& NewsID=1341& type=1& tag=) (Press release). Walt Disney Company. 2006-10-16. . Retrieved2007-09-12.

[159] "Statement from GSUSA CEO Kathy Cloninger: Girl Scout Cookies Now Have Zero Trans Fats" (http:/ / www. girlscouts. org/ news/news_releases/ 2006/ gs_cookies_now_have_zero_trans_fats. asp) (Press release). 2006-11-13. . Retrieved 2008-02-26.

[160] "Trans Fat Monitoring Program" (http:/ / www. hc-sc. gc. ca/ fn-an/ nutrition/ gras-trans-fats/ tfa-age_e. html). Health Canada. .[161] "Trans-fat levels dropping, though Burger King in the hot seat" (http:/ / www. cbc. ca/ health/ story/ 2007/ 12/ 20/ transfats-monitoring.

html). CBC News. 2007-12-20. . Retrieved 2007-12-21.

Further reading• Dijkstra Albert, Hamilton Richard J., Hamm Wolf (eds.) (2008). Trans Fatty Acids. Blackwell.

ISBN 978-1-4051-5691-2.• Jang ES, Jung MY, Min DB (2005). "Hydrogenation for Low Trans and High Conjugated Fatty Acids" (http:/ /

members. ift. org/ NR/ rdonlyres/ 27B49B9B-EA63-4D73-BAB4-42FEFCD72C68/ 0/crfsfsv4n1p00220030ms20040577. pdf) (PDF). Comprehensive Reviews in Food Science and Food Safety 1.

External links• "Ban the Trans: These Sorry Lipids Should Go Away" (http:/ / www. voicemagazine. org/ articles/ articledisplay.

php?ART=5145)• Center for Science in the Public Interest Trans Fat Page (http:/ / www. cspinet. org/ transfat/ )• Federal Register — 68 FR 41433 July 11, 2003: Food Labeling; Trans Fatty Acids in Nutrition Labeling;

Consumer Research to Consider Nutrient Content and Health Claims and Possible Footnote or DisclosureStatements; Final Rule and Proposed Rule (http:/ / www. fda. gov/ Food/ LabelingNutrition/ LabelClaims/NutrientContentClaims/ ucm110179)

Omega-6 fatty acid 67

Omega-6 fatty acid

The chemical structure of linoleic acid, a common n−6 fatty acid found in many vegetableoils.

n−6 fatty acids (popularly referred toas ω−6 fatty acids or omega-6 fattyacids) are a family of unsaturated fattyacids that have in common a finalcarbon–carbon double bond in the n−6position, that is, the sixth bond,counting from the methyl end.[1]

The biological effects of the n−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind todiverse receptors found in every tissue of the body. The conversion of tissue arachidonic acid (20:4n-6) to n-6prostaglandin and n-6 leukotriene hormones provides many targets for pharmaceutical drug development andtreatment to diminish excessive n-6 actions in atherosclerosis,[2] asthma, arthritis, vascular disease, thrombosis,immune-inflammatory processes, and tumor proliferation. Competitive interactions with the n−3 fatty acids affectthe relative storage, mobilization, conversion and action of the n-3 and n-6 eicosanoid precursors. (See Essentialfatty acid interactions for more information.)

Key n−6 fatty acidsLinoleic acid (18:2, n−6), the shortest-chained n−6 fatty acid, is an essential fatty acid. Arachidonic acid (20:4) is aphysiologically significant n−6 fatty acid and is the precursor for prostaglandins and other physiologically activemolecules.

Negative health effectsSome medical research suggests that excessive levels of certain n−6 fatty acids, relative to certain n−3 (Omega-3)fatty acids, may increase the probability of a number of diseases.[3][4][5]

Modern Western diets typically have ratios of n−6 to n−3 in excess of 10 to 1, some as high as 30 to 1; the averageratio of omega-6 to omega-3 in the Western diet is 15/1–16.7/1.[6] Humans are thought to have evolved with a diet ofa 1-to-1 ratio of omega-6 to omega-3 and the optimal ratio is thought to be 4 to 1 or lower,[7][6] and it is even better ifthere is more omega−3 than omega−6 (especially healthy ratio of omega−6 to omega−3 is from 1:1 to 1:4).[8] A ratioof 2–3/1 omega 6 to omega 3 helped reduce inflammation in patients with rheumatoid arthritis.[6] A ratio of 5/1 hada beneficial effect on patients with asthma but a 10/1 ratio had a negative effect.[6] A ratio of 2.5/1 reduced rectal cellproliferation in patients with colorectal cancer, whereas a ratio of 4/1 had no effect.[6]

Excess n−6 fats interfere with the health benefits of n−3 fats, in part because they compete for the same rate-limitingenzymes. A high proportion of n−6 to n−3 fat in the diet shifts the physiological state in the tissues toward thepathogenesis of many diseases: prothrombotic, proinflammatory and proconstrictive.[9]

Chronic excessive production of n−6 eicosanoids is associated with arthritis, inflammation, and cancer. Many of themedications used to treat and manage these conditions work by blocking the effects of the potent n−6 fat,arachidonic acid.[10] Many steps in formation and action of n-6 hormones from n-6 arachidonic acid proceed morevigorously than the corresponding competitive steps in formation and action of n-3 hormones from n-3eicosapentaenoic acid.[11] The COX-1 and COX-2 inhibitor medications, used to treat inflammation and pain, workby preventing the COX enzymes from turning arachidonic acid into inflammatory compounds.[12] (SeeCyclooxygenase for more information.) The LOX inhibitor medications often used to treat asthma, work bypreventing the LOX enzyme from converting arachidonic acid into the leukotrienes.[13][14] Many of the anti-maniamedications used to treat bipolar disorder work by targeting the arachidonic acid cascade in the brain.[15]

Omega-6 fatty acid 68

A high consumption of omega-6 polyunsaturated fatty acids (PUFAs), which are found in most types of vegetableoil, may increase the likelihood that postmenopausal women will develop breast cancer.[16] Similar effect wasobserved on prostate cancer.[17] Another "analysis suggested an inverse association between total polyunsaturatedfatty acids and breast cancer risk, but individual polyunsaturated fatty acids behaved differently [from each other].[...] a 20:2 derivative of linoleic acid [...] was inversely associated with the risk of breast cancer".[18]

Dietary linoleic acid requirementAdding more controversy to the n−6 fat issue is that the dietary requirement for linoleic acid (the key n−6 fatty acid),has been seriously questioned, because of a significant methodology error discovered by University of Torontoscientist Stephen Cunnane.[19] Cunnane discovered that the seminal research used to determine the dietaryrequirement for linoleic acid was based on feeding animals linoleic acid-deficient diets, which were simultaneouslydeficient in n−3 fats. The n−3 deficiency was not taken into account. The n−6 oils added back systematically tocorrect the deficiency also contained trace amounts of n−3 fats. Therefore the researchers were inadvertentlycorrecting the n−3 deficiency as well. Ultimately, it took more oil to correct both deficiencies. According toCunnane, this error overestimates linoleic acid requirements by 5 to 15 times.

Dietary sources

The evening primrose flower (O. biennis) produces anoil containing a high content of γ-linolenic acid, a type

of n−6 fatty acid.

Four major food oils (palm, soybean, rapeseed, and sunflower)provide more than 100 million metric tons annually, providingmore than 32 million metric tons of n-6 linoleic acid and 4 millionmetric tons of n-3 alpha-linolenic acid.[20]

Dietary sources of n−6 fatty acids include:[21]

•• poultry• eggs•• avocado•• nuts• cereals•• durum wheat• whole-grain breads• most vegetable oils•• evening primrose oil•• borage oil•• blackcurrant seed oil•• flax/linseed oil•• rapeseed or canola oil•• hemp oil•• soybean oil•• cottonseed oil•• sunflower seed oil•• corn oil•• safflower oil•• pumpkin seeds•• acai berry•• cashews•• pecans

Omega-6 fatty acid 69

•• pine nuts• walnuts[22]

•• spirulina• coconut[23]

List of n−6 fatty acids

Common name Lipid name Chemical name

Linoleic acid (LA) 18:2 (n−6) all-cis-9,12-octadecadienoic acid

Gamma-linolenic acid (GLA) 18:3 (n−6) all-cis-6,9,12-octadecatrienoic acid

Calendic acid 18:3 (n−6) 8E,10E,12Z-octadecatrienoic acid

Eicosadienoic acid 20:2 (n−6) all-cis-11,14-eicosadienoic acid

Dihomo-gamma-linolenic acid (DGLA) 20:3 (n−6) all-cis-8,11,14-eicosatrienoic acid

Arachidonic acid (AA) 20:4 (n−6) all-cis-5,8,11,14-eicosatetraenoic acid

Docosadienoic acid 22:2 (n−6) all-cis-13,16-docosadienoic acid

Adrenic acid 22:4 (n−6) all-cis-7,10,13,16-docosatetraenoic acid

Docosapentaenoic acid 22:5 (n−6) all-cis-4,7,10,13,16-docosapentaenoic acid

Tetracosatetraenoic acid 24:4 (n−6) all-cis-9,12,15,18-tetracosatetraenoic acid

Tetracosapentaenoic acid 24:5 (n−6) all-cis-6,9,12,15,18-tetracosapentaenoic acid

Notes & references[1] Chow, Ching Kuang (2001). Fatty Acids in Foods and Their Health Implications (http:/ / worldcat. org/ oclc/ 25508943&

referer=brief_results). New York: Routledge Publishing. .[2] Simopoulos, A. P. (October 2002). "Polyunsaturated fatty acids in biology and diseases. The importance of the ratio of omega-6/omega-3

essential fatty acids" (http:/ / www. sciencedirect. com/ science/ article/ pii/ S0753332202002536). Biomedecine & Pharmacotherapy 56 (8):365–379. doi:10.1016/S0753-3322(02)00253-6. PMID 12442909. .

[3] Lands, William E.M. (December 2005). "Dietary fat and health: the evidence and the politics of prevention: careful use of dietary fats canimprove life and prevent disease". Annals of the New York Academy of Sciences (Blackwell) 1055: 179–192. doi:10.1196/annals.1323.028.PMID 16387724.

[4] Hibbeln, Joseph R.; Nieminen, Levi R.G.; Blasbalg, Tanya L.; Riggs, Jessica A.; Lands, William E. M. (1 June 2006). "Healthy intakes ofn−3 and n−6 fatty acids: estimations considering worldwide diversity" (http:/ / www. ajcn. org/ cgi/ content/ full/ 83/ 6/ S1483). AmericanJournal of Clinical Nutrition (American Society for Nutrition) 83 (6, supplement): 1483S–1493S. PMID 16841858. .

[5] Okuyama, Hirohmi; Ichikawa, Yuko; Sun, Yueji; Hamazaki, Tomohito; Lands, William E. M. (2007). "ω3 fatty acids effectively preventcoronary heart disease and other late-onset diseases: the excessive linoleic acid syndrome". World Review of Nutritional Dietetics. WorldReview of Nutrition and Dietetics (Karger) 96 (Prevention of Coronary Heart Disease): 83–103. doi:10.1159/000097809.ISBN 3-8055-8179-3. PMID 17167282.

[6] Simopoulos, Artemis P. (October 2002). "The importance of the ratio of omega-6/omega-3 essential fatty acids". Biomedicine &Pharmacotherapy 56 (8): 365–379. doi:10.1016/S0753-3322(02)00253-6. PMID 12442909. also see the abstract of this article online (http:/ /www. ncbi. nlm. nih. gov/ pubmed/ 12442909)

[7] Daley, C. A.; Abbott, A.; Doyle, P.; Nader, G.; and Larson, S. (2004). A literature review of the value-added nutrients found in grass-fed beefproducts (http:/ / www. csuchico. edu/ agr/ grassfedbeef/ health-benefits/ index. html). California State University, Chico (College ofAgriculture). . Retrieved 2008-03-23.

[8] Lands, WEM (2005). Fish, Omega 3 and human health. American Oil Chemists' Society. ISBN 978-1-893997-81-3.[9] Simopoulos, Artemis P. (September 2003). "Importance of the ratio of omega-6/omega-3 essential fatty acids: evolutionary aspects". World

Review of Nutrition and Dietetics. World Review of Nutrition and Dietetics (Karger) 92 (Omega–6/Omega–3 Essential Fatty Acid Ratio: TheScientific Evidence): 1–174. doi:10.1159/000073788. ISBN 3-8055-7640-4. PMID 14579680.

[10] Smith, William L. (January 2008). "Nutritionally essential fatty acids and biologically indispensable cyclooxygenases". Trends inBiochemical Sciences (Elsevier) 33 (1): 27–37. doi:10.1016/j.tibs.2007.09.013. PMID 18155912.

[11] Wada, M.; Delong, CJ; Hong, YH; Rieke, CJ; Song, I; Sidhu, RS; Yuan, C; Warnock, M et al. (August 3 2007). "Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. Nutritionally essential

Omega-6 fatty acid 70

fatty acids and biologically indispensable cyclooxygenases". J. Biol. Chem. (ASBMB) 282 (31): 22254–22266. doi:10.1074/jbc.M703169200.PMID 17519235.

[12] Cleland, Leslie G.; James, Michael J.; Proudman, Susanna M. (January 2006). "Fish oil: what the prescriber needs to know" (http:/ /arthritis-research. com/ content/ 8/ 1/ 202). Arthritis Research & Therapy (BioMed Central) 8 (1): 202. doi:10.1186/ar1876. PMC 1526555.PMID 16542466. .

[13] Mickleborough, Timothy D. (June 2005). "Dietary omega-3 polyunsaturated fatty acid supplementation and airway hyperresponsiveness inasthma". The Journal of Asthma (Informa Healthcare) 42 (5): 305–314. doi:10.1081/JAS-200062950. PMID 16036405.

[14] Broughton, K. Shane; Johnson, Cody S.; Pace, Bobin K.; Liebman, Michael; Kleppinger, Kent M. (April 1, 2005). "Reduced asthmasymptoms with n−3 fatty acid ingestion are related to 5-series leukotriene production" (http:/ / www. ajcn. org/ cgi/ reprint/ 65/ 4/ 1011).American Journal of Clinical Nutrition (American Society for Nutrition) 65 (4): 1011–1017. PMID 9094887. .

[15] Lee, H.J.; Rao, J.S.; Rapoport, S.I.; Bazinet, R.P. (November 2007). "Antimanic therapies target brain arachidonic acid signaling: lessonslearned about the regulation of brain fatty acid metabolism". Prostaglandins, Leukotrienes and Essential Fatty Acids (Elsevier) 77 (5):239–246. doi:10.1016/j.plefa.2007.10.018. PMID 18042366.

[16] Sonestedt, Emily; Ericson, Ulrika; Gullberg, Bo; Skog, Kerstin; Olsson, Håkan; Wirfält, Elisabet (2008). "Do both heterocyclic amines andomega-6 polyunsaturated fatty acids contribute to the incidence of breast cancer in postmenopausal women of the Malmö diet and cancercohort?" (http:/ / www3. interscience. wiley. com/ journal/ 120780752/ abstract). The International Journal of Cancer (UICC InternationalUnion Against Cancer) 123 (7): 1637–1643. doi:10.1002/ijc.23394. PMID 18636564. . Retrieved 2008-11-30.

[17] Yong Q. Chen, at al (2007). "Modulation of prostate cancer genetic risk by omega-3 and omega-6 fatty acids". The Journal of ClinicalInvestigation 117 (7): 1866–1875. doi:10.1172/JCI31494. PMC 1890998. PMID 17607361.

[18] Pala, Valeria; Krogh, Vittorio; Muti, Paola; Chajès, Véronique; Riboli, Elio; Micheli, Andrea; Saadatian, Mitra; Sieri, Sabina et al. (18 July2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study" (http:/ / jnci. oxfordjournals. org/ cgi/content/ full/ 93/ 14/ 1088). JNCL 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870. . Retrieved 2008-11-30.

[19] Cunnane, Stephen C. (November 2003). "Problems with essential fatty acids: time for a new paradigm?". Progress in Lipid Research 42 (6):544–568. doi:10.1016/S0163-7827(03)00038-9. PMID 14559071.

[20][20] Gunstone, Frank (December 2007) "Oilseed markets: Market update: Palm oil". INFORM (AOCS) 18(12): 835-836.[21] "Food sources of total omega 6 fatty acids" (http:/ / riskfactor. cancer. gov/ diet/ foodsources/ fatty_acids/ table2. html). . Retrieved

2011-09-04.[22] Kids veggie food, omega 6 sources (http:/ / www. kidsveggiefood. com/ omega-oils/ ) Various sources referenced inluding pine nuts, pecans

and walnuts[23] Nutrition Facts about coconut (http:/ / nutritiondata. self. com/ facts/ nut-and-seed-products/ 3106/ 2)

Additional sources• Tokar, Steve (2005-09-02). "Omega-6 fatty acids cause prostate tumor cell growth in culture" (http:/ / www.

medicalnewstoday. com/ articles/ 29976. php). Medical News Today (MediLexicon International). Retrieved2008-03-23.

• "Brain fatty acid levels linked to depression" (http:/ / www. news-medical. net/ ?id=10398). News-Medical.Net(AZoNetwork). 2005-05-25. Retrieved 2008-03-23.

• Tribole, E.F. (2006-03-27). "Excess Omega-6 Fats Thwart Health Benefits from Omega-3 Fats" (http:/ / www.bmj. com/ cgi/ eletters/ 332/ 7544/ 752#130637). British Medical Journal Rapid Responses to Hooper, et al.,2006. Retrieved 2008-03-23.

External links• Fats That Heal, Fats That Kill (http:/ / worldcat. org/ search?q=Fats+ That+ Heal,+ Fats+ That+ Kill&

qt=mozilla-search). Udo Erasmus 3rd ed. Burnaby (BC): Alive Books; 1993.

Omega-3 fatty acid 71

Omega-3 fatty acidOmega 3 fatty acids (also called ω−3 fatty acids or n−3 fatty acids[1]) are fats commonly found in marine and plantoils. They are polyunsaturated fatty acids with a double bond (C=C) starting after the third carbon atom from the endof the carbon chain. The fatty acids have two ends—the acid (COOH) end and the methyl (CH3) end. The location ofthe first double bond is counted from the methyl end, which is also known as the omega (ω) end or the n end.The potential health benefits of n-3 fatty acids supplementation are controversial. They are considered essential fattyacids, meaning that they cannot be synthesized by the human body but are vital for normal metabolism. Thoughmammals cannot synthesize n−3 fatty acids, they have a limited ability to form the long-chain n−3 fatty acidsincluding eicosapentaenoic acid (EPA, 20 carbons and 5 double bonds), docosahexaenoic acid (DHA, 22 carbonsand 6 double bonds) and α-linolenic acid (ALA, 18 carbons and 3 double bonds).Common sources of n–3 fatty acids include fish oils, algal oil, squid oil, and some plant oils such as echium oil andflaxseed oil.

Health effectsSupplementation does not appear to be associated with a lower risk of all-cause mortality.[2]

CancerThe evidence linking the consumption of fish to the risk of cancer is poor.[3] Supplementation with omega-3 fattyacids does not appear to affect this risk either.[4] A 2006 report in the Journal of the American Medical Association,in their review of literature covering cohorts from many countries with a wide variety of demographics, concludedthat there was no link between n−3 fatty acids and cancer.[5] This is similar to the findings of a review by the BritishMedical Journal of studies up to February 2002 that failed to find clear effects of long and shorter chain n−3 fats ontotal mortality, combined cardiovascular events and cancer.[6][7] In those with advanced cancer and cachexia, n-3fatty acids supplements may be of benefit, improving appetite, weight, and quality of life.[8]

A 2010 study of 3,081 women suffering from breast cancer was done to research the effects of polyunsaturated fatson breast cancer. It demonstrated that the consumption of high amounts of long chain omega-3 polyunsaturated fatsfrom food produced a 25% reduced risk of additional breast cancer events. These women were also shown to havereduced risk of "all-cause mortality". Consumption of polyunsaturated fats through fish oil supplements was notshown to decrease risk of recurring breast cancer events.[9]

Cardiovascular diseaseEvidence is mixed regarding a beneficial role for omega-3 fatty acid supplementation in preventing cardiovasculardisease (including myocardial infarction and sudden cardiac death) or stroke. Some reviews find no benefit[10][2]

while other reviews do find benefit in those at high risk.[11]

Large amounts may increase LDL (see below), up to 46%, although LDL changes from small to larger, buoyant, lessatherogenic particles.[12]

N-3 fatty acids also have mild antihypertensive effects. When subjects consumed n-3 from oily fish on a regularbasis, their systolic blood pressure was lowered by about 3.5–5.5 mmHg.[13] The 18 carbon α-linolenic acid (ALA)has not been shown to have the same cardiovascular benefits that DHA or EPA may have.[14]

Some evidence suggests that people with certain circulatory problems, such as varicose veins, may benefit from the consumption of EPA and DHA, which may stimulate blood circulation, increase the breakdown of fibrin, a compound involved in clot and scar formation, and, in addition, may reduce blood pressure.[15][16] Evidently, n−3 fatty acids reduce blood triglyceride levels,[17][18][19] and regular intake may reduce the risk of secondary and

Omega-3 fatty acid 72

primary heart attack.[20] ALA does not confer the cardiovascular health benefits of EPA and DHA.[21]

Large amounts may increase the risk of hemorrhagic stroke (see below); lower amounts are not related to thisrisk;[22] 3 grams of total EPA/DHA daily are generally recognized as safe (GRAS) with no increased risk of bleedinginvolved[23] and many studies used substantially higher doses without major side effects (for example: 4.4 gramsEPA/2.2 grams DHA in 2003 study).[24]

Omega-3 fatty acids in algal oil, fish oil, fish and seafood have been shown to lower the risk of heart attacks.[25]

Omega-6 fatty acids in sunflower oil and safflower oil may also reduce the risk of cardiovascular disease.[26]

Among n-3 fatty acids [Omega-3], neither long-chain nor short-chain forms were consistently associated with breastcancer risk. High levels of docosahexaenoic acid (DHA), however, the most abundant n-3 PUFA [Omega-3] inerythrocyte (red blood cell) membranes, were associated with a reduced risk of breast cancer.[27] The DHA obtainedthrough the consumption of polyunsaturated fatty acids is positively associated with cognitive and behavioralperformance.[28] In addition DHA is vital for the grey matter structure of the human brain, as well as retinalstimulation and neurotransmission.[29]

InflammationAlthough not confirmed as an approved health claim, current research suggests that the anti-inflammatory activity oflong-chain n−3 fatty acids may translate into clinical effects.[30] For example, there is evidence that rheumatoidarthritis sufferers taking long-chain n−3 fatty acids from sources such as fish have reduced pain compared to thosereceiving standard NSAIDs.[31] Some potential benefits have been reported in conditions such as rheumatoidarthritis.[32]

Developmental disordersAlthough not supported by current scientific evidence as a primary treatment for ADHD, autism spectrum disorders,and other developmental differences,[33][34] omega-3 fatty acids have gained popularity for children with theseconditions.[33]

Omega-3 fatty acids offer a promising complementary approach to standard treatments for ADHD anddevelopmental coordination disorder.[34] Fish oils appear to reduce ADHD-related symptoms in some children.[34]

Double blind studies have shown "medium to strong treatment effects of omega 3 fatty acids on symptoms ofADHD".[35]

There is not enough scientific evidence to support the effectiveness of n-3 fatty acids for autism spectrumdisorders.[36]

Fish oil has only a small benefit on the risk of early birth.[37][38]

Psychiatric disordersThough there is some evidence that n-3 fatty acids are connected to a variety of mental disorders,[39] there is limitedevidence that may be useful as an add-on for the treatment of depression associated with bipolar disorder.[40] Thereis preliminary evidence that EPA supplementation, either with DHA or medication, is helpful in cases ofdepression.[41]

Cognitive agingDHA has been shown to promote neurogenesis in vitro and in vivo,[42] and epidemiological studies suggest thatconsumption of omega-3 fatty acids can reduce the risk of dementia, but evidence of a treatment effect in dementiapatients is inconclusive.[43] However, clinical evidence suggests benefits of treatment specifically in patients whoshow signs of cognitive decline but who are not sufficiently impaired to meet criteria for dementia.[44]

Omega-3 fatty acid 73

Adverse effectsIn a letter published October 31, 2000,[45] the United States Food and Drug Administration Center for Food Safetyand Applied Nutrition, Office of Nutritional Products, Labeling, and Dietary Supplements noted that known orsuspected risks of EPA and DHA consumed in excess of 3 grams per day may include the possibility of:•• Increased incidence of bleeding•• Hemorrhagic stroke• Oxidation of omega-3 fatty acids, forming biologically active oxidation products•• Increased levels of low-density lipoproteins (LDL) cholesterol or apoproteins associated with LDL cholesterol

among diabetics and hyperlipidemics•• Reduced glycemic control among diabeticsSubsequent advice from the FDA and national counterparts have permitted health claims associated with hearthealth.

Chemistry

Chemical structure of alpha-linolenic acid (ALA), an essential n−3 fatty acid,(18:3Δ9c,12c,15c, which means a chain of 18 carbons with 3 double bonds on carbons

numbered 9, 12, and 15). Although chemists count from the carbonyl carbon (bluenumbering), physiologists count from the n (ω) carbon (red numbering). Note that, fromthe n end (diagram right), the first double bond appears as the third carbon-carbon bond

(line segment), hence the name "n−3". This is explained by the fact that the n end isalmost never changed during physiologic transformations in the human body, as it is more

energy-stable, and other carbohydrates compounds can be synthesized from the othercarbonyl end, for example in glycerides, or from double bonds in the middle of the chain.

Chemical structure of eicosapentaenoic acid (EPA).

Chemical structure of docosahexaenoic acid (DHA).

N−3 fatty acids that are important inhuman physiology are α-linolenic acid(18:3, n−3; ALA), eicosapentaenoicacid (20:5, n−3; EPA), anddocosahexaenoic acid (22:6, n−3;DHA). These three polyunsaturateshave either 3, 5, or 6 double bonds in acarbon chain of 18, 20, or 22 carbonatoms, respectively. As with mostnaturally-produced fatty acids, alldouble bonds are in thecis-configuration, in other words, thetwo hydrogen atoms are on the sameside of the double bond; and the doublebonds are methylene interrupted, i.e.,there are two single bonds betweeneach pair of adjacent double bonds.

List of n−3 fatty acids

This table lists several different namesfor the most common n−3 fatty acidsfound in nature.

Omega-3 fatty acid 74

Common name Lipid name Chemical name

Hexadecatrienoic acid (HTA) 16:3 (n−3) all-cis-7,10,13-hexadecatrienoic acid

α-Linolenic acid (ALA) 18:3 (n−3) all-cis-9,12,15-octadecatrienoic acid

Stearidonic acid (SDA) 18:4 (n−3) all-cis-6,9,12,15-octadecatetraenoic acid

Eicosatrienoic acid (ETE) 20:3 (n−3) all-cis-11,14,17-eicosatrienoic acid

Eicosatetraenoic acid (ETA) 20:4 (n−3) all-cis-8,11,14,17-eicosatetraenoic acid

Eicosapentaenoic acid (EPA) 20:5 (n−3) all-cis-5,8,11,14,17-eicosapentaenoic acid

Heneicosapentaenoic acid (HPA) 21:5 (n−3) all-cis-6,9,12,15,18-heneicosapentaenoic acid

Docosapentaenoic acid (DPA),Clupanodonic acid

22:5 (n−3) all-cis-7,10,13,16,19-docosapentaenoic acid

Docosahexaenoic acid (DHA) 22:6 (n−3) all-cis-4,7,10,13,16,19-docosahexaenoic acid

Tetracosapentaenoic acid 24:5 (n−3) all-cis-9,12,15,18,21-tetracosapentaenoic acid

Tetracosahexaenoic acid (Nisinic acid) 24:6 (n−3) all-cis-6,9,12,15,18,21-tetracosahexaenoic acid

Mechanism of actionThe 'essential' fatty acids were given their name when researchers found that they are essential to normal growth inyoung children and animals, though the modern definition of 'essential' is stricter. A small amount of n−3 in the diet(~1% of total calories) enabled normal growth, and increasing the amount had little to no additional effect ongrowth.[46]

Likewise, researchers found that n−6 fatty acids (such as γ-linolenic acid and arachidonic acid) play a similar role innormal growth. However, they also found that n−6 was "better" at supporting dermal integrity, renal function, andparturition. These preliminary findings led researchers to concentrate their studies on n−6, and it is only in recentdecades that n−3 has become of interest.[46]

In 1964, it was discovered that enzymes found in sheep tissues convert n−6 arachidonic acid into the inflammatoryagent called prostaglandin E2,[47] which both causes the sensation of pain and expedites healing and immuneresponse in traumatized and infected tissues.[46] By 1979, more of what are now known as eicosanoids werediscovered: thromboxanes, prostacyclins, and the leukotrienes.[46] The eicosanoids, which have important biologicalfunctions, typically have a short active lifetime in the body, starting with synthesis from fatty acids and ending withmetabolism by enzymes. However, if the rate of synthesis exceeds the rate of metabolism, the excess eicosanoidsmay have deleterious effects.[46] Researchers found that certain n−3 fatty acids are also converted into eicosanoids,but at a much slower rate. Eicosanoids made from n−3 fatty acids are often referred to as anti-inflammatory, but infact they are just less inflammatory than those made from n−6 fats. If both n−3 and n−6 fatty acids are present, theywill "compete" to be transformed,[46] so the ratio of long-chain n−3:n−6 fatty acids directly affects the type ofeicosanoids that are produced.[46]

This competition was recognized as important when it was found that thromboxane is a factor in the clumping ofplatelets, which can both cause death by thrombosis and prevent death by bleeding. Likewise, the leukotrienes werefound to be important in immune/inflammatory-system response, and therefore relevant to arthritis, lupus, asthma,and recovery from infections. These discoveries led to greater interest in finding ways to control the synthesis of n−6eicosanoids. The simplest way would be by consuming more n−3 and fewer n−6 fatty acids.[46]

They are required during the prenatal period for the formation of synapses and cell membranes. These processes arealso essential in postnatal human development for injury response of the central nervous system and retinalstimulation.[48]

Omega-3 fatty acid 75

Interconversion

Conversion efficiency of ALA to EPA and DHA

The short-chain n−3 fatty acids are converted to long-chain forms (EPA, DHA) with an efficiency below 5%[49][50]

in men, and at a greater percentage in women, which may be due to the importance for meeting the demands of thefetus and neonate for DHA.[51]

These conversions occur competitively with n−6 fatty acids, which are essential closely related chemical analoguesthat are derived from linoleic acid. Both the n−3 α-linolenic acid and n−6 linoleic acid must be obtained from food.Synthesis of the longer n−3 fatty acids from linolenic acid within the body is competitively slowed by the n−6analogues. Thus, accumulation of long-chain n−3 fatty acids in tissues is more effective when they are obtaineddirectly from food or when competing amounts of n−6 analogs do not greatly exceed the amounts of n−3.The conversion of ALA to EPA and further to DHA in humans has been reported to be limited, but varies withindividuals.[52][53] Women have higher ALA conversion efficiency than men, it is presumed due to the lower rate ofuse of dietary ALA for beta-oxidation. This suggests that biological engineering of ALA conversion efficiency ispossible. Goyens et al. argue that it is the absolute amount of ALA, rather than the ratio of n−3 and n−6 fatty acids,that controls the conversion efficiency.[54]

The n−6 to n−3 ratio

Some clinical studies[46][55][56] indicate that the ingested ratio of n−6 to n−3 (especially linoleic vs alpha-linolenic)fatty acids is important to maintaining cardiovascular health. However, two studies published in 2005 and 2007found that while n−3 polyunsaturated fatty acids are extremely beneficial in preventing heart disease in humans, thelevels of n−6 polyunsaturated fatty acids (and therefore the ratios) were insignificant.[57][58]

Both n−6 and n−3 fatty acids are essential; i.e., humans must consume them in the diets. N−6 and n−3eighteen-carbon polyunsaturated fatty acids compete for the same metabolic enzymes, thus the n−6:n−3 ratio willsignificantly influence the ratio of the ensuing eicosanoids (hormones), (e.g., prostaglandins, leukotrienes,thromboxanes, etc.), and will alter the body's metabolic function.[59] In general, grass-fed animals accumulate moren−3 than do grain-fed animals, which accumulate relatively more n−6.[60] Metabolites of n−6 are more inflammatory(esp. arachidonic acid) than those of n−3. This necessitates that n−6 and n−3 be consumed in a balanced proportion;healthy ratios of n−6:n−3 range from 1:1 to 1:4 (an individual needs more n−3 than n−6).[61] Studies suggest theevolutionary human diet, rich in game animals, seafood, and other sources of n−3, may have provided such aratio.[62][63]

Typical Western diets provide ratios of between 10:1 and 30:1 (i.e., dramatically higher levels of n−6 than n-3).[64]

The ratios of n−6 to n−3 fatty acids in some common vegetable oils are: canola 2:1, soybean 7:1, olive 3–13:1,sunflower (no n−3), flax 1:3,[65] cottonseed (almost no n−3), peanut (no n−3), grapeseed oil (almost no n−3) andcorn oil 46:1 ratio of n−6 to n−3.[66]

HistoryAlthough omega-3 fatty acids have been known as essential to normal growth and health since the 1930s, awarenessof their health benefits has dramatically increased since the 1990s.[67]

The health benefits of the long-chain omega-3 fatty acids — primarily EPA and DHA are the best known. Thesebenefits were discovered in the 1970s by researchers studying the Greenland Inuit Tribe. The Greenland Inuit peopleconsumed large amounts of fat from fish, but displayed virtually no cardiovascular disease. The high level ofomega-3 fatty acids consumed by the Inuit reducedtriglycerides, heart rate, blood pressure, and atherosclerosis.[68]

On September 8, 2004, the U.S. Food and Drug Administration gave "qualified health claim" status to EPA and DHA n−3 fatty acids, stating, "supportive but not conclusive research shows that consumption of EPA and DHA [n−3] fatty acids may reduce the risk of coronary heart disease."[69] This updated and modified their health risk

Omega-3 fatty acid 76

advice letter of 2001 (see below). As of this writing, regulatory agencies do not accept that there is sufficientevidence for any of the suggested benefits of DHA and EPA other than for cardiovascular health, and further claimsshould be treated with caution.The Canadian Government has recognized the importance of DHA omega-3 and permits the following biologicalrole claim for DHA: "DHA, an omega-3 fatty acid, supports the normal development of the brain, eyes andnerves."[70]

Dietary sources

Daily valuesAs macronutrients, fats are not assigned Dietary Reference Intakes. Macronutrients have acceptable intake (AI)levels and acceptable macronutrient distribution ranges (AMDRs) instead of RDAs. The AI for n−3 is 1.6 grams/dayfor men and 1.1 grams/day for women, while the AMDR is 0.6% to 1.2% of total energy.[71]

A growing body of literature suggests that higher intakes of α-linolenic acid (ALA), eicosapentaenoic acid (EPA),and docosahexaenoic acid (DHA) may afford some degree of protection against coronary disease. Because thephysiological potency of EPA and DHA is much greater than that of ALA, it is not possible to estimate one AMDRfor all n−3 fatty acids. Approximately 10 percent of the AMDR can be consumed as EPA and/or DHA."[71] Therewas insufficient evidence as of 2005 to set an upper tolerable limit for n−3 fatty acids.[71]

Heavy metal poisoning by the body's accumulation of traces of heavy metals, in particular mercury, lead, nickel,arsenic, and cadmium, is a possible risk from consuming fish oil supplements. Also, other contaminants (PCBs,furans, dioxins, and PBDEs) might be found, especially in less-refined fish oil supplements. In reality, however,heavy metal toxicity from consuming fish oil supplements is highly unlikely, because heavy metals selectively bindwith protein in the fish flesh rather than accumulate in the oil. An independent test in 2005 of 44 fish oils on the USmarket found all of the products passed safety standards for potential contaminants.[72]

The FDA has advised that adults can safely consume a total of 3 grams per day of combined DHA and EPA, with nomore than 2 g per day coming from dietary supplements.[73]

Throughout their history, the Council for Responsible Nutrition and the World Health Organization have publishedacceptable standards regarding contaminants in fish oil. The most stringent current standard is the International FishOils Standard.[74] Fish oils that are molecularly distilled under vacuum typically make this highest-grade, and havemeasurable levels of contaminants (measured parts per billion and parts per trillion).A recent trend has been to fortify food with n−3 fatty acid supplements. Global food companies have launched n−3fatty acid fortified bread, mayonnaise, pizza, yogurt, orange juice, children's pasta, milk, eggs, popcorn, confections,and infant formula.The American Heart Association has set up dietary recommendations for EPA and DHA due to their cardiovascularbenefits: Individuals with no history of coronary heart disease or myocardial infarction should consume oily fish orfish oils two times per week; those having been diagnosed with coronary heart disease after infarction shouldconsume 1 g EPA and DHA per day from oily fish or supplements; those wishing to lower blood triglycerides shouldconsume 2–4 g of EPA and DHA per day in the form of supplements.[75]

FishThe most widely available dietary source of EPA and DHA is cold water oily fish, such as salmon, herring, mackerel, anchovies, and sardines. Oils from these fish have a profile of around seven times as much n−3 as n−6. Other oily fish, such as tuna, also contain n−3 in somewhat lesser amounts. Consumers of oily fish should be aware of the potential presence of heavy metals and fat-soluble pollutants like PCBs and dioxins, which are known to accumulate up the food chain. After extensive review, researchers from Harvard's School of Public Health in the

Omega-3 fatty acid 77

Journal of the American Medical Association (2006) reported that the benefits of fish intake generally far outweighthe potential risks. Although fish is a dietary source of n−3 fatty acids, fish do not synthesize them; they obtain themfrom the algae (microalgae in particular) or plankton in their diets.[76]

Grams of n−3 per 3oz (85g) serving[77]

Common name grams n−3

Herring, sardines 1.3–2

Mackerel: Spanish/Atlantic/Pacific 1.1–1.7

Salmon 1.1–1.9

Halibut 0.60–1.12

Tuna 0.21–1.1

Swordfish 0.97

Greenshell/lipped mussels 0.95[78]

Tilefish 0.9

Tuna (canned, light) 0.17–0.24

Pollock 0.45

Cod 0.15–0.24

Catfish 0.22–0.3

Flounder 0.48

Grouper 0.23

Mahi mahi 0.13

Orange roughy 0.028

Red snapper 0.29

Shark 0.83

King mackerel 0.36

Hoki (blue grenadier) 0.41[78]

Gemfish 0.40[78]

Blue eye cod 0.31[78]

Sydney rock oysters 0.30[78]

Tuna, canned 0.23[78]

Snapper 0.22[78]

Eggs, large regular 0.109[78]

Barramundi, saltwater 0.100[78]

Giant tiger prawn 0.100[78]

Lean red meat 0.031[78]

Turkey 0.030[78]

Cereals, rice, pasta, etc. 0.00[78]

Omega-3 fatty acid 78

Fruit 0.00[78]

Milk regular 0.00[78]

Regular bread 0.00[78]

Vegetables 0.00[78]

Fish oilNot all forms of fish oil may be equally digestible. Of four studies that compare bioavailability of the glyceryl esterform of fish oil vs. the ethyl ester form, two have concluded the natural glyceryl ester form is better, and the othertwo studies did not find a significant difference. No studies have shown the ethyl ester form to be superior, althoughit is cheaper to manufacture.[79][80]

KrillKrill oil is a newly discovered source of n−3 fatty acids. Various claims are made in support of krill oil as a superiorsource of n−3 fatty acids. The effect of krill oil, at a lower dose of EPA + DHA (62.8%), was demonstrated to besimilar to that of fish oil.[81]

Plant sources

Flax seeds produce linseed oil, which has a very high ALA content

These tables are incomplete.Table 1. ALA content as the percentage of the seedoil.[82]

Common name Alternative name Linnaean name % ALA

Kiwifruit Actinidia deliciosa 63[83]

Perilla shiso Perilla frutescens 61

Chia seed chia sage Salvia hispanica 58

Flax linseed Linum usitatissimum 53[84] – 59[85]

Lingonberry Cowberry Vaccinium vitis-idaea 49

Camelina Gold-of-pleasure Camelina sativa 36

Purslane Portulaca Portulaca oleracea 35

Black raspberry Rubus occidentalis 33

Hemp Cannabis sativa 19

Omega-3 fatty acid 79

Canola 9[84] – 11

Table 2. ALA content as the percentage of the whole food.[84][86]

Common name Linnaean name % ALA

Flaxseed Linum usitatissimum 18.1

Butternuts Juglans cinerea 8.7

Hempseed Cannabis sativa 8.7

Persian walnuts Juglans regia 6.3

Pecan nuts Carya illinoinensis 0.6

Hazel nuts Corylus avellana 0.1

Flaxseed (or linseed) (Linum usitatissimum) and its oil are perhaps the most widely available botanical source of then−3 fatty acid ALA. Flaxseed oil consists of approximately 55% ALA, which makes it six times richer than mostfish oils in n−3 fatty acids.[87] A portion of this is converted by the body to EPA and DHA, though this may differbetween men and women.[88]

100 g of the leaves of Purslane contains 300–400 mg ALA.[89]

EggsEggs produced by hens fed a diet of greens and insects contain higher levels of n−3 fatty acids than those producedby chickens fed corn or soybeans.[90] In addition to feeding chickens insects and greens, fish oils may be added totheir diets to increase the n-3 fatty acid concentrations in eggs.[91]

The addition of flax and canola seeds to the diets of chickens, both good sources of alpha-linolenic acid, increasesthe omega-3 content of the eggs, predominantly DHA.[92]

The addition of green algae or seaweed to the diets boosts the content of DHA and EPA content, which are the formsof omega-3 approved by the FDA for medical claims. A common consumer complaint is "Omega-3 eggs cansometimes have a fishy taste if the hens are fed marine oils."[93]

MeatOmega 3 fatty acids are formed in the chloroplasts of green leaves and algae. While seaweeds and algae are thesource of omega 3 fatty acids present in fish, grass is the source of omega 3 fatty acids present in grass fed meats.[94]

When cattle are taken off omega 3 fatty acid rich grass and shipped to a feedlot to be fattened on omega 3 fatty aciddeficient grain, they begin losing their store of this beneficial fat. Each day that an animal spends in the feedlot, theamount of omega 3 fatty acids in its meat is diminished.[95]

The n−6 to n−3 ratio of grass-fed beef is about 2:1, making it a more useful source of n−3 than grain-fed beef, whichusually has a ratio of 4:1.[60]

In a 2009 study, which was a joint effort between the USDA and researchers at Clemson University in SouthCarolina, grass-fed beef was compared with grain-finished beef and researchers found that grass-fed beef is: higherin moisture content, 42.5% lower total lipid content, 54% lower in total fatty acids, 54% higher in beta-carotene,288% higher in vitamin E (alpha-tocopherol), higher in the B-vitamins thiamin and riboflavin, higher in the mineralscalcium, magnesium, and potassium, 193% higher in total omega-3s, 117% higher in CLA (cis-9 trans-11), which isa potential cancer fighter, 90% higher in vaccenic acid (which can be transformed into CLA), lower in the saturatedfats linked with heart disease, and has a healthier ratio of omega-6 to omega-3 fatty acids (1.65 vs 4.84). Protein andcholesterol content were equal.[60]

Omega-3 fatty acid 80

In most countries, commercially available lamb is typically grass-fed, and thus higher in n−3 than other grain-fed orgrain-finished meat sources. In the United States, lamb is often finished (i.e., fattened before slaughter) with grain,resulting in lower n−3.[96]

The omega-3 content of chicken meat may be enhanced by increasing the animals' dietary intake of grains high inn−3, such as flax, chia, and canola.[97]

Kangaroo meat is also a source of n−3, with fillet and steak containing 74 mg per 100g of raw meat.[98]

Mammalian brains and eyesThe brains and eyes of mammals are extremely rich in DHA as well as other n-3 fatty acids.[99] DHA is a majorstructural component of the mammalian brain, and is in fact the most abundant (n-3) fatty acid in the brain.[100]

Seal oilSeal oil is a source of EPA, DPA, and DHA. According to Health Canada, it helps to support the development of thebrain, eyes and nerves in children up to 12 years of age.[101] However, like all seal products, it is not allowed forimport into the European Union.[102]

Other sourcesThe microalgae Crypthecodinium cohnii and Schizochytrium are rich sources of DHA, but not EPA, and can beproduced commercially in bioreactors.Oil from brown algae (kelp) is a source of EPA.In 2006 a study was published in the Journal of Dairy Science entitled "The Linear Relationship between theProportion of Fresh Grass in the Cow Diet, Milk Fatty Acid Composition, and Butter Properties". It was found thatgrass fed butter contains substantially more CLA, vitamin E, beta-carotene, and omega-3 fatty acids than butter fromcows raised in factory farms or that have limited access to pasture. It was also found that the softer the butter, themore fresh pasture in the cow’s diet. Cows that get all their nutrients from grass have the softest butterfat of all.[103]

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[65][65] Erasmus, Udo, Fats and Oils. 1986. Alive books, Vancouver, ISBN 0-920470-16-5 p. 263 (round-number ratio within ranges given.)[66] "Essential Fats in Food Oils" (http:/ / efaeducation. nih. gov/ sig/ esstable. html). National Institutes of Health. . Retrieved 2012-03-06.[67] Holman RT (February 1998). "The slow discovery of the importance of omega 3 essential fatty acids in human health". J. Nutr. 128 (2

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[73] Bent S, Bertoglio K, Hendren RL (August 2009). "Omega-3 fatty acids for autistic spectrum disorder: a systematic review". J Autism DevDisord 39 (8): 1145–54. doi:10.1007/s10803-009-0724-5. PMC 2710498. PMID 19333748.

[74] International Fish Oils Standard (http:/ / www. ifosprogram. com/ IFOS/ ConsumerReport. aspx)[75] Kris-Etherton, PM, Harris, WS, Appel LJ (2002). "Fish consumption, fish oil, omega-3 acids and cardiovascular disease". Circulation 106

(21): 2747–2757. doi:10.1161/01.CIR.0000038493.65177.94. PMID 12438303.[76] Falk-Petersen, S., S. et al. (1998). "Lipids and fatty acids in ice algae and phytoplankton from the Marginal Ice Zone in the Barents Sea"

(http:/ / cat. inist. fr/ ?aModele=afficheN& cpsidt=2356641). Polar Biology 20 (1): 41–47. doi:10.1007/s003000050274. ISSN 0722-4060. .[77] "Fish, Levels of Mercury and Omega-3 Fatty Acids" (http:/ / www. americanheart. org/ presenter. jhtml?identifier=3013797). American

Heart Association. . Retrieved October 6, 2010.[78] "Omega-3 Centre" (http:/ / web. archive. org/ web/ 20080718174524/ http:/ / www. omega-3centre. com/ sources_long_chain. html).

Omega-3 sources. Omega-3 Centre. Archived from the original (http:/ / www. omega-3centre. com/ sources_long_chain. html) on2008-07-18. . Retrieved 2008-07-27.

[79] Lawson, L.D.; Hughes, B.G. (1988). "Absorption of eicosapentaenoic acid and docosahexaenoic acid from fish oil triacylglycerols or fish oilethyl esters co-ingested with a high-fat meal". Biochem. Biophys. Res. Commun. 156 (2): 960–963. doi:10.1016/S0006-291X(88)80937-9.PMID 2847723.

[80] Beckermann, B.; Beneke, M.; Seitz, I. (1990). "Comparative bioavailability of eicosapentaenoic acid and docasahexaenoic acid fromtriglycerides, free fatty acids and ethyl esters in volunteers" (in German). Arzneimittel-Forschung 40 (6): 700–704. PMID 2144420.

[81] Ulven SM; Kirkhus, B; Lamglait, A; Basu, S; Elind, E; Haider, T; Berge, K; Vik, H et al. (January 2011). "Metabolic Effects of Krill Oil areEssentially Similar to Those of Fish Oil but at Lower Dose of EPA and DHA, in Healthy Volunteers". Lipids 46 (1): 37–46.doi:10.1007/s11745-010-3490-4. PMC 3024511. PMID 21042875.

[82] "Seed Oil Fatty Acids - SOFA Database Retrieval" (http:/ / www. bfel. de/ sofa). . In German. Google translation (http:/ / translate. google.com/ translate?tl=en& u=www. bfel. de/ sofa)

[83] http:/ / www. osel. co. nz/ content/ Product_Flyers/ Kiwifruit. pdf[84] DeFilippis, Andrew P.; Laurence S. Sperling. "Understanding omega-3's" (http:/ / web. archive. org/ web/ 20071022174611/ www. biovita.

fi/ suomi/ pdf/ understanding_omega3. pdf) (PDF). Archived from the original (http:/ / www. biovita. fi/ suomi/ pdf/ understanding_omega3.pdf) on 22 October 2007. .

[85] http:/ / www. osel. co. nz/ content/ Product_Flyers/ FlaxSeedOil. pdf[86] Wilkinson, Jennifer. "Nut Grower's Guide: The Complete Handbook for Producers and Hobbyists" (http:/ / www. publish. csiro. au/

samples/ Nut Growers GuideSample. pdf) (PDF). . Retrieved 21 October 2007.[87] Thomas Bartram (September 2002). Bartram's Encyclopedia of Herbal Medicine: The Definitive Guide to the Herbal Treatments of

Diseases. Da Capo Press. pp. 271. ISBN 978-1-56924-550-7.[88] Decsi, T.; Kennedy, K. (2011). "Sex-specific differences in essential fatty acid metabolism". American Journal of Clinical Nutrition 94

(6_Suppl): 1914S–1919S. doi:10.3945/ajcn.110.000893. PMID 22089435.

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[89] Simopoulos, A. P.; Norman, H. A.; Gillaspy, J. E.; Duke, J. A.; (August 1992). "Common purslane: a source of omega-3 fatty acids andantioxidants.". J Am Coll Nutr 11 (4): 374–382. PMID 1354675.

[90] "How Omega-6s Usurped Omega-3s In US Diet" (http:/ / www. medicalnewstoday. com/ medicalnews. php?newsid=51575). .[91] Trebunová, A.; Vasko, L.; Svedová, M.; Kasteľ, R.; Tucková, M.; Mach, P. (July 2007). "The influence of omega-3 polyunsaturated fatty

acids feeding on composition of fatty acids in fatty tissues and eggs of laying hens". Deutsche Tierärztliche Wochenschrift 114 (7): 275–279.PMID 17724936.

[92] Cherian, G. Effect of feeding full fat flax and canola seeds to laying hens on the fatty acids composition of eggs, embryos, and newlyhatched chicks. http:/ / www. fao. org/ agris/ search/ display. do?f=. / 1991/ v1717/ US9138554. xml;US9138554

[93] Sterling, Colin (2010-06-03). "Washington Post's Egg Taste Test Says Homegrown And Factory Eggs Taste The Same [UPDATED,POLL]" (http:/ / www. huffingtonpost. com/ 2010/ 06/ 03/ egg-taste-test-says-no-di_n_599286. html). Huffingtonpost.com. . Retrieved2011-01-03.

[94] http:/ / www. nature. com/ nature/ journal/ v187/ n4736/ abs/ 187511b0. html[95] Duckett, S. K., D. G. Wagner, et al. (1993). "Effects of time on feed on beef nutrient composition". J Anim Sci 71(8): 2079–88.[96] "Specially Labeled Lamb" (http:/ / www. sheep101. info/ labeledlamb. html). .[97] Azcona, J.O., Schang, M.J., Garcia, P.T., Gallinger, C., R. Ayerza (h), and Coates, W. (2008). "Omega-3 enriched broiler meat: The

influence of dietary alpha-linolenic omega-3 fatty acid sources on growth, performance and meat fatty acid composition". Canadian Journalof Animal Science, Ottawa, Ontario, Canada, 88:257–269.

[98] "Gourment Game - Amazing Nutrition Facts" (http:/ / www. macromeats-gourmetgame. com. au/ Nutrition/ AmazingNutritionFacts. aspx). .[99] "DHA in Brain and Retina Structure" (http:/ / www. dha-in-mind. com/ Portals/ 0/ PDF Files/ DHA_inbrain_and_retinastructure. pdf). .[100] "Nutrition for the Brain" (http:/ / surfer. nmr. mgh. harvard. edu/ ftp/ articles/ caudatecomm. pdf). .[101] "Natural Health Product Monograph - Seal Oil" (http:/ / www. hc-sc. gc. ca/ dhp-mps/ prodnatur/ applications/ licen-prod/ monograph/

mono_seal_oil_huile_phoque-eng. php). Health Canada. June 22, 2009. . Retrieved June 20, 2012.[102] European Parliament (9 November 2009). "MEPs adopt strict conditions for the placing on the market of seal products in the European

Union" (http:/ / www. europarl. europa. eu/ sides/ getDoc. do?pubRef=-/ / EP/ / TEXT+ IM-PRESS+ 20090504IPR54952+ 0+ DOC+ XML+V0/ / EN). Hearings. European Parliament. . Retrieved 12 March 2010.

[103] Journal of Dairy Science, 2006. 89:1956–1969. "The Linear Relationship between the Proportion of Fresh Grass in the Cow Diet, MilkFatty Acid Composition, and Butter Properties".

Further reading• Allport, Susan. The Queen of Fats: Why Omega-3s Were Removed from the Western Diet and What We Can Do

to Replace Them (http:/ / worldcat. org/ search?q=The+ Queen+ of+ Fats:+ Why+ Omega-3s+ Were+ Removed+from+ the+ Western+ Diet+ and+ What+ We+ Can+ Do+ to+ Replace+ Them& qt=mozilla-search). University ofCalifornia Press, September 2006. ISBN 978-0-520-24282-1.

• Chow, Ching Kuang. Fatty Acids in Foods and Their Health Implications (http:/ / worldcat. org/ oclc/25508943& referer=brief_results). Routledge Publishing. New York. 2001.

• Clover, Charles. The End of the Line: How overfishing is changing the world and what we eat (http:/ / worldcat.org/ oclc/ 67383509& referer=brief_results). Ebury Press, London 2004. ISBN 0-09-189780-7

• Stoll, Andrew L. The Omega-3 Connection (http:/ / worldcat. org/ search?q=The+ Omega-3+ Connection&fq=ap:Andrew+ L+ Stoll& qt=facet_ap:). Simon & Schuster 2001. ISBN 0-684-87138-6.

External links• University of Maryland Medical Center, omega-3 Fatty Acids (http:/ / www. umm. edu/ altmed/

ConsSupplements/ Omega3FattyAcidscs. html)• MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid (http:/ / www. nlm. nih.

gov/ medlineplus/ druginfo/ natural/ patient-fishoil. html)

Omega-9 fatty acid 85

Omega-9 fatty acidn−9 fatty acids (popularly referred to as ω−9 fatty acids or omega-9 fatty acids) are a family of unsaturated fattyacids which have in common a final carbon–carbon double bond in the n−9 position; that is, the ninth bond from themethyl end of the fatty acid.

BackgroundSome n−9s are common components of animal fat and vegetable oil. Two n−9 fatty acids important in industry are:• Oleic acid (18:1, n−9), which is a main component of olive oil and other monounsaturated fats• Erucic acid (22:1, n−9), which is found in rapeseed, wallflower seed, and mustard seed. Rapeseed with high

erucic acid content is grown for commercial use in paintings and coatings as a drying oil. Canola oil comes from acultivar of the rapeseed plant that has been bred, or in some cases genetically modified, to contain very littleerucic acid.

Unlike n−3 and n−6 fatty acids, n−9 fatty acids are not classed as essential fatty acids (EFA). This is both becausethey can be created by the human body from unsaturated fat, and are therefore not essential in the diet, and becausethe lack of an n−6 double bond keeps them from participating in the reactions that form the eicosanoids.Under severe conditions of EFA deprivation, mammals will elongate and desaturate oleic acid to make mead acid,(20:3, n−9).[1] This also occurs to a lesser extent in vegans, vegetarians and semi vegetarians.[2]

n−9 fatty acids

Common name Lipid name Chemical name

oleic acid 18:1 (n−9) 9-octadecenoic acid

elaidic acid 18:1 (n−9) (E)-octadec-9-enoic acid

gondoic acid 20:1 (n−9) 11-eicosenoic acid

mead acid 20:3 (n−9) 5,8,11-eicosatrienoic acid

erucic acid 22:1 (n−9) 13-docosenoic acid

nervonic acid 24:1 (n−9) 15-tetracosenoic acid

References[1] Lipomics. "Mead acid" (http:/ / www. lipomics. com/ resources/ fatty_acids/ 20_3n9. htm). . Retrieved February 14, 2006.[2] Phinney SD, Odin RS, Johnson SB, Holman RT (March 1990). "Reduced arachidonate in serum phospholipids and cholesteryl esters

associated with vegetarian diets in humans" (http:/ / www. ajcn. org/ cgi/ pmidlookup?view=long& pmid=2106775). Am. J. Clin. Nutr. 51 (3):385–92. PMID 2106775. .

• Cyberlipid Center. "Polyenoic fatty acids" (http:/ / www. cyberlipid. org/ fa/ acid0003. htm). Retrieved February11, 2006.

Fatty acid 86

Fatty acid

Butyric acid, a short-chain fatty acid

In chemistry, and especially in biochemistry, a fatty acid is acarboxylic acid with a long aliphatic tail (chain), which is eithersaturated or unsaturated. Most naturally occurring fatty acids have achain of an even number of carbon atoms, from 4 to 28.[1] Fatty acidsare usually derived from triglycerides or phospholipids. When they arenot attached to other molecules, they are known as "free" fatty acids.Fatty acids are important sources of fuel because, when metabolized,they yield large quantities of ATP. Many cell types can use eitherglucose or fatty acids for this purpose. In particular, heart and skeletalmuscle prefer fatty acids. The brain cannot use fatty acids as a source of fuel; it relies on glucose or ketone bodies.[2]

Types of fatty acids

Three dimensional representations of several fatty acids

Fatty acids that have double bonds areknown as unsaturated. Fatty acids withoutdouble bonds are known as saturated. Theydiffer in length as well.

Length of free fatty acid chains

Fatty acid chains differ by length, oftencategorized as short to very long.• Short-chain fatty acids (SCFA) are fatty

acids with aliphatic tails of fewer than sixcarbons (i.e. butyric acid).

• Medium-chain fatty acids (MCFA) arefatty acids with aliphatic tails of 6–12[3]

carbons, which can form medium-chaintriglycerides.

• Long-chain fatty acids (LCFA) are fatty acids with aliphatic tails 13 to 21 carbons.[4]

• Very long chain fatty acids (VLCFA) are fatty acids with aliphatic tails longer than 22 carbons

Fatty acid 87

Unsaturated fatty acids

Comparison of the trans isomer (top) Elaidic acid and the cis-isomer oleic acid.

Unsaturated fatty acids have one or moredouble bonds between carbon atoms. (Pairsof carbon atoms connected by double bondscan be saturated by adding hydrogen atomsto them, converting the double bonds tosingle bonds. Therefore, the double bondsare called unsaturated.)

The two carbon atoms in the chain that arebound next to either side of the double bondcan occur in a cis or trans configuration.

cis

A cis configuration means thatadjacent hydrogen atoms are on thesame side of the double bond. Therigidity of the double bond freezes itsconformation and, in the case of thecis isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The moredouble bonds the chain has in the cis configuration, the less flexibility it has. When a chain has many cisbonds, it becomes quite curved in its most accessible conformations. For example, oleic acid, with one doublebond, has a "kink" in it, whereas linoleic acid, with two double bonds, has a more pronounced bend.Alpha-linolenic acid, with three double bonds, favors a hooked shape. The effect of this is that, in restrictedenvironments, such as when fatty acids are part of a phospholipid in a lipid bilayer, or triglycerides in lipiddroplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore could affect the meltingtemperature of the membrane or of the fat.

trans

A trans configuration, by contrast, means that the next two hydrogen atoms are bound to opposite sides of thedouble bond. As a result, they do not cause the chain to bend much, and their shape is similar to straightsaturated fatty acids.

In most naturally occurring unsaturated fatty acids, each double bond has three n carbon atoms after it, for some n,and all are cis bonds. Most fatty acids in the trans configuration (trans fats) are not found in nature and are the resultof human processing (e.g., hydrogenation).The differences in geometry between the various types of unsaturated fatty acids, as well as between saturated andunsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures(such as cell membranes).

Fatty acid 88

Examples of Unsaturated Fatty Acids

Commonname

Chemical structure Δx C:D n−x

Myristoleicacid

CH3(CH2)3CH=CH(CH2)7COOH cis-Δ9 14:1 n−5

Palmitoleicacid

CH3(CH2)5CH=CH(CH2)7COOH cis-Δ9 16:1 n−7

Sapienic acid CH3(CH2)8CH=CH(CH2)4COOH cis-Δ6 16:1 n−10

Oleic acid CH3(CH2)7CH=CH(CH2)7COOH cis-Δ9 18:1 n−9

Elaidic acid CH3(CH2)7CH=CH(CH2)7COOH trans-Δ9 18:1 n−9

Vaccenic acid CH3(CH2)5CH=CH(CH2)9COOH trans-Δ11 18:1 n−7

Linoleic acid CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH cis,cis-Δ9,Δ12 18:2 n−6

Linoelaidicacid

CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH trans,trans-Δ9,Δ12 18:2 n−6

α-Linolenicacid

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH cis,cis,cis-Δ9,Δ12,Δ15 18:3 n−3

Arachidonicacid

CH3(CH2)4CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH NIST [5] cis,cis,cis,cis-Δ5Δ8,Δ11,Δ14 20:4 n−6

Eicosapentaenoicacid

CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)3COOH cis,cis,cis,cis,cis-Δ5,Δ8,Δ11,Δ14,Δ17 20:5 n−3

Erucic acid CH3(CH2)7CH=CH(CH2)11COOH cis-Δ13 22:1 n−9

Docosahexaenoicacid

CH3CH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CHCH2CH=CH(CH2)2COOH cis,cis,cis,cis,cis,cis-Δ4,Δ7,Δ10,Δ13,Δ16,Δ19 22:6 n−3

Essential fatty acids

Fatty acids that are required by the human body but cannot be made in sufficient quantity from other substrates, andtherefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids:one has a double bond three carbon atoms removed from the methyl end; the other has a double bond six carbonatoms removed from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyondcarbons 9 and 10, as counted from the carboxylic acid side.[6] Two essential fatty acids are linoleic acid (LA) andalpha-linolenic acid (ALA). They are widely distributed in plant oils. The human body has a limited ability toconvert ALA into the longer-chain n-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA),which can also be obtained from fish.

Saturated fatty acidsFor a more comprehensive list, see List of saturated fatty acids.Saturated fatty acids are long-chain carboxylic acids that usually have between 12 and 24 carbon atoms and have nodouble bonds. Thus, saturated fatty acids are saturated with hydrogen (since double bonds reduce the number ofhydrogens on each carbon). Because saturated fatty acids have only single bonds, each carbon atom within the chainhas 2 hydrogen atoms (except for the omega carbon at the end that has 3 hydrogens).

Fatty acid 89

Examples of Saturated Fatty Acids

Common name Chemical structure C:D

Caprylic acid CH3(CH2)6COOH 8:0

Capric acid CH3(CH2)8COOH 10:0

Lauric acid CH3(CH2)10COOH 12:0

Myristic acid CH3(CH2)12COOH 14:0

Palmitic acid CH3(CH2)14COOH 16:0

Stearic acid CH3(CH2)16COOH 18:0

Arachidic acid CH3(CH2)18COOH 20:0

Behenic acid CH3(CH2)20COOH 22:0

Lignoceric acid CH3(CH2)22COOH 24:0

Cerotic acid CH3(CH2)24COOH 26:0

Nomenclature

Numbering of carbon atoms

Several different systems ofnomenclature are used for fatty acids.The following table describes the mostcommon systems.

System Example Explanation

Trivialnomenclature

Palmitoleic acid Trivial names (or common names) are non-systematic historical names, which are the mostfrequent naming system used in literature. Most common fatty acids have trivial names in additionto their systematic names (see below). These names frequently do not follow any pattern, but theyare concise and often unambiguous.

Systematicnomenclature

(9Z)-octadecenoic acid Systematic names (or IUPAC names) derive from the standard IUPAC Rules for the Nomenclatureof Organic Chemistry, published in 1979,[7] along with a recommendation published specifically forlipids in 1977.[8] Counting begins from the carboxylic acid end. Double bonds are labelled withcis-/trans- notation or E-/Z- notation, where appropriate. This notation is generally more verbosethan common nomenclature, but has the advantage of being more technically clear and descriptive.

Δx

nomenclaturecis,cis-Δ9,Δ12

octadecadienoic acidIn Δx (or delta-x) nomenclature, each double bond is indicated by Δx, where the double bond islocated on the xth carbon–carbon bond, counting from the carboxylic acid end. Each double bond ispreceded by a cis- or trans- prefix, indicating the conformation of the molecule around the bond. Forexample, linoleic acid is designated "cis-Δ9, cis-Δ12 octadecadienoic acid". This nomenclature hasthe advantage of being less verbose than systematic nomenclature, but is no more technically clearor descriptive.

n−xnomenclature

n−3 n−x (n minus x; also ω−x or omega-x) nomenclature both provides names for individualcompounds and classifies them by their likely biosynthetic properties in animals. A double bond islocated on the xth carbon–carbon bond, counting from the terminal methyl carbon (designated as n orω) toward the carbonyl carbon. For example, α-Linolenic acid is classified as a n−3 or omega-3 fattyacid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−x,omega-x, or "omega" notation is common in popular nutritional literature, but IUPAC hasdeprecated it in favor of n−x notation in technical documents.[7] The most commonly researchedfatty acid biosynthetic pathways are n−3 and n−6, which are hypothesized to decrease or increase,respectively, inflammation.

Fatty acid 90

Lipid numbers 18:318:3ω618:3, cis,cis,cis-Δ9,Δ12,Δ15

Lipid numbers take the form C:D, where C is the number of carbon atoms in the fatty acid and D isthe number of double bonds in the fatty acid (if more than one, the double bonds are assumed to bemethylene interrupted, i.e., at intervals of 3 carbon atoms along the chain). This notation can beambiguous, as some different fatty acids can have the same numbers. Consequently, when ambiguityexists this notation is usually paired with either a Δx or n−x term.[7]

ProductionFatty acids are usually produced industrially by the hydrolysis of triglycerides, with the removal of glycerol (seeoleochemicals). Phospholipids represent another source. Some fatty acids are produced synthetically byhydrocarboxylation of alkenes.

Free fatty acidsThe biosynthesis of fatty acids involves the condensation of acetyl-CoA. Since this coenzyme carries atwo-carbon-atom group, almost all natural fatty acids have even numbers of carbon atoms.The "uncombined fatty acids" or "free fatty acids" found in organisms come from the breakdown of a triglyceride.Because they are insoluble in water, these fatty acids are transported (solubilized, circulated) while bound to plasmaprotein albumin. The levels of "free fatty acid" in the blood are limited by the availability of albumin binding sites.

Fatty acids in dietary fatsThe following table gives the fatty acid, vitamin E and cholesterol composition of some common dietary fats.[9] [10]

Saturated Monounsaturated Polyunsaturated Cholesterol Vitamin E

g/100g g/100g g/100g mg/100g mg/100g

Animal fats

Lard 40.8 43.8 9.6 93 0.00

Duck fat[11] 33.2 49.3 12.9 100 2.70

Butter 54.0 19.8 2.6 230 2.00

Vegetable fats

Coconut oil 85.2 6.6 1.7 0 .66

Palm oil 45.3 41.6 8.3 0 33.12

Cottonseed oil 25.5 21.3 48.1 0 42.77

Wheat germ oil 18.8 15.9 60.7 0 136.65

Soya oil 14.5 23.2 56.5 0 16.29

Olive oil 14.0 69.7 11.2 0 5.10

Corn oil 12.7 24.7 57.8 0 17.24

Sunflower oil 11.9 20.2 63.0 0 49.0

Safflower oil 10.2 12.6 72.1 0 40.68

Hemp oil 10 15 75 0

Canola/Rapeseed oil 5.3 64.3 24.8 0 22.21

Fatty acid 91

Reactions of fatty acidsFatty acids exhibit reactions like other carboxylic acid, i.e. they undergo esterification and acid-base reactions.

AcidityFatty acids do not show a great variation in their acidities, as indicated by their respective pKa. Nonanoic acid, forexample, has a pKa of 4.96, being only slightly weaker than acetic acid (4.76). As the chain length increases, thesolubility of the fatty acids in water decreases very rapidly, so that the longer-chain fatty acids have minimal effecton the pH of an aqueous solution. Even those fatty acids that are insoluble in water will dissolve in warm ethanol,and can be titrated with sodium hydroxide solution using phenolphthalein as an indicator to a pale-pink endpoint.This analysis is used to determine the free fatty acid content of fats; i.e., the proportion of the triglycerides that havebeen hydrolyzed.

Hydrogenation and hardeningHydrogenation of unsaturated fatty acids is widely practiced to give saturated fatty acids, which are less pronetoward rancidification. Since the saturated fatty acids are higher melting than the unsaturated relatives, the process iscalled hardening. This technology is used to convert vegetable oils into margarine. During partial hydrogenation,unsaturated fatty acids can be isomerized from cis to trans configuration.[12]

More forcing hydrogenation, i.e. using higher pressures of H2 and higher temperatures, converts fatty acids into fattyalcohols. Fatty alcohols are, however, more easily produced from fatty acid esters.In the Varrentrapp reaction certain unsaturated fatty acids are cleaved in molten alkali, a reaction at one time ofrelevance to structure elucidation.

Auto-oxidation and rancidityUnsaturated fatty acids undergo a chemical change known as auto-oxidation. The process requires oxygen (air) andis accelerated by the presence of trace metals. Vegetable oils resists this process because they contain antioxidants,such as tocopherol. Fats and oils often are treated with chelating agents such as citric acid to remove the metalcatalysts.

OzonolysisUnsaturated fatty acids are susceptible to degradation by ozone. This reaction is practiced in the production ofazelaic acid ((CH2)7(CO2H)2) from oleic acid.[12]

Circulation

Digestion and intakeShort- and medium-chain fatty acids are absorbed directly into the blood via intestine capillaries and travel throughthe portal vein just as other absorbed nutrients do. However, long-chain fatty acids are not directly released into theintestinal capillaries. Instead they are absorbed into the fatty walls of the intestine villi and reassembled again intotriglycerides. The triglycerides are coated with cholesterol and protein (protein coat) into a compound called achylomicron.Within the villi, the chylomicron enters a lymphatic capillary called a lacteal, which merges into larger lymphaticvessels. It is transported via the lymphatic system and the thoracic duct up to a location near the heart (where thearteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left subclavianvein. At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized forenergy.

Fatty acid 92

MetabolismFatty acids (provided either by ingestion or by drawing on triglycerides stored in fatty tissues) are distributed to cellsto serve as a fuel for muscular contraction and general metabolism. They are consumed by mitochondria to produceATP through beta oxidation.

DistributionBlood fatty acids are in different forms in different stages in the blood circulation. They are taken in through theintestine in chylomicrons, but also exist in very low density lipoproteins (VLDL) and low density lipoproteins (LDL)after processing in the liver. In addition, when released from adipocytes, fatty acids exist in the blood as free fattyacids.It is proposed that the blend of fatty acids exuded by mammalian skin, together with lactic acid and pyruvic acid, isdistinctive and enables animals with a keen sense of smell to differentiate individuals.[13]

References[1] IUPAC Compendium of Chemical Terminology (http:/ / goldbook. iupac. org/ F02330. html) (2nd ed.). International Union of Pure and

Applied Chemistry. 1997. ISBN 0-521-51150-X. . Retrieved 2007-10-31.[2] Mary K. Campbell, Shawn O. Farrell (2006). Biochemistry (5th ed.). Cengage Learning. p. 579. ISBN 0-534-40521-5.[3] Medscape: Free CME, Medical News, Full-text Journal Articles & More (http:/ / emedicine. medscape. com/ article/ 946755-overview)[4] Christopher Beermann1, J Jelinek1, T Reinecker2, A Hauenschild2, G Boehm1, and H-U Klör2, " Short term effects of dietary medium-chain

fatty acids and n-3 long-chain polyunsaturated fatty acids on the fat metabolism of healthy volunteers (http:/ / lipidworld. com/ content/ 2/ 1/10)"

[5] http:/ / webbook. nist. gov/ cgi/ cbook. cgi?Name=Arachidonic+ Acid& Units=SI[6] Cell Biology: A Short Course (http:/ / books. google. com/ books?id=3a6p9pA5gZ8C& pg=PA42)[7] Rigaudy, J.; Klesney, S.P. (1979). Nomenclature of Organic Chemistry. Pergamon. ISBN 0-08-022369-9. OCLC 5008199.[8] "The Nomenclature of Lipids. Recommendations, 1976" (http:/ / www. blackwell-synergy. com/ doi/ pdf/ 10. 1111/ j. 1432-1033. 1977.

tb11778. x). European Journal of Biochemistry 79 (1): 11–21. 1977. doi:10.1111/j.1432-1033.1977.tb11778.x. .[9] Food Standards Agency (1991). "Fats and Oils". McCance & Widdowson's the Composition of Foods. Royal Society of Chemistry.[10] Ted Altar. "More Than You Wanted To Know About Fats/Oils" (http:/ / www. efn. org/ ~sundance/ fats_and_oils. html). Sundance Natural

Foods Online. . Retrieved 2006-08-31.[11] U. S. Department of Agriculture.. "USDA National Nutrient Database for Standard Reference" (http:/ / www. nal. usda. gov/ fnic/

foodcomp/ search/ ). U. S. Department of Agriculture.. . Retrieved 2010-02-17.[12][12] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[13] "Electronic Nose Created To Detect Skin Vapors" (http:/ / www. sciencedaily. com/ releases/ 2009/ 07/ 090721091839. htm). Science Daily.

July 21, 2009. . Retrieved 2010-05-18.

External links• Lipid Library (http:/ / www. lipidlibrary. co. uk/ )• Prostaglandins, Leukotrienes & Essential Fatty Acids Journal (http:/ / intl. elsevierhealth. com/ journals/ plef/ )• Fatty Blood Acids (http:/ / www. dmfpolska. eu/ Diagnostics. html)

Essential fatty acid 93

Essential fatty acidEssential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requiresthem for good health but cannot synthesize them.[1] The term "essential fatty acid" refers to fatty acids required forbiological processes, and not those that only act as fuel.Only two EFAs are known for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6fatty acid).[2][3][4] Other fatty acids that are only "conditionally essential" include gamma-linolenic acid (an omega-6fatty acid), lauric acid (a saturated fatty acid), and palmitoleic acid (a monounsaturated fatty acid).[5]

When the two EFAs were first discovered in 1923, they were designated Vitamin F. In 1930, work by Burr G.O.,Burr M.M. and Miller E. on rats showed that the two EFAs are better classified with the fats than with thevitamins.[6]

FunctionsThe biological effects of the ω-3 and ω-6 fatty acids are mediated by their mutual interactions, see Essentialfatty acid interactions for detail.

In the body, essential fatty acids serve multiple functions. In each of these, the balance between dietary ω-3 and ω-6strongly affects function.•• They are modified to make

• the classic eicosanoids (affecting inflammation and many other cellular functions)• the endocannabinoids (affecting mood, behavior and inflammation)• the lipoxins from ω-6 EFAs and resolvins from ω-3 (in the presence of aspirin, downregulating inflammation.)• the isofurans, neurofurans, isoprostanes, hepoxilins, epoxyeicosatrienoic acids (EETs) and Neuroprotectin D

• They form lipid rafts (affecting cellular signaling)[7]

• They act on DNA (activating or inhibiting transcription factors such as NF-κB, which is linked topro-inflammatory cytokine production)[8]

Nomenclature and terminologyFatty acids are straight chain hydrocarbons possessing a carboxyl (COOH) group at one end. The carbon next to thecarboxylate is known as α, the next carbon β, and so forth. Since biological fatty acids can be of different lengths,the last position is labelled as a "ω", the last letter in the Greek alphabet. Since the physiological properties ofunsaturated fatty acids largely depend on the position of the first unsaturation relative to the end position and not thecarboxylate, the position is signified by (ω minus n). For example, the term ω-3 signifies that the first double bondexists as the third carbon-carbon bond from the terminal CH3 end (ω) of the carbon chain . The number of carbonsand the number of double bonds is also listed. ω-3 18:4 (stearidonic acid) or 18:4 ω-3 or 18:4 n−3 indicates an18-carbon chain with 4 double bonds, and with the first double bond in the third position from the CH3 end . Doublebonds are cis and separated by a single methylene (CH2) group unless otherwise noted. So in free fatty acid form, thechemical structure of stearidonic acid is:

Essential fatty acid 94

ExamplesFor complete tables of ω-3 and ω-6 essential fatty acids, see Polyunsaturated fatty acids.

The essential fatty acids start with the short chain polyunsaturated fatty acids (SC-PUFA):• ω-3 fatty acids:

• α-Linolenic acid or ALA (18:3)• ω-6 fatty acids:

• Linoleic acid or LA (18:2)These two fatty acids cannot be synthesised by humans, as humans lack the desaturase enzymes required for theirproduction.They form the starting point for the creation of longer and more desaturated fatty acids, which are also referred to aslong-chain polyunsaturated fatty acids (LC-PUFA):• ω-3 fatty acids:

• eicosapentaenoic acid or EPA (20:5)• docosahexaenoic acid or DHA (22:6)

• ω-6 fatty acids:• gamma-linolenic acid or GLA (18:3)• dihomo-gamma-linolenic acid or DGLA (20:3)• arachidonic acid or AA (20:4)

ω-9 fatty acids are not essential in humans, because humans generally possess all the enzymes required for theirsynthesis.

Essential fatty acidsMammals lack the ability to introduce double bonds in fatty acids beyond carbon 9 and 10, hence ω-6 linoleic acid(18:2,9,12), abbreviated LA, and the ω-3 linolenic acid (18:3,9,12,15), abbreviated ALA, are essential for humans inthe diet. In humans, arachidonic acid (20:4,5,8,11,14) can be synthesized from LA by desaturation and chainelongation (though some carnivores like cats cannot do this, and require arachadonate in the diet). In addition, thehuman body can make some long-chain ω-3 PUFAs (EPA and DHA) from the ω-3 ALA.Between 1930 and 1950, arachidonic acid and linolenic acid were termed 'essential' because each was more or lessable to meet the growth requirements of rats given fat-free diets. Further research has shown that human metabolismrequires both ω-3 and ω-6 fatty acids. To some extent, any ω-3 and any ω-6 can relieve the worst symptoms of fattyacid deficiency for its class. Particular fatty acids are still needed at critical life stages (e.g. lactation) and in somedisease states. In nonscientific writing, common usage is that the term essential fatty acid comprises all the ω-3 or -6fatty acids. Conjugated fatty acids like calendic acid are not normally considered essential. Authoritative sourcesinclude the whole families, without qualification.[9][10][11]

Traditionally speaking, the LC-PUFAs are not essential. See (Cunnane 2003)[12] for a discussion of the current statusof the term 'essential'. Because the LC-PUFA are sometimes required, they may be considered "conditionallyessential", or not essential to healthy adults.Essential fatty acids should not be confused with essential oils, which are "essential" in the sense of being aconcentrated essence.

Essential fatty acid 95

Food sourcesAlmost all the polyunsaturated fat in the human diet is from EFA. Some of the food sources of ω-3 and ω-6 fattyacids are fish and shellfish, flaxseed (linseed), hemp oil, soya oil, canola (rapeseed) oil, chia seeds, pumpkin seeds,sunflower seeds, leafy vegetables, and walnuts.Essential fatty acids play a part in many metabolic processes, and there is evidence to suggest that low levels ofessential fatty acids, or the wrong balance of types among the essential fatty acids, may be a factor in a number ofillnesses, including osteoporosis.[13]

Plant sources of ω-3 contain neither eicosapentaenoic acid (EPA) nor docosahexaenoic acid (DHA). The humanbody can (and in case of a purely vegetarian diet often must, unless certain algae or supplements derived from themare consumed) convert α-linolenic acid (ALA) to EPA and subsequently DHA. This however requires moremetabolic work, which is thought to be the reason that the absorption of essential fatty acids is much greater fromanimal rather than plant sources (see Fish and plants as a source of Omega-3 for more).The IUPAC Lipid Handbook [14] PDF (370 KiB) provides a very large and detailed listing of fat contents of animaland vegetable fats, including ω-3 and -6 oils. The National Institutes of Health's EFA Education group publishes'Essential Fats in Food Oils.' [15] This lists 40 common oils, more tightly focused on EFAs and sorted by n-6:3 ratio.Stuchlik and Zak, 'Vegetable Lipids as Components of Functional Food' [16] PDF (139 KiB) list notable vegetablesources of EFAs as well as commentary and an overview of the biosynthetic pathways involved. Users caninteractively search at Nutrition Data [17] for the richest food sources of particular EFAs or other nutrients. Carefulreaders will note that these sources are not in excellent agreement. EFA content of vegetable sources varies withcultivation conditions. Animal sources vary widely, both with the animal's feed and that the EFA makeup variesmarkedly with fats from different body parts.

Human healthAlmost all the polyunsaturated fats in the human diet are EFAs. Essential fatty acids play an important role in the lifeand death of cardiac cells.[18][19][20][21]

Essential fatty acid deficiencyEssential fatty acid deficiency results in a dermatitis similar to that seen in zinc or biotin deficiency.[22]:485

Treatment for depressionResearch suggests that high intakes of fish and omega-3 fatty acids are linked to decreased rates of major depression.Omega-3 fatty acids, such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) are important forenzymatic pathways required to metabolize long-chain polyunsaturated fatty acids (PUFAs). Low plasmaconcentrations of DHA predict low concentrations of cerebrospinal fluid 5-hydroxyindoleacetic acid (5-HIAA). It isfound that low concentrations of 5-HIAA in the brain is associated with depression and suicide.[23]

There are high concentrations of DHA in synaptic membranes of the brain. This is critical for synaptic transmissionand membrane fluidity. The omega-6 fatty acid to omega-3 fatty acid ratio is important to avoid imbalance ofmembrane fluidity. Membrane fluidity affects function of enzymes such as adenylate cyclase and ion channels suchas calcium, potassium, and sodium, which in turn affects receptor numbers and functioning, as well as serotoninneurotransmitter levels. It is evident that western diets are deficient in omega-3 and excessive in omega-6, andbalancing of this ratio would confer numerous health benefits.[24]

Clinical research suggests a benefit of omega-3 fatty acids in the treatment of depression during the perinatalperiod.[23] A meta analysis of trials of EPA supplements for depression in non-pregnant adults concluded thatsupplments with more than 60% EPA are effective, but those containing primarily DHA, or less than 60% EPA,were not effective.[25]

Essential fatty acid 96

Notes & references[1] Modern Nutrition in Health and Disease 6th Ed. (1980) Robert S. Goodhart and Maurice E. Shils. Lea and Febinger.

Philadelphia. ISBN 0-8121-0645-8. pp. 134-138.[2][2] Whitney Ellie and Rolfes SR Understanding Nutrition 11th Ed, California, Thomson Wadsworth, 2008 p.154.[3][3] Enig Mary G. Know your Fats Bethesda Press 2005 p.249[4] Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol.

Chem. 86 (587). http:/ / www. jbc. org/ cgi/ reprint/ 97/ 1/ 1. pdf. Retrieved 2011-11-20.[5][5] Enig 2005 p.249[6] Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (http:/ / www. jbc.

org/ cgi/ reprint/ 97/ 1/ 1. pdf) (PDF). J. Biol. Chem. 86 (587). . Retrieved 2007-01-17.[7] Stillwell W, Shaikh SR, Zerouga M, Siddiqui R, Wassall SR (2005). "Docosahexaenoic acid affects cell signaling by altering

lipid rafts". Reproduction, Nutrition, Development 45 (5): 559–79. doi:10.1051/rnd:2005046. PMID 16188208.[8] Calder PC (December 2004). "n-3 fatty acids, inflammation, and immunity--relevance to postsurgical and critically ill patients".

Lipids 39 (12): 1147–61. doi:10.1007/s11745-004-1342-z. PMID 15736910.[9] Heather Hutchins, MS, RD (10/19/2005). "Symposium Highlights -- Omega-3 Fatty Acids: Recommendations for Therapeutics

and Prevention" (http:/ / www. medscape. com/ viewarticle/ 514322_1). . "Omega-3 fatty acids and their counterparts, n-6 fatty acids,are essential polyunsaturated fatty acids (PUFA) because they cannot be synthesized de novo in the body."

[10] Nugent KP, Spigelman AD, Phillips RK (June 1996). "Tissue prostaglandin levels in familial adenomatous polyposis patientstreated with sulindac". Diseases of the Colon and Rectum 39 (6): 659–62. doi:10.1007/BF02056946. PMID 8646953."Arachidonic acid is an essential fatty acid…"

[11] Carlstedt-Duke J, Brönnegård M, Strandvik B (December 1986). "Pathological regulation of arachidonic acid release in cysticfibrosis: the putative basic defect". Proceedings of the National Academy of Sciences of the United States of America 83 (23):9202–6. doi:10.1073/pnas.83.23.9202. PMC 387103. PMID 3097647. "[T]he turnover of essential fatty acids is increased (7).Arachidonic acid is one of the essential fatty acids affected."

[12] Cunnane SC (November 2003). "Problems with essential fatty acids: time for a new paradigm?" (http:/ / linkinghub. elsevier. com/retrieve/ pii/ S0163782703000389). Progress in Lipid Research 42 (6): 544–68. doi:10.1016/S0163-7827(03)00038-9.PMID 14559071. .

[13] Kruger MC, Horrobin DF (September 1997). "Calcium metabolism, osteoporosis and essential fatty acids: a review". Progressin Lipid Research 36 (2-3): 131–51. doi:10.1016/S0163-7827(97)00007-6. PMID 9624425.

[14] http:/ / www. iupac. org/ publications/ pac/ 2001/ pdf/ 7304x0685. pdf[15] http:/ / efaeducation. nih. gov/ sig/ esstable1. html[16] http:/ / publib. upol. cz/ ~obd/ fulltext/ Biomedic146-2/ LF11_2002-1. pdf[17] http:/ / www. nutritiondata. com/ index. html[18] Honoré E, Barhanin J, Attali B, Lesage F, Lazdunski M (March 1994). "External blockade of the major cardiac

delayed-rectifier K+ channel (Kv1.5) by polyunsaturated fatty acids". Proceedings of the National Academy of Sciences of theUnited States of America 91 (5): 1937–41. doi:10.1073/pnas.91.5.1937. PMC 43279. PMID 8127910.

[19] Reiffel JA, McDonald A (August 2006). "Antiarrhythmic effects of omega-3 fatty acids". The American Journal of Cardiology98 (4A): 50i–60i. doi:10.1016/j.amjcard.2005.12.027. PMID 16919517.

[20] Landmark K, Alm CS (November 2006). "[Alpha-linolenic acid, cardiovascular disease and sudden death (http:/ / www.tidsskriftet. no/ index. php?seks_id=1446845)"] (in Norwegian). Tidsskrift for Den Norske Lægeforening 126 (21): 2792–4.PMID 17086218. .

[21] Herbaut C (September 2006). "[Omega-3 and health]" (in French). Revue médicale de Bruxelles 27 (4): S355–60.PMID 17091903.

[22] James, William; Berger, Timothy; Elston, Dirk (2005). Andrews' Diseases of the Skin: Clinical Dermatology. (10th ed.).Saunders. ISBN 0-7216-2921-0.

[23] Rees AM, Austin MP, Parker G (April 2005). "Role of omega-3 fatty acids as a treatment for depression in the perinatalperiod". The Australian and New Zealand Journal of Psychiatry 39 (4): 274–80. doi:10.1111/j.1440-1614.2005.01565.x.PMID 15777365.

[24] Logan AC (November 2004). "Omega-3 fatty acids and major depression: a primer for the mental health professional". Lipidsin Health and Disease 3 (1): 25. doi:10.1186/1476-511X-3-25. PMC 533861. PMID 15535884.

[25][25] PMID 21939614 Meta-analysis of the effects of eicosapentaenoic acid (EPA) in clinical trials in depression, 2011

Interesterified fat 97

Interesterified fatInteresterified fat is a type of oil where the fatty acids have been moved from one triglyceride molecule to another.Interesterification does not alter the fatty acids. This is generally done to modify the melting point, slowrancidification and create an oil more suitable for deep frying or making margarine with good taste and low saturatedfat content. It is not the same as partial hydrogenation which produces trans fatty acids, but interesterified fats usedin the food industry can come from hydrogenated fat, for simplicity and economic reasons.

ChemistryFats such as soybean oil consist mainly of various triglycerides which are made up of a glycerol backbone esterifiedto three fatty acid molecules. The triglycerides contain a mixture of saturated, monounsaturated and polyunsaturatedfatty acids. Interesterification is carried out by blending the desired oils and then rearranging the fatty acids over theglycerol backbone with, for instance the help of catalysts or lipase enzymes.[1] Polyunsaturated fatty acids (PUFAs)decrease the melting point of fats significantly. A triglyceride containing three saturated fatty acids is generally solidat room temperature and not very desirable for many applications. Rearranging these tryglycerides with oilscontaining unsaturated fatty acids lowers the melting point and creates fats with properties better suited for targetfood products. In addition, blending interesterified oils with liquid oils allows the reduction in saturated fatty acids inmany trans fatty acid free food products. The interesterified fats can be separated through controlled crystallization,also called fractionation.[2]

A triglyceride with a PUFA (linolenic acid) at the sn-2 position which is replaced by a saturated fatty acid (stearic acid) via interesterification.

In vegetable polyunsaturated oils, the PUFA is commonly found at the middle position (sn2) on the glycerol. Stearicacid is not usually found at sn2 in vegetable oils used in the human diet.[1]

Health effectsIn most vegetable dietary fats, palmitic (C16:0) and stearic acids (C18:0) mainly occupy the 1- and 3-positions of thetriacylglycerol molecule, whereas an unsaturated fatty acid such as oleic acid or linoleic acid usually occupies the2-position. In animal fats, this is not the case. Interesterification of vegetable oils will enhance the amount ofsaturated fatty acids at the 2-position. Fatty acids at the 2-position are biologically different from fatty acids at the 1and 3 position because they are handled differently during digestion and metabolism, and a relevant scientificquestion is whether there are health effects following from this. Although this question has received relatively littleattention in dietary fats and health research, there are a number of good controlled human intervention studies thathave addressed it.In studies addressing the health effects of interesterification as such, a diet high in interesterified fat should becompared with a diet high in a noninteresterified fat with the same fatty acid composition. If the two diets showsimilar changes in the resulting blood lipid profiles (i.e. not different from each other), this indicatesinteresterification has no effect on metabolism or biological effects. Conversely, effects of interesterification cannotbe properly addressed if the interesterified fat and the noninteresterified fat being compared have different fatty acidcompositions.

Interesterified fat 98

Zock et al.[3] compared the effects of an IE test fat with 40% C16:0 on the 2-position with a noninteresterified test fatwith only 6.5% C16:0 on the 2-position in a 3-week diet study. Despite the very high intakes and the markeddifference in positional distribution, no statistically significant effects on fasting blood lipids were observed in thegroup as a whole. Nestel et al.[4] examined the effects of an IE fat blend with 25% C16:0 on the 2-position with anative fat blend with only 9% C16:0 on the 2-position. Again, despite a high intake level and the clear difference inpositional distribution of the fats fed, no effects were observed on fasting blood lipids. Meijer and Weststrate[5]

examined the effects of interesterification, using a ‘real’ hardstock as applied in foods. The control was the same fatblend with a similar fatty acid composition, but not interesterified. The IE fat blend contained more C16:0 on the2-position (18%) than the control blend (7%). None of the fasting levels of blood lipids measured after 3 weeksshowed any change related to treatment of the fat blend. Fasting glucose level was also not affected.In 1970, Grande et al.[6] used interesterification to prepare a blend of fats and oils mimicking the fatty acidcomposition of cocoa butter. No difference between the interesterified fat blend and cocoa butter was observed inlevels of total cholesterol in fasting blood.Recently, in a study funded by the Malaysian Palm Oil Board, Sundram et al.[7] compared the effects of three typesof fat: native palm olein, a blend with partially hydrogenated soybean oil and an interesterified mixture of oils. Theyconcluded both the IE blend and the partially hydrogenated fat blend increased the fasting LDL/HDL-cholesterolratio, indicating an adverse effect on CVD risk. Sundram et al. also found that fasting plasma glucose levels werehigher after 4 weeks on the interesterified fat than after the other diets. For the postprandial study the glucoseincremental area under the curve (IAUC) following the IE meal was 40% greater than after either other meal(p<0.001), and was linked to relatively depressed insulin and C-peptide (p<0.05). As was pointed out in a letter tothe Editor by Destaillats et al.,[8] a major limitation of the Sundram study is that the diets differed in overall fattyacid composition. The interesterified fat had 30% more saturated and 57% less monounsaturated fatty acids than theuntreated palm olein. The direction of the effects on blood lipids are in line with what can be predicted based onthese differences in fatty acid content between the study diets (Mensink 2003)[9]

Another recent study by Berry et al.[10] compared shea butter (3% C18:0 on the 2-position) and interesterified sheabutter (23% C18:0 on the 2-position), while keeping overall fatty acid composition of the diets constant. This studyfound no effects of interesterification on fasting levels of blood lipids, glucose and insulin. This is line with a numberof other human intervention studies.[11][12][13][14]

Christophe et al have studied the effect of interesterification of butter oil. In a small pilot study,.[15] they observed an11% lower blood total cholesterol level after interesterification. However, in a larger, better designed study[16] thesame authors could not reproduce the cholesterol-lowering effects.

References[1] Institute of Shortenings and Edible oils (2006). "Food Fats and oils" (http:/ / www. iseo. org/ foodfatsoils. pdf). . Retrieved 2009-02-19.[2] Kellens, Marc (2000). "Interesterification Process Conditions" (http:/ / www. soci. org/ SCI/ publications/ 2001/ pdf/ pb82. pdf). . Retrieved

2007-01-29.[3] Zock PJ, de Vries JHM, de Fouw NJ, Katan MB (1995), "Positional distribution of fatty acids in dietary triglycerides: effects on fasting blood

lipoprotein concentrations in humans." (http:/ / www. ajcn. org/ cgi/ reprint/ 61/ 1/ 48. pdf), Am J Clin Nutr 61: 48–551,[4] Nestel PJ, Noakes M, Belling GB et al. (1995), "Effect on plasma lipids of interesterifying a mix of edible oils." (http:/ / www. ajcn. org/ cgi/

reprint/ 62/ 5/ 950. pdf), Am J Clin Nutr 62: 950–55,[5] Meijer GW, Weststrate JA (1997), "Interesterification of fats in margarine: effect on blood lipids, blood enzymes and hemostasis parameters."

(http:/ / www. nature. com/ ejcn/ journal/ v51/ n8/ pdf/ 1600437a. pdf), Eur J Clin Nutr 51: 527–34,[6] Grande F, Anderson JT, Keys A. (1970), "Comparison of effects of palmitic and stearic acids in the diet on serum cholesterol in man." (http:/

/ www. ajcn. org/ cgi/ reprint/ 23/ 9/ 1184. pdf), Am J Clin Nutr 23 (9): 1184–93,[7] Sundram K, Karupaiah T, Hayes K. (2007). "Stearic acid-rich interesterified fat and trans-rich fat raise the LDL/HDL ratio and plasma

glucose relative to palm olein in humans" (http:/ / www. nutritionandmetabolism. com/ content/ pdf/ 1743-7075-4-3. pdf). Nutr Metab 4: 3.doi:10.1186/1743-7075-4-3. PMC 1783656. PMID 17224066. . Retrieved 2007-01-19.

[8] Destaillats F, Moulin J, Bezelgues J-B (2007), "Letter to the editor: healthy alternatives to trans fats" (http:/ / www. nutritionandmetabolism.com/ content/ 4/ 1/ 10), Nutr and Metab 4: 10,

Interesterified fat 99

[9] Mensink RP, Zock, PL, kester AD, Katan MB. (2003), "Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDLcholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials." (http:/ / www. ajcn. org/ cgi/ reprint/ 77/ 5/ 1146.pdf), Am J Clin Nutr 77 (5): 1146–1155,

[10] Berry SEE, Miller GJ, Sanders TAB. (2007), "The solid fat content of stearic acid-rich fats determines their postprandial effects." (http:/ /www. ajcn. org/ cgi/ reprint/ 85/ 6/ 1486. pdf), Am J Clin Nutr 85: 1486–94,

[11] Zampelas A, Williams CM, Morgan LM et al. (1994), "The effect of triacylglycerol fatty acids positional distribution on postprandialplasma metabolite and hormone responses in normal adult men." (http:/ / journals. cambridge. org/ action/ displayFulltext?type=1&fid=1812280& jid=& volumeId=& issueId=03& aid=1812272& bodyId=& membershipNumber=& societyETOCSession=), Brit J Nutr 71:401–10,

[12] Yli-Jokipii K, Kallio H, Schwab U et al. (2001), "Effects of palm oil and transesterified palm oil on chylomicron and VLDL triacylglycerolstructures and postprandial lipid response." (http:/ / www. jlr. org/ cgi/ reprint/ 42/ 10/ 1618. pdf), J Lip Res 42: 1618–25,

[13] Berry SEE, Woodward R, Yeoh C, Miller GJ, Sanders TAB. (2007), "Effect of interesterification of palmitic-acid rich tryacylglycerol onpostprandial lipid and factor VII response" (http:/ / www. springerlink. com/ content/ p5475646700v5114/ fulltext. html), Lipids 42: 315–323,

[14] Summers LKM, Fielding BA, Herd SL et al. (1999), "Use of structured triacylglycerols containing predominantly stearic and oleic acids toprobe early events in metabolic processing of dietary fat" (http:/ / www. jlr. org/ cgi/ reprint/ 40/ 10/ 1890. pdf), J Lip Res 40: 1890–98,

[15] Christophe A, Matthys F, Geers R, Verdonk G. (1978), "Nutritional studies with randomised butter. Cholesterolemic effects of butter oil andrandomised butter oil in man.", Arch Intern Biophys Biochim 86: 413–15

[16] Christophe AB, De Greyt WF, Delanghe JR, Huyghebaert AD. (2000), "Substituting enzymically interesterified butter for native butter hasno effect on lipemia or lipoproteinemia in man" (http:/ / content. karger. com/ ProdukteDB/ produkte. asp?Aktion=ShowAbstract&ArtikelNr=12822& Ausgabe=224620& ProduktNr=223977), Annals of Nutr and Metab 44: 61–67,

Short-chain fatty acid

Acetic acid

Caproic acid

Short-chain fatty acids are a sub-group of fatty acids with aliphatic tails of lessthan six [1] carbons. They include:

•• Formic acid•• Propionic acid• Isobutyric acid (2-methylpropanoic acid)•• Butyric acid• Isovaleric acid (3-methylbutanoic acid)• Valeric acid (pentanoic acid)Short-chain fatty acids, just as medium-chain fatty acids, are taken up directly tothe portal vein during lipid digestion, in contrast to long-chain fatty acids, whichare packed into chylomicrons and enter lymphatic capillaries and enter the bloodfirst at the subclavian vein.

Short-chain fatty acids are produced when dietary fiber is fermented in the colon.

References[1] (http:/ / emedicine. medscape. com/ article/ 946755-overview)

External links• A review of the biological properties of SCFA from the Danone Institute (http:/ / web. archive. org/ web/

20070928224624/ http:/ / www. danone-institute. be/ communication/ pdf/ mono03/ mono3-part4. pdf) viaarchive.org

Palmitoleic acid 100

Palmitoleic acid

Palmitoleic acid

Identifiers

CAS number 373-49-9 [1] 

PubChem 445638 [2]

ChemSpider 393216 [3]

Jmol-3D images Image 1 [4]

Properties

Molecular formula C16H30O2

Molar mass 254.408

Density 0.894 g/cm³

Melting point -0.1 °C

  (verify) [5] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Palmitoleic acid, or (Z)-9-hexadecenoic acid, is an omega-7 monounsaturated fatty acid with the formulaCH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. It ispresent in all tissues, but generally found in higher concentrations in the liver. It is biosynthesized from palmitic acidby the action of the enzyme delta-9 desaturase. A beneficial fatty acid, it has been shown to increase insulinsensitivity by suppressing inflammation, as well as inhibit the destruction of insulin-secreting pancreatic beta cells.[6]

SourcesPalmitoleic acid can be abbreviated as 16:1∆9. Dietary sources of palmitoleic acid include a variety of animal oils,vegetable oils, and marine oils. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophaerhamnoides) are botanical sources with high concentrations, containing 17%[7] and 40%[8] of palmitoleic acid,respectively.

Potential biological effectsIn an analysis of numerous fatty acids, palmitoleate was shown to possibly influence fatty liverdeposition/production, insulin action, palmitate, and fatty acid synthase, leading to proposal of a new term,"lipokine" having hormone-like effects.[9]

As one such effect may include improved insulin sensitivity, palmitoleic acid (C16:1 n-7) was shown in diabetic mice to attenuate hyperglycemia and hypertriglyceridemia by increasing insulin sensitivity, in part owing to

Palmitoleic acid 101

suppression of pro-inflammatory gene expressions and improving hepatic lipid metabolism.[10]

Other preliminary research indicated that palmitoleic acid could have a role as a signaling molecule affecting bodyweight,[11] a finding consistent with previous observations that palmitoleic acid, among other fatty acids available inthe diet, may be used by enzymes affecting fat oxidation.[12] Consequently, oil types manufactured with highpalmitoleic acid content may have a role in addressing obesity.[13]

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=373-49-9[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=445638[3] http:/ / www. chemspider. com/ 393216[4] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCC%5CC%3DC%2FCCCCCC[5] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=429951085& page2=%3APalmitoleic+ acid[6] Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2

diabetes (http:/ / www. lipidworld. com/ content/ 10/ 1/ 120)[7] "Nuts, macadamia nuts, raw" (http:/ / www. nutritiondata. com/ facts/ nut-and-seed-products/ 3123/ 2). .[8] Li, Thomas S. C.; Thomas H. J. Beveridge (2003). Sea Buckthorn (Hippophae rhamnoides L.) : Production and Utilization (http:/ / www.

ovid. com/ site/ catalog/ Book/ 2738. jsp?top=2& mid=3& bottom=7& subsection=11). Ottawa, Ontario: NRC Research Press. pp. 54–55.ISBN 0-660-19007-9. .

[9] Identification of a Lipokine, a Lipid Hormone Linking Adipose Tissue to Systemic Metabolism (http:/ / www. ncbi. nlm. nih. gov/ pubmed/18805087), Department of Genetics and Complex Diseases, Harvard School of Public Health

[10] Chronic administration of palmitoleic acid reduces insulin resistance and hepatic lipid accumulation in KK-Ay Mice with genetic type 2diabetes (http:/ / www. lipidworld. com/ content/ 10/ 1/ 120), Central Research Laboratory, Tokyo Innovation Center, Nippon Suisan Kaisha

[11] Zelkowitz R (2008-09-19). "Fat molecule fights weight gain" (http:/ / sciencenow. sciencemag. org/ cgi/ content/ full/ 2008/ 919/ 3?etoc). .[12] Power, G.W., Cake, M.H. & Newsholme E.A. (1997) The influence of diet on the activity of carnitine palmitoyltransferase 1 toward a range

of acyl CoA esters. Lipids 32: 31-37[13] "Fat and Slimy" 7.30 Report, Australian Broadcasting Commission November 1995

Myristoleic acid 102

Myristoleic acid

Myristoleic acid

Identifiers

CAS number 544-64-9 [1] 

PubChem 5281119 [2]

ChemSpider 4444564 [3]

Jmol-3D images Image 1 [4]

Properties

Molecular formula C14H26O2

Molar mass 226.36

  (verify) [5] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by theenzyme delta-9 desaturase, but it is uncommon in nature.[6] One of the major sources of this fatty acid is the seed oilfrom plants of the genus Myristicaceae, comprising up to 30 per cent of the oil in some species.[7]

The cetyl ester of myristoleic acid has biological properties as an anti-inflammatory, a pain reliever, and an immunesystem modulator. (See cetyl myristoleate)

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=544-64-9[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5281119[3] http:/ / www. chemspider. com/ 4444564[4] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCC%5CC%3DC%2FCCCC[5] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=265851529& page2=%3AMyristoleic+ acid[6] Myristoleic acid (http:/ / www. lipomics. com/ fatty_acids/ 9-tetradecenoic-acid) at Lipomics.com[7] Monoenoic acids (http:/ / www. cyberlipid. org/ fa/ acid0002. htm) at CyberLipid.org

Oleic acid 103

Oleic acid

Oleic acid

Identifiers

CAS number 112-80-1 [1] 

ChEMBL CHEMBL8659 [2] 

Jmol-3D images Image 1 [3]

Properties

Molecular formula C18H34O2

Molar mass 282.4614 g/mol

Appearance Pale yellow or brownish yellow oily liquid with lard-like odor

Density 0.895 g/mL

Melting point 13-14 °C (286 K)

Boiling point 360 °C (633 K) (760mm Hg)[4]

Solubility in water Insoluble

Solubility in methanol Soluble

Hazards

MSDS JT Baker [5]

NFPA 704

  (verify) [6] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless,colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as amonounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH.[7] The term "oleic" meansrelated to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid.

Oleic acid 104

OccurrenceFatty acids (or as their salts) do not often occur as such in biological systems. Instead fatty acids like oleic acid occuras their esters, commonly the triglycerides, which are the greasy materials in many natural oils. Via the process ofsaponification, the fatty acids can be obtained.Oleic acid (as triglyceride esters) compose the majority of olive oil, although there may be less than 2.0% as freeacid in the virgin olive oil, with higher concentrations making the olive oil inedible. It also makes up 59-75% ofpecan oil,[8] 36-67% of peanut oil,[9] 15-20% of grape seed oil, sea buckthorn oil, and sesame oil,[7] and 14% ofpoppyseed oil.[10] It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat[11]

and 44 to 47% of lard.Oleic acid is the most abundant fatty acid in human adipose tissue.[12]

As an insect pheromoneOleic acid is emitted by the decaying corpses of a number of insects, including bees and Pogonomyrmex ants, andtriggers the instincts of living workers to remove the dead bodies from the hive. If a live bee[13] or ant[14][15] isdaubed with oleic acid, it is dragged off for disposal as if it were dead. The oleic acid smell also may indicate dangerto living insects, prompting them to avoid others who have succumbed to disease or places where predators lurk.[16]

Production and chemical behaviorThe biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA.In effect, stearic acid is dehydrogenated to give the monounsaturated derivative oleic acid.Oleic acid undergoes the reactions of carboxylic acids and alkenes. It is soluble in aqueous base to give soaps calledoleates. Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearicacid. Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs or drying incoatings. Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important routeto azelaic acid. The coproduct is nonanoic acid:[17]

H17C8CH=CHC7H14CO2H + 4"O" → H17C8CO2H + HO2CC7H14CO2HEsters of azelaic acid find applications in lubrication and plasticizers.The trans isomer of oleic acid is called elaidic acid (hence the name elaidinization for a reaction that converts oleicacid to elaidic acid.

UsesThe dominant use of oleic acid is as its sodium salt, which a major component of many kinds of soap. Small amountsof oleic acid are used as an excipient in pharmaceuticals, oleic acid is used as an emulsifying or solubilizing agent inaerosol products.[18] Oleic acid is also used to induce lung damage in certain types of animals, for the purpose oftesting new drugs and other means to treat lung diseases. Specifically in sheep, intravenous administration of oleicacid causes acute lung injury with corresponding pulmonary edema.[19] This sort of research has been of particularbenefit to premature newborns, for whom treatment for underdeveloped lungs (and associated complications) often isa matter of life and death.

Oleic acid 105

Health effectsPositive health effects of the substance have been documented. Oleic acid may hinder the progression ofadrenoleukodystrophy (ALD), a fatal disease that affects the brain and adrenal glands.[20] Oleic acid may beresponsible for the hypotensive (blood pressure reducing) effects of olive oil.[21] Adverse effects also have beendocumented, however, since both oleic and monounsaturated fatty acid levels in the membranes of red blood cellshave been associated with increased risk of breast cancer.[22]

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=112-80-1[2] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL8659[3] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCC%5CC%3DC%2FCCCCCCCC%28O%29%3DO[4] Oleic acid (http:/ / membership. acs. org/ c/ ccs/ pubs/ CLIPS/ JCE20020024. pdf), Chemical Laboratory Information Profile, American

Chemical Society[5] http:/ / hazard. com/ msds/ mf/ baker/ baker/ files/ o3596. htm[6] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=416953907& page2=%3AOleic+ acid[7] Alfred Thomas (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim:

Wiley-VCH. doi:10.1002/14356007.a10_173. ISBN 3-527-30673-0.[8] Villarreal, J.E., L. Lombardini, and L. Cisneros-Zevallos (2007). "Phytochemical constituents and antioxidant capacity of different pecan

[Carya illinoinensis (Wangenh.) K. Koch (http:/ / www. sciencedirect. com/ science?_ob=ArticleURL& _udi=B6T6R-4M1DB79-2&_user=952835& _coverDate=12/ 31/ 2007& _rdoc=1& _fmt=high& _orig=search& _sort=d& _docanchor=& view=c&_searchStrId=1412335994& _rerunOrigin=google& _acct=C000049198& _version=1& _urlVersion=0& _userid=952835&md5=589de1e394ce2412a09767a3b5f542be) cultivars"]. Food Chemistry 102 (4): 1241–1249. doi:10.1016/j.foodchem.2006.07.024. .

[9] http:/ / jhered. oxfordjournals. org/ cgi/ pdf_extract/ 80/ 3/ 252[10] Untoro J, Schultink W, West CE, Gross R, Hautvast JG (November 2006). "Efficacy of oral iodized peanut oil is greater than that of iodized

poppy seed oil among Indonesian schoolchildren". The American Journal of Clinical Nutrition 84 (5): 1208–14. PMID 17093176.[11] http:/ / www. springerlink. com/ content/ 0837289583682243/[12] MG Kokatnur, MC Oalmann, WD Johnson, GT Malcom and JP Strong (November 1, 1979). "Fatty acid composition of human adipose

tissue from two anatomical sites in a biracial community" (http:/ / www. ajcn. org/ cgi/ content/ abstract/ 32/ 11/ 2198). American Journal ofClinical Nutrition 32 (11): 2198–205. PMID 495536. .

[13] Anies Hannawati Purnamadjaja, R. Andrew Russell (2005). "Pheromone communication in a robot swarm: necrophoric bee behaviour andits replication". Robotica 23 (6): 731–742. doi:10.1017/S0263574704001225.

[14] Ayasse, M.; Paxton, R. (2002). "Brood protection in social insects". In Hilker, M.; Meiners, T.. Chemoecology of Insect Eggs and EggDeposition. Berlin: Blackwell. pp. 117–148. ISBN 1-4051-0694-8.

[15] Krulwich, Robert (2009). "Hey I'm Dead! The Story Of The Very Lively Ant" (http:/ / www. npr. org/ templates/ story/ story.php?storyId=102601823). NPR. .

[16] Walker, Matt (2009-09-09). "Ancient 'smell of death' revealed" (http:/ / news. bbc. co. uk/ earth/ hi/ earth_news/ newsid_8232000/ 8232607.stm). BBC - Earth News. . Retrieved 2009-09-13.

[17][17] Boy Cornils, Peter Lappe "Dicarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim.doi:10.1002/14356007.a08_523

[18] Smolinske, Susan C. (1992). Handbook of Food, Drug, and Cosmetic Excipients. pp. 247–248. ISBN 0-8493-3585-X, 9780849335853.[19] Julien M, Hoeffel JM, Flick MR (February, 1986). "Oleic acid lung injury in sheep" (http:/ / www. ncbi. nlm. nih. gov/ pubmed/ 3949648).

Journal of Applied Physiology. .[20] "Adrenoleukodystrophy: oleic acid lowers fibroblast saturated C22-26 fatty acids" (http:/ / www. ncbi. nlm. nih. gov/ pubmed/ 3951702).

National Center for Biotechnology Information. 1986-03-03. . Retrieved 2008-10-07.[21] Terés, S; Barceló-Coblijn, G; Benet, M; Alvarez, R; Bressani, R; Halver, Je; Escribá, Pv (September 2008). "Oleic acid content is

responsible for the reduction in blood pressure induced by olive oil". PNAS 105 (37): 13811–6. doi:10.1073/pnas.0807500105. PMC 2544536.PMID 18772370.

[22] Valeria Pala, Vittorio Krogh, Paola Muti, Véronique Chajès, Elio Riboli, Andrea Micheli, Mitra Saadatian, Sabina Sieri, Franco Berrino(July 18, 2001). "Erythrocyte Membrane Fatty Acids and Subsequent Breast Cancer: a Prospective Italian Study" (http:/ / jnci. oxfordjournals.org/ cgi/ content/ full/ 93/ 14/ 1088). JNCL 93 (14): 1088–95. doi:10.1093/jnci/93.14.1088. PMID 11459870. . Retrieved 2008-11-30.

Oleic acid 106

External links• (http:/ / lipidlibrary. aocs. org/ Lipids/ fa_mono/ index. htm)• NIST Chemistry Webbook (http:/ / webbook. nist. gov/ cgi/ cbook. cgi?ID=C2027476& Units=SI)

Sapienic acid

Sapienic acid

Identifiers

CAS number 17004-51-2 [1]

PubChem 5312419 [2]

ChemSpider 4471844 [3]

Jmol-3D images Image 1 [4]

Properties

Molecular formula C16H30O2

Molar mass 254.41 g mol−1

  (verify) [5] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Sapienic acid (16:1, n-10, cis-6 hexadecenoic, or sapienate) is a fatty acid that is a major component of humansebum. Sapienic acid is a sebum fatty acid that is unique to humans (thus sapien is the root of its name). Theequivalent fatty acid in mouse sebum is palmitoleic acid.[6] Sapienic acid has been implicated in the development ofacne,[7] and it may have potent antibacterial activity.[8]

Delta 6 desaturation of palmitic acid leads to the biosynthesis of sapienic acid. In other tissues linoleic acid is thetarget for delta 6 desaturase, but linoleic acid is degraded in sebaceous cells, allowing the enzyme to desaturatepalmitic to sapienic acid.[9][10] A two-carbon extension product of sapienic acid, sebaleic acid, is also present insebum.

Sapienic acid 107

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=17004-51-2[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5312419[3] http:/ / www. chemspider. com/ 4471844[4] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCC%5CC%3DC%2FCCCCCCCC[5] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=359765948& page2=%3ASapienic+ acid[6] Katsuta, Yuji; Toshii Iida, Shinji Inomata and Mitsuhiro Denda (2005). "Unsaturated Fatty Acids Induce Calcium Influx into Keratinocytes

and Cause Abnormal Differentiation of Epidermis" (http:/ / www. nature. com/ jid/ journal/ v124/ n5/ full/ 5602810a. html). Journal ofInvestigative Dermatology (Nature Publishing Group) 124 (5): 1008–1013. doi:10.1111/j.0022-202X.2005.23682.x. PMID 15854043. .

[7] Webster, Guy F.; Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. 40. CRC Press. pp. 311.ISBN 0-8247-2971-4.

[8] Drake, David R.; Kim A. Brogden, Deborah V. Dawson and Philip W. Wertz (January 2008). "Antimicrobial lipids at the skin surface" (http:// www. jlr. org/ cgi/ content/ full/ 49/ 1/ 4). Journal of Lipid Research (American Society for Biochemistry and Molecular Biology) 49 (1):4–11. doi:10.1194/jlr.R700016-JLR200. ISSN 1539-7262. PMID 17906220. .

[9] Pappas, Apostolos; Michael Anthonavage and Joel S Gordon (2002). "Metabolic Fate and Selective Utilization of Major Fatty Acids inHuman Sebaceous Gland" (http:/ / www. nature. com/ jid/ journal/ v118/ n1/ full/ 5601374a. html). Journal of Investigative Dermatology(Nature Publishing Group) 118 (1): 164–171. doi:10.1046/j.0022-202x.2001.01612.x. ISSN 1523-1747. PMID 11851890. .

[10] Ge, Lan; Joel S Gordon, Charleen Hsuan, Kurt Stenn and Stephen M Prouty (2003). "Identification of the Delta-6 Desaturase of HumanSebaceous Glands: Expression and Enzyme Activity" (http:/ / www. nature. com/ jid/ journal/ v120/ n5/ full/ 5601793a. html). Journal ofInvestigative Dermatology (Nature Publishing Group) 120 (5): 707–714. doi:10.1046/j.1523-1747.2003.12123.x. ISSN 1523-1747.PMID 12713571. .

External links• Waxes (http:/ / www. lipidlibrary. co. uk/ Lipids/ waxes/ index. htm), The Lipid Library

Elaidic acid 108

Elaidic acid

Elaidic acid

Identifiers

CAS number 112-79-8 [1] 

PubChem 637517 [2]

ChemSpider 553123 [3] 

DrugBank DB04224 [4]

KEGG C01712 [5] 

ChEBI CHEBI:27997 [6] 

ChEMBL CHEMBL460657 [7] 

Jmol-3D images Image 1 [8]

Properties

Molecular formula C18H34O2

Molar mass 282.46 g/mol

  (verify) [9] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine andbovine milk (very roughly 0.1% of the fatty acids) [10] and some meats. It is the trans isomer of oleic acid. The nameof the elaidinization reaction comes from elaidic acid.Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol.[11]

Elaidic acid 109

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=112-79-8[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=637517[3] http:/ / www. chemspider. com/ 553123[4] http:/ / www. drugbank. ca/ drugs/ DB04224[5] http:/ / www. kegg. jp/ entry/ C01712[6] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=27997[7] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL460657[8] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCC%2FC%3DC%2FCCCCCCCC[9] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443720273& page2=%3AElaidic+ acid[10] Alonso L, Fontecha J, Lozada L, Fraga MJ, Juárez M (1999). "Fatty acid composition of caprine milk: major, branched-chain, and trans fatty

acids". J. Dairy Sci. 82 (5): 878–84. doi:10.3168/jds.S0022-0302(99)75306-3. PMID 10342226.[11] Abbey M, Nestel PJ (1994). "Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic

acid in the diet". Atherosclerosis 106 (1): 99–107. doi:10.1016/0021-9150(94)90086-8. PMID 8018112.

Vaccenic acid 110

Vaccenic acid

Vaccenic acid

Identifiers

CAS number 693-72-1 [1] 

PubChem 5281127 [2]

ChemSpider 4444571 [3] 

ChEBI CHEBI:28727 [4] 

Jmol-3D images Image 1 [5]

Properties

Molecular formula C18H34O2

Molar mass 282.461 g/mol

  (verify) [6] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Vaccenic acid is an omega-7 fatty acid. It is a naturally occurring trans-fatty acid found in the fat of ruminants andin dairy products such as milk, butter, and yogurt.[7] It is also the predominant fatty acid comprising trans fat inhuman milk.[8][9]

Its IUPAC name is (E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derivedfrom the Latin vacca (cow).[10]

Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milkfat.[10] Mammals convert it into rumenic acid, a conjugated linoleic acid,[11][12] where it shows anticarcinogenicproperties.[13]

Its stereoisomer, cis-vaccenic acid, also an omega-7 fatty acid, is found in Sea Buckthorn (Hippophae rhamnoides)oil.[14] Its IUPAC name is (Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.

Vaccenic acid 111

HealthA 2008 study at the University of Alberta suggests that vaccenic acid feeding in rats over 16 weeks resulted inlowered total cholesterol, lowered LDL cholesterol and lower triglyceride levels. The researchers are preparing toconduct further research, including human clinical trials.[15]

Vaccenic acid is also found in human orbitofrontal cortex of patients with bipolar disorder and schizophrenia.[16][17]

Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may bethe cause of the phenomenon commonly known as old person smell.[18]

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=693-72-1[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5281127[3] http:/ / www. chemspider. com/ 4444571[4] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28727[5] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCC%2FC%3DC%2FCCCCCCCCCC%28O%29%3DO[6] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=477493783& page2=%3AVaccenic+ acid[7] Natural trans fats may be good for you. (http:/ / www. latimes. com/ features/ health/ la-he-eat19-2008may19,0,846200. story) May 19, 2008[8][8] Precht, D and J.Molkentin C18:1, C18:2, and C8:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid

(CLA) as well as total fat composition of German human milk lipids, Nahrung 1999 43(4) 233-244[9][9] Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006,

136 2558-2561[10] F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A

Distinct Feature of Ruminant Fats". J. Dairy Sci 88 (449).[11] Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat" (http:/ / web. archive. org/ web/ 20060907102559/ http:/

/ www. ansci. cornell. edu/ bauman/ human_health/ index. htm). Archived from the original (http:/ / www. ansci. cornell. edu/ bauman/human_health/ index. htm) on 2006-09-07. . Retrieved 2007-01-15.

[12] Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels ofconjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer 41 (1-2): 91–7.doi:10.1207/S15327914NC41-1&2_12. PMID 12094634.

[13] Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on itsconversion to cis-9, trans-11 CLA by delta9-desaturase in rats" (http:/ / jn. nutrition. org/ cgi/ content/ abstract/ 134/ 10/ 2698). J Nutr 134(10): 2698–704. PMID 15465769. . Retrieved 2007-01-15.

[14] Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database" (http:/ / www. bagkf. de/sofa/ ). .

[15] AFNS. Alberta natural trans fat research earns global recognition (http:/ / www. ales. ualberta. ca/ afns/ news. cfm?story=75846). April 2,2008.

[16] McNamara, RK; Jandacek, R; Rider, T; Tso, P; Hahn, CG; Richtand, NM; Stanford, KE (2007). "Abnormalities in the fatty acidcomposition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychoticmedications.". Schizophr Res 91 (1-3): 37–50. doi:10.1016/j.schres.2006.11.027. PMC 1853256. PMID 17236749.

[17] McNamara, RK; Jandacek, R; Rider, T; Tso, P; Stanford, KE; Hahn, CG; Richtand, NM (2008). "Deficits in docosahexaenoic acid andassociated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients withbipolar disorder.". Psychiatry Research 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMC 2620106. PMID 18715653.

[18] S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body OdorTends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520–524. doi:10.1046/j.0022-202x.2001.01287.x.PMID 11286617.

Linoelaidic acid 112

Linoelaidic acid

Linoelaidic acid[1]

Identifiers

CAS number 506-21-8 [2] 

PubChem 5282457 [3]

ChemSpider 4445609 [4] 

ChEMBL CHEMBL93204 [5] 

Jmol-3D images Image 1 [6]

Properties

Molecular formula C18H32O2

Molar mass 280.45 g/mol

Melting point −5 °C

Boiling point 229-230 °C at 16 mmHg

  (verify) [7] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Linoelaidic acid is an omega-6 trans fatty acid and is a geometric isomer of linoleic acid. It is found in partiallyhydrogenated vegetable oils.

References[1] Linoelaidic acid (http:/ / www. sigmaaldrich. com/ catalog/ search/ ProductDetail/ ALDRICH/ W338001) at Sigma-Aldrich[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=506-21-8[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5282457[4] http:/ / www. chemspider. com/ 4445609[5] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL93204[6] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCC%2FC%3DC%2FC%2FC%3DC%2FCCCCC[7] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=462091801& page2=%3ALinoelaidic+ acid

Linoleic acid 113

Linoleic acid

Linoleic acid

Identifiers

CAS number 60-33-3 [1] 

ChemSpider 4444105 [2] 

UNII 9KJL21T0QJ [3] 

KEGG C01595 [4] 

ChEBI CHEBI:17351 [5] 

ChEMBL CHEMBL267476 [6] 

Jmol-3D images Image 1 [7]

Properties

Molecular formula C18H32O2

Molar mass 280.45 g mol−1

Appearance Colorless oil

Density 0.9 g/cm3[8]

Melting point −5 °C (23 °F)[9]

−12 °C (10 °F)[8]

Boiling point 230 °C (446 °F) at 21 mbar[9]

230 °C (446 °F) at 16 mmHg[8]

Solubility in water 0.139 mg/L[9]

Vapor pressure 16 Torr at 229 °C

Hazards

Linoleic acid 114

NFPA 704

Flash point 112 °C (234 °F)[9]

  (verify) [10] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Linoleic acid (LA) is an unsaturated n-6 fatty acid. It is a colorless liquid at room temperature. In physiologicalliterature, it has a lipid number of 18:2(n-6). Chemically, linoleic acid is a carboxylic acid with an 18-carbon chainand two cis double bonds; the first double bond is located at the sixth carbon from the methyl end.[11]

Linoleic acid belongs to one of the two families of essential fatty acids. The body cannot synthesize linoleic acidfrom other food components.[12]

The word "linoleic" comes from the Greek word linon (flax). Oleic means "of, relating to, or derived from oil orolive" or "of or relating to oleic acid" because saturating the n-6 double bond produces oleic acid.

In physiologyLA is a polyunsaturated fatty acid used in the biosynthesis of arachidonic acid (AA) and thus some prostaglandins. Itis found in the lipids of cell membranes. It is abundant in many vegetable oils, comprising over half (by weight) ofpoppy seed, safflower, sunflower, and corn oils.[13]

Linoleic acid is an essential fatty acid that must be consumed for proper health. A diet only deficient in linoleatecauses mild skin scaling, hair loss,[14] and poor wound healing in rats.[15] However, achieving a deficiency in linoleicacid is nearly impossible consuming any normal diet and is thus not considered to be of clinical concern.Along with oleic acid, linoleic acid is released by cockroaches upon death which has the effect of preventing otherroaches from entering the area. This is similar to the mechanism found in ants and bees, in which oleic acid isreleased upon death.[16]

Linoleic acid 115

Metabolism and eicosanoids

The first step in the metabolism of LA is performed by Δ6desaturase, which converts LA into gamma-linolenic acid(GLA).There is evidence suggesting that infants lack Δ6desaturase of their own, and must acquire it through breast milk.Studies show that breast-milk fed babies have higher concentrations of GLA than formula-fed babies, whileformula-fed babies have elevated concentrations of LA.[17]

GLA is converted to Dihomo-gamma-linolenic acid (DGLA), which in turn is converted to arachidonic acid (AA).One of the possible fates of AA is to be transformed into a group of metabolites called eicosanoids, a class ofparacrine hormones. The three types of eicosanoids are prostaglandins, thromboxanes, and leukotrienes. Eicosanoidsproduced from AA tend to be inflammatory.[18] For example, both AA-derived thrombaxane and leukotrieneB4 areproaggretory and vasoconstrictive eicosanoids. The oxidized metabolic products of linolenic acid, such as9-hydroxyoctadecanoic acid and 13-hydroxyoctadecanoic acid, have also been shown to activate TRPV1, thecapsaicin receptor, and through this might play a major role in hyperalgesia and allodynia.[19]

An increased intake of certain [20] n–3 fatty acids with a decrease in n-6 fatty acids has been shown to attenuateinflammation due to reduced production of these eicosanoids.[21]

One study monitoring two groups of survivors of myocardial infarction concluded “the concentration ofalpha-linolenic acid was increased by 68%, in the experimental group, and that of linoleic acid reduced by 7%...thesurvivors of a first myocardial infarction, assigned to a Mediterranean alpha-linolenic acid rich diet, had a markedlyreduced rate of recurrence, other cardiac events and overall mortality.” [22]

Linoleic acid 116

Uses

Industrial usesLinoleic acid is used in making quick-drying oils, which are useful in oil paints and varnishes. These applicationsexploit the easy reaction of the linoleic acid with oxygen in air, which leads to crosslinking and formation of a stablefilm.Reduction of linoleic acid yields linoleyl alcohol.Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties onthe skin. Research points to linoleic acid's anti-inflammatory, acne reductive, and moisture retentive properties whenapplied topically on the skin.[23][24][25]

Use in researchLinoleic acid can be used to show the antioxidant effect of natural phenols. Experiments on linoleic acid subjected to2,2′-azobis (2-amidinopropane) dihydrochloride-induced oxidation with different combinations of phenolics showthat binary mixtures can lead to either a synergetic antioxidant effect or to an antagonistic effect.[26]

Linoleic acid may be linked to obesity by promoting overeating and damaging the arcuate nucleus in the brain'shypothalamus. [27]

Dietary sources

Name % LA† ref.

Salicornia oil 75%

Safflower oil 74.62%

Evening Primrose oil 73%

Poppyseed oil 70%

Grape seed oil 69.6%

Sunflower oil 65.7%

Hemp oil 60%

Corn oil 59%

Wheat germ oil 55%

Cottonseed oil 54%

Soybean oil 51%

Walnut oil 51%

Sesame oil 45%

Rice bran oil 39%

Argan oil 37%

Pistachio oil 32.7%

Peanut oil 32% [28]

Almonds 24%

Canola oil 21%

Chicken fat 18-23% [29]

Linoleic acid 117

Egg yolk 16%

Linseed oil 15%

Lard 10%

Olive oil 10% (3.5 - 21%) [30] [31]

Palm oil 10%

Cocoa butter 3%

Macadamia oil 2%

Butter 2%

Coconut oil 2%

†average val

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=60-33-3[2] http:/ / www. chemspider. com/ 4444105[3] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=9KJL21T0QJ[4] http:/ / www. kegg. jp/ entry/ C01595[5] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=17351[6] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL267476[7] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCC%2FC%3DC%5CC%2FC%3DC%5CCCCCCCCC%28%3DO%29O[8] The Merck Index, 11th Edition, 5382[9] Record of CAS RN 60-33-3 (http:/ / gestis-en. itrust. de/ nxt/ gateway. dll?f=id$t=default. htm$vid=gestiseng:sdbeng$id=014230) in the

GESTIS Substance Database from the IFA[10] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=476999843& page2=%3ALinoleic+ acid[11][11] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[12] Burr, G.O., Burr, M.M. and Miller, E. (1930). "On the nature and role of the fatty acids essential in nutrition" (http:/ / www. jbc. org/ cgi/

reprint/ 97/ 1/ 1. pdf). J. Biol. Chem. 86 (587): 1–9. .[13] U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release

20. Nutrient Data Laboratory Home Page (http:/ / www. ars. usda. gov/ ba/ bhnrc/ ndl)[14] Cunnane S, Anderson M (1 April 1997). "Pure linoleate deficiency in the rat: influence on growth, accumulation of n-6 polyunsaturates, and

(1-14C) linoleate oxidation" (http:/ / www. jlr. org/ cgi/ reprint/ 38/ 4/ 805). J Lipid Res 38 (4): 805–12. PMID 9144095. . Retrieved2007-01-15.

[15] Ruthig DJ & Meckling-Gill KA. (1 October 1999). "Both (n-3) and (n-6) fatty acids stimulate wound healing in the rat intestinal epithelialcell line, IEC-6" (http:/ / jn. nutrition. org/ cgi/ content/ full/ 129/ 10/ 1791). Journal of Nutrition 129 (10): 1791–8. PMID 10498749. .Retrieved 2007-01-15.

[16] BBC - Earth News - Ancient 'smell of death' revealed (http:/ / news. bbc. co. uk/ earth/ hi/ earth_news/ newsid_8232000/ 8232607. stm)[17] David F. Horrobin (1993). "Fatty acid metabolism in health and disease: the role of Δ-6-desaturase". American Journal of Clinical Nutrition

57: 732S–7S.[18] Piomelli, Daniele (2000). "Arachidonic Acid". Neuropsychopharmacology: The Fifth Generation of Progress. http:/ / www. acnp. org/ g4/

GN401000059/ Default. htm. Retrieved on 4/16/09.[19] Patwardhan, AM; Scotland, PE; Akopian, AN; Hargreaves, KM (2009). "Activation of TRPV1 in the spinal cord by oxidized linoleic acid

metabolites contributes to inflammatory hyperalgesia". Proceedings of the National Academy of Sciences of the United States of America 106(44): 18820–4. doi:10.1073/pnas.0905415106. PMC 2764734. PMID 19843694.

[20] Kinsella, JE; Lokesh, B; Stone, RA (1990). "Dietary n-3 polyunsaturated fatty acids and amelioration of cardiovascular disease: possiblemechanisms". The American journal of clinical nutrition 52 (1): 1–28. PMID 2193500.

[21] Kinsella John E., Lokesh Belur, Stone Richard A. (1990). "Dietary n-3 polyunsatruated fatty acids and amelioration of cardiovasculardisease: possible mechanisms". American Journal of Clinical Nutrition 52 (1): 1–28. PMID 2193500.

[22] Michel, Renaud Serge (1994). "Mediterranean alpha-linolenic acid-rich diet in secondary prevention of coronary heart disease". Lancet 343:8911.

[23] "Plant oils: Topical application and anti-inflammatory effects (croton oil test)". Dermatol. Monatsschr 179: 173. 1993.[24] Letawe,; Letawe C, Boone M, Pierard GE (March 1998). "Digital image analysis of the effect of topically applied linoleic acid on acne

microcomedones". Clinical & Experimental Dermatology 23 (2): 56–58. doi:10.1046/j.1365-2230.1998.00315.x. PMID 9692305.

Linoleic acid 118

[25] Darmstadt, G L; Darmstadt GL, Mao-Qiang M, Chi E, Saha SK, Ziboh VA, Black RE, Santosham M, Elias PM (2002). "Impact of topicaloils on the skin barrier: possible implications for neonatal health in developing countries". Acta Paediatrica 91 (5): 546–554.doi:10.1080/080352502753711678. PMID 12113324.

[26] Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic andantagonistic effects. M. N. Peyrat-Maillard, M. E. Cuvelier and C. Berset, Journal Of The American Oil Chemists' Society, 2003, Volume 80,Number 10, pages 1007-1012, doi:10.1007/s11746-003-0812-z

[27][27] Tricks Foods Play. Janet Raloff, Science News Magazine, 2012, Volume 182, Number 7, pages 25-28[28] Oil, peanut, salad or cooking: search for peanut oil on http:/ / www. nal. usda. gov/ fnic/ foodcomp/ search/[29] M. K. Nutter, E. E. Lockhart and R. S. Harris (1943). "The chemical composition of depot fats in chickens and turkeys" (http:/ / www.

springerlink. com/ content/ 0837289583682243/ ). Journal of the American Oil Chemists' Society 20 (11): 231–234.doi:10.1007/BF02630880. .

[30] "Olive Oil : Chemical Characteristics" (http:/ / www. oliveoilsource. com/ page/ chemical-characteristics). .[31] Beltran et al. (2004). Influence of Harvest Date and Crop Yield on the Fatty Acid Composition of Virgin Olive Oils from Cv. Picual (http:/ /

hera. ugr. es/ doi/ 15058025. pdf). .

External links• http:/ / lipidlibrary. aocs. org/ Lipids/ fa_poly/ index. htm

Arachidonic acid 119

Arachidonic acid

Arachidonic acid

Identifiers

CAS number 506-32-1 [1] 

PubChem 444899 [2]

ChemSpider 392692 [3] 

UNII 27YG812J1I [4] 

EC number 208-033-4 [5]

DrugBank DB04557 [6]

KEGG C00219 [7] 

MeSH Arachidonic+acid [8]

ChEBI CHEBI:36306 [9] 

ChEMBL CHEMBL15594 [10] 

RTECS number CE6675000

Beilstein Reference 1713889

3DMet B00061 [11]

Jmol-3D images Image 1 [12]

Properties

Molecular formula C20H32O2

Molar mass 304.47 g mol−1

Density 0.922 g/cm3

Melting point -49 °C, 224 K, -56 °F

Boiling point 169-171 °C, 442-444 K, 336-340 °F (at 0.15 mmHg)

log P 6.994

Arachidonic acid 120

Acidity (pKa) 4.752

Hazards

R-phrases R19

NFPA 704

Flash point 113 °C (235 °F)

  (verify) [13] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6). It is the counterpart tothe saturated arachidic acid found in peanut oil, (L. arachis – peanut.)[14]

Chemistry

In chemical structure, arachidonic acid is a carboxylic acid with a 20-carbon chain and four cis-double bonds; thefirst double bond is located at the sixth carbon from the omega end.Some chemistry sources define 'arachidonic acid' to designate any of the eicosatetraenoic acids. However, almost allwritings in biology, medicine and nutrition limit the term to all-cis-5,8,11,14-eicosatetraenoic acid.

BiologyArachidonic acid is a polyunsaturated fatty acid present in the phospholipids (especially phosphatidylethanolamine,phosphatidylcholine, and phosphatidylinositides) of membranes of the body's cells, and is abundant in the brain,muscles, liver.In addition to being involved in cellular signaling as a lipid second messenger involved in the regulation of signalingenzymes, such as PLC-γ, PLC-δ, and PKC-α, -β, and -γ isoforms, arachidonic acid is a key inflammatoryintermediate and can also act as a vasodilator.[15] (Note separate synthetic pathways, as described in section below)

Arachidonic acid 121

Essential fatty acid

Arachidonic acid in the human body usually comes from dietaryanimal sources—meat, eggs, dairy—or is synthesized from linoleic

acid.

Arachidonic acid is not one of the essential fatty acids.However, it does become essential if there is adeficiency in linoleic acid or if there is an inability toconvert linoleic acid to arachidonic acid, which isrequired by most mammals. Some mammals lack theability to—or have a very limited capacity to—convertlinoleic acid into arachidonic acid, making it anessential part of their diets. Since little or noarachidonic acid is found in common plants, suchanimals are obligate carnivores; the cat is a commonexample.[16][17] A commercial source of arachidonicacid has been derived, however, from the fungusMortierella alpina.[18]

Synthesis and cascade

Eicosanoid synthesis.

Arachidonic acid is freed from aphospholipid molecule by the enzymephospholipase A2 (PLA2), whichcleaves off the fatty acid, but can alsobe generated from DAG bydiacylglycerol lipase.[15]

Arachidonic acid generated forsignaling purposes appears to bederived by the action of aphosphatidylcholine-specific cytosolicphospholipase A2 (cPLA2, 85 kDa),whereas inflammatory arachidonic acidis generated by the action of alow-molecular-weight secretory PLA2(sPLA2, 14-18 kDa).[15]

Arachidonic acid is a precursor in theproduction of eicosanoids:

• The enzymes cyclooxygenase andperoxidase lead to prostaglandin H2,which in turn is used to produce the prostaglandins, prostacyclin, and thromboxanes.

• The enzyme 5-lipoxygenase leads to 5-HPETE, which in turn is used to produce the leukotrienes.• Arachidonic acid is also used in the biosynthesis of anandamide.• Some arachidonic acid is converted into hydroxyeicosatetraenoic acids (HETEs) and epoxyeicosatrienoic acids

(EETs) by epoxygenase.[19]

The production of these derivatives and their action in the body are collectively known as the "arachidonic acidcascade"; see essential fatty acid interactions for more details.

Arachidonic acid 122

PLA2 activationFurther information: Phospholipase_A2#RegulationPLA2, in turn, is activated by ligand binding to receptors, including:• 5-HT2 receptors [20]

• mGLUR1[20]

• bFGF receptor[20]

• IFN-α receptor[20]

• IFN-γ receptor[20]

Furthermore, any agent increasing intracellular calcium may cause activation of some forms of PLA2.[21]

PLC activationFurther information: Phospholipase C#ActivationAlternatively, arachidonic acid may be cleaved from phospholipids by phospholipase C (PLC), yieldingdiacylglycerol (DAG), which subsequently is cleaved by DAG lipase to yield arachidonic acid.[20]

Receptors that activate this pathway include:• A1 receptor[21]

• D2 receptor[21]

• α-2 adrenergic receptor[21]

• 5-HT1 receptor[21]

PLC may also be activated by MAP kinase. Activators of this pathway include PDGF and FGF.[21]

Arachidonic acid in the body

Muscle growthThrough its conversion to active components such as the prostaglandin PGF2alpha, arachidonic acid is necessary forthe repair and growth of skeletal muscle tissue.[22] This role makes ARA an important dietary component in supportof the muscle anabolic process. One of the lead researchers of the Baylor study (see Bodybuilding section) onarachidonic acid, Mike Roberts MS, CSCS, has authored an article published under the title Arachidonic Acid, TheNew Mass Builder explaining the role of this nutrient in muscle anabolism, and its potential for the enhancement ofmuscle size and strength.[23] The paper explains that for optimal muscle growth, a training stimulus must elicitlocalized inflammation and soreness. It explains that arachidonic acid (AA, 20:4n-6) is an essential omega-6 (1-6)polyunsaturated fatty acid that is abundant in skeletal muscle membrane phospholipids (figure 2). It is also the body'sprincipal building block for the production of prostaglandins, which are known to have various physiological roles,including a close involvement in inflammation. Also, the prostaglandin isomer PGF2a has a potent ability tostimulate muscle growth. As such, arachidonic acid is a regulator of localized muscle inflammation, and may be acentral nutrient controlling the intensity of the anabolic/tissue-rebuilding response to weight training.

BrainArachidonic acid is one of the most abundant fatty acids in the brain, and is present in similar quantities todocosahexaenoic acid (DHA). The two account for approximately 20% of its fatty acid content.[24] Like DHA,neurological health is reliant upon sufficient levels of arachidonic acid. Among other things, arachidonic acid helpsto maintain hippocampal cell membrane fluidity.[25] It also helps protect the brain from oxidative stress by activatingperoxisome proliferator-activated receptor gamma.[26] ARA also activates syntaxin-3 (STX-3), a protein involved inthe growth and repair of neurons.[27]

Arachidonic acid 123

Arachidonic acid is also involved in early neurological development. In one study funded by the U.S. NationalInstitute of Child Health and Human Development, infants (18 months) given supplemental arachidonic acid for 17weeks demonstrated significant improvements in intelligence, as measured by the Mental Development Index.[28]

This effect is further enhanced by the simultaneous supplementation of ARA with DHA.In adults, the disturbed metabolism of ARA may be associated with neurological disorders such as Alzheimer’sdisease and Bipolar disorder.[29] This may involve significant alterations in the conversion of arachidonic acid toother bioactive molecules (overexpression or disturbances in the ARA enzyme cascade). Notably, dietaryarachidonic acid consumption is not associated with the onset of Alzheimer's disease, and studies suggest thesupplementation of arachidonic acid during the early stages of this disease may actually be effective in reducingsymptoms and slowing the disease progress.[30] Additional studies on arachidonic acid supplementation forAlzheimer's patients are needed.

Bodybuilding supplementArachidonic acid is marketed as an anabolic bodybuilding supplement in a variety of products. The first clinicalstudy concerning the use of arachidonic acid as a sport supplement[31] found the following statistically significantimprovement, and statistically strong trends:A significant group × time interaction for relative Wingate peak power was observed among groups (P = 0.02) withgains in peak power being significantly greater in the AA group (0.3 ± 1.2 W·kg-1) vs. PLA (0.2 ± 0.7 W·kg-1,Figure 1). Using repeated measures ANOVA with delta scores, the AA group experienced significantly greaterincreases in comparison to the PLA group at day 50 (P < 0.05). Statistical trends were seen in Wingate total work(AA: 1,292 ± 1,206 vs. PLA: 510 ± 1,249 J, P = 0.09, ηp 2 = 0.052), favoring the AA group.With regard to inflammation, the paper reported a statistically significant reduction in resting IL-6 levels (a centralregulator of inflammation):IL-6 levels experienced a significant group × time interaction (P = 0.04) among groups with subsequent post hocanalyses revealing that IL-6 was significantly lower at day 25 of the study. One-way ANOVA of IL-6 delta values atday 25 revealed significantly greater increases in PLA when compared to AA group (AA: 0.8 ± 13.5 pg·ml-1 vs.PLA: 52.5 ± 1.6 pg·ml-1, P = 0.01; Figure 2)Arachidonic acid was shown to improve peak muscle power, reduce resting IL-6 levels, and produce statisticallystrong trends of improvements in muscle endurance, average power, and bench press 1-rep maximum lift. This studyprovided preliminary evidence supporting the use of arachidonic acid in sports nutrition.

Dietary arachidonic acid and inflammationUnder normal metabolic conditions, the increased consumption of arachidonic acid is unlikely to increaseinflammation. ARA is metabolized to both proinflammatory and anti-inflammatory molecules.[32] Studies givingbetween 840 mg and 2,000 mg per day to healthy individuals for up to 50 days have shown no increases ininflammation or related metabolic activities.[32][33][34][35] Increased arachidonic acid levels are actually associatedwith reduced pro-inflammatory IL-6 and IL-1 levels, and increased anti-inflammatory tumor necrosis factor-beta.[36]

This may result in a reduction in systemic inflammation.Arachidonic acid does still play a central role in inflammation related to injury and many diseased states. How it ismetabolized in the body dictates its inflammatory or anti-inflammatory activity. Individuals suffering from jointpains or active inflammatory disease may find that increased arachidonic acid consumption exacerbates symptoms,presumably because it is being more readily converted to inflammatory compounds. Likewise, high arachidonic acidconsumption is not advised for individuals with a history of inflammatory disease, or who are in compromisedhealth. Of note, while ARA supplementation does not appear to have proinflammatory effects in healthy individuals,it may counter the anti-inflammatory effects of omega-3 fatty acid supplementation.[37]

Arachidonic acid 124

Health effects of arachidonic acid supplementationArachidonic acid supplementation in daily dosages of 1,000–1,500 mg for 50 days has been well tolerated duringseveral clinical studies, with no significant side effects reported. All common markers of health, including kidneyand liver function,[34] serum lipids,[38] immunity,[39] and platelet aggregation[33] appear to be unaffected with thislevel and duration of use. Furthermore, higher concentrations of ARA in muscle tissue may be correlated withimproved insulin sensitivity.[40] Arachidonic acid supplementation of the diets of healthy adults appears to offer notoxicity or significant safety risk.A scientific advisory from the American Heart Association has favorably evaluated the health impact of dietaryomega-6 fats, including arachidonic acid.[41] The group does not recommend limiting this essential fatty acid. In fact,the paper recommends individuals follow a diet that consists of at least 5–10% of calories coming from omega-6fats, including arachidonic acid. Dietary ARA is not a risk factor for heart disease, and may play a role inmaintaining optimal metabolism and reduced heart disease risk. It is, therefore, recommended to maintain sufficientintake levels of both omega-3 and omega-6 essential fatty acids for optimal health.Arachidonic acid is not carcinogenic, and studies show dietary level is not associated (positively or negatively) withrisk of cancers.[42][43][44][45] ARA remains integral to the inflammatory and cell growth process, however, which isdisturbed in many types of disease including cancer. Therefore, the safety of arachidonic acid supplementation inpatients suffering from cancer, inflammatory, or other diseased states is unknown, and supplementation is notrecommended.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=506-32-1[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=444899[3] http:/ / www. chemspider. com/ 392692[4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=27YG812J1I[5] http:/ / esis. jrc. ec. europa. eu/ lib/ einecs_IS_reponse. php?genre=ECNO& entree=208-033-4[6] http:/ / www. drugbank. ca/ drugs/ DB04557[7] http:/ / www. kegg. jp/ entry/ C00219[8] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2007/ MB_cgi?mode=& term=Arachidonic+ acid[9] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=36306[10] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL15594[11] http:/ / www. 3dmet. dna. affrc. go. jp/ html/ B00061. html[12] http:/ / chemapps. stolaf. edu/ jmol/ jmol.

php?model=CCCCC%2FC%3DC%5CC%2FC%3DC%5CC%2FC%3DC%5CC%2FC%3DC%5CCCCC%28%3DO%29O[13] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=457812636& page2=%3AArachidonic+ acid[14] "Dorland's Medical Dictionary – 'A'" (http:/ / www. mercksource. com/ pp/ us/ cns/ cns_hl_dorlands.

jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_a_56zPzhtm). Archived (http:/ / web. archive. org/ web/20070111113516/ http:/ / www. mercksource. com/ pp/ us/ cns/ cns_hl_dorlands.jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_a_56zPzhtm) from the original on 11 January 2007. . Retrieved2007-01-12.

[15] Baynes, John W.; Marek H. Dominiczak (2005). Medical Biochemistry 2nd. Edition. Elsevier Mosby. p. 555. ISBN 0-7234-3341-0.[16] MacDonald, ML; Rogers, QR; Morris, JG (1984). "Nutrition of the Domestic Cat, a Mammalian Carnivore". Annual Review of Nutrition 4:

521–62. doi:10.1146/annurev.nu.04.070184.002513. PMID 6380542.[17] Rivers, JP; Sinclair, AJ; Craqford, MA (1975). "Inability of the cat to desaturate essential fatty acids". Nature 258 (5531): 171–3.

Bibcode 1975Natur.258..171R. doi:10.1038/258171a0. PMID 1186900.[18] History of Martek (http:/ / www. martek. com/ About/ History. aspx), Martek.com[19] Walter F., PhD. Boron (2003). Medical Physiology: A Cellular And Molecular Approaoch. Elsevier/Saunders. p. 108. ISBN 1-4160-2328-3.[20] Walter F., PhD. Boron (2003). Medical Physiology: A Cellular And Molecular Approaoch. Elsevier/Saunders. p. 103. ISBN 1-4160-2328-3.[21] Walter F., PhD. Boron (2003). Medical Physiology: A Cellular And Molecular Approaoch. Elsevier/Saunders. pp. 104.

ISBN 1-4160-2328-3.[22] Trappe, TA; Fluckey, JD; White, F; Lambert, CP; Evans, WJ (2001). "Skeletal muscle PGF(2)(alpha) and PGE(2) in response to eccentric

resistance exercise: influence of ibuprofen acetaminophen.". The Journal of Clinical Endocrinology and Metabolism 86 (10): 5067–70.doi:10.1210/jc.86.10.5067. PMID 11600586.

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[23] http:/ / www. bodybuilding. com/ fun/ llewellyn2. htm[24] Crawford, MA; Sinclair, AJ (1971). "Nutritional influences in the evolution of mammalian brain. In: lipids, malnutrition & the developing

brain". Ciba Foundation symposium: 267–92. PMID 4949878.[25] Fukaya, T.; Gondaira, T.; Kashiyae, Y.; Kotani, S.; Ishikura, Y.; Fujikawa, S.; Kiso, Y.; Sakakibara, M. (2007). "Arachidonic acid preserves

hippocampal neuron membrane fluidity in senescent rats". Neurobiology of Aging 28 (8): 1179–1186.doi:10.1016/j.neurobiolaging.2006.05.023. PMID 16790296.

[26] Wang, ZJ; Liang, CL; Li, GM; Yu, CY; Yin, M (2006). "Neuroprotective effects of arachidonic acid against oxidative stress on rathippocampal slices". Chemico-biological interactions 163 (3): 207–17. doi:10.1016/j.cbi.2006.08.005. PMID 16982041.

[27] Darios, F; Davletov, B (2006). "Omega-3 and omega-6 fatty acids stimulate cell membrane expansion by acting on syntaxin 3.". Nature 440(7085): 813–7. Bibcode 2006Natur.440..813D. doi:10.1038/nature04598. PMID 16598260.

[28] "A randomized controlled trial of early dietary supply of long-chain polyunsaturated fatty acids and mental development in term infants"(http:/ / onlinelibrary. wiley. com/ doi/ 10. 1111/ j. 1469-8749. 2000. tb00066. x/ abstract). . Retrieved July 03, 2012.

[29] Rapoport, SI (2008). "Arachidonic acid and the brain". The Journal of nutrition 138 (12): 2515–20. PMID 19022981.[30] Schaeffer, EL; Forlenza, OV; Gattaz, WF (2009). "Phospholipase A2 activation as a therapeutic approach for cognitive enhancement in

early-stage Alzheimer disease". Psychopharmacology 202 (1–3): 37–51. doi:10.1007/s00213-008-1351-0. PMID 18853146.[31] Roberts, MD; Iosia, M; Kerksick, CM; Taylor, LW; Campbell, B; Wilborn, CD; Harvey, T; Cooke, M et al. (2007). "Effects of arachidonic

acid supplementation on training adaptations in resistance-trained males". Journal of the International Society of Sports Nutrition 4: 21.doi:10.1186/1550-2783-4-21. PMC 2217562. PMID 18045476.

[32] Harris, WS; Mozaffarian, D; Rimm, E; Kris-Etherton, P; Rudel, LL; Appel, LJ; Engler, MM; Engler, MB et al. (2009). "Omega-6 fatty acidsand risk for cardiovascular disease: a science advisory from the American Heart Association Nutrition Subcommittee of the Council onNutrition, Physical Activity, and Metabolism; Council on Cardiovascular Nursing; and Council on Epidemiology and Prevention". Circulation119 (6): 902–7. doi:10.1161/CIRCULATIONAHA.108.191627. PMID 19171857.

[33] Nelson, GJ; Schmidt, PC; Bartolini, G; Kelley, DS; Kyle, D (1997). "The effect of dietary arachidonic acid on platelet function, platelet fattyacid composition, and blood coagulation in humans". Lipids 32 (4): 421–5. doi:10.1007/s11745-997-0055-7. PMID 9113631.

[34] Changes in whole blood and clinical safety markers over 50 days of concomitant arachidonic acid supplementation and resistance training.Wilborn, C, M Roberts, C Kerksick, M Iosia, L Taylor, B Campbell, T Harvey, R Wilson, M. Greenwood, D Willoughby and R Kreider.Proceedings of the International Society of Sports Nutrition (ISSN) Conference June 15–17, 2006. http:/ / arachidonic. com/ARA-baylorsafety. pdf

[35] Pantaleo, P; Marra, F; Vizzutti, F; Spadoni, S; Ciabattoni, G; Galli, C; La Villa, G; Gentilini, P et al. (2004). "Effects of dietarysupplementation with arachidonic acid on platelet and renal function in patients with cirrhosis". Clinical science 106 (1): 27–34.doi:10.1042/CS20030182. PMID 12877651.

[36] Ferrucci, L; Cherubini, A; Bandinelli, S; Bartali, B; Corsi, A; Lauretani, F; Martin, A; Andres-Lacueva, C et al. (2006). "Relationship ofplasma polyunsaturated fatty acids to circulating inflammatory markers". The Journal of Clinical Endocrinology and Metabolism 91 (2):439–46. doi:10.1210/jc.2005-1303. PMID 16234304.

[37] Li, B; Birdwell, C; Whelan, J (1994). "Antithetic relationship of dietary arachidonic acid and eicosapentaenoic acid on eicosanoidproduction in vivo". Journal of lipid research 35 (10): 1869–77. PMID 7852864.

[38] Nelson, GJ; Schmidt, PC; Bartolini, G; Kelley, DS; Phinney, SD; Kyle, D; Silbermann, S; Schaefer, EJ (1997). "The effect of dietaryarachidonic acid on plasma lipoprotein distributions, apoproteins, blood lipid levels, and tissue fatty acid composition in humans". Lipids 32(4): 427–33. doi:10.1007/s11745-997-0056-6. PMID 9113632.

[39] Kelley, DS; Taylor, PC; Nelson, GJ; MacKey, BE (1998). "Arachidonic acid supplementation enhances synthesis of eicosanoids withoutsuppressing immune functions in young healthy men". Lipids 33 (2): 125–30. doi:10.1007/s11745-998-0187-9. PMID 9507233.

[40] Borkman, M; Storlien, LH; Pan, DA; Jenkins, AB; Chisholm, DJ; Campbell, LV (1993). "The relation between insulin sensitivity and thefatty-acid composition of skeletal-muscle phospholipids". The New England Journal of Medicine 328 (4): 238–44.doi:10.1056/NEJM199301283280404. PMID 8418404.

[41] Harris, WS; Mozaffarian, D; Rimm, E; Kris-Etherton, P; Rudel, LL; Appel, LJ; Engler, MM; Engler, MB et al. (2009). "Omega-6 FattyAcids and Risk for Cardiovascular Disease: A Science Advisory From the American Heart Association Nutrition Subcommittee of the Councilon Nutrition, Physical Activity, and Metabolism; Council on Cardiovascular Nursing; and Council on Epidemiology and Prevention".Circulation 119 (6): 902–7. doi:10.1161/CIRCULATIONAHA.108.191627. PMID 19171857.

[42] Schuurman, AG; Van Den Brandt, PA; Dorant, E; Brants, HA; Goldbohm, RA (1999). "Association of energy and fat intake with prostatecarcinoma risk: results from The Netherlands Cohort Study". Cancer 86 (6): 1019–27.doi:10.1002/(SICI)1097-0142(19990915)86:6<1019::AID-CNCR18>3.0.CO;2-H. PMID 10491529.

[43] Leitzmann, MF; Stampfer, MJ; Michaud, DS; Augustsson, K; Colditz, GC; Willett, WC; Giovannucci, EL (2004). "Dietary intake of n-3and n-6 fatty acids and the risk of prostate cancer". The American journal of clinical nutrition 80 (1): 204–16. PMID 15213050.

[44] Astorg, P (2005). "Dietary fatty acids and colorectal and prostate cancers: epidemiological studies". Bulletin du cancer 92 (7): 670–84.PMID 16123006.

[45] Whelan, J; McEntee, MF (2004). "Dietary (n-6) PUFA and intestinal tumorigenesis". The Journal of nutrition 134 (12 Suppl):3421S–3426S. PMID 15570048.

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External links• Arachidonic Acid (http:/ / www. acnp. org/ g4/ GN401000059/ Default. htm) at acnp.org• Arachidonic+Acid (http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2011/ MB_cgi?mode=& term=Arachidonic+ Acid) at

the US National Library of Medicine Medical Subject Headings (MeSH)

alpha-Linolenic acid 127

alpha-Linolenic acid

α-Linolenic acid

Identifiers

CAS number 463-40-1 [1] 

PubChem 5280934 [2]

ChemSpider 4444437 [3] 

UNII 0RBV727H71 [4] 

DrugBank DB00132 [5]

ChEBI CHEBI:27432 [6] 

ChEMBL CHEMBL8739 [7] 

Jmol-3D images Image 1 [8]

Image 2 [9]

Properties

Molecular formula C18H30O2

Molar mass 278.43 g mol−1

  (verify) [10] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

α-Linolenic acid is an organic compound found in many common vegetable oils. In terms of its structure, it isnamed all-cis-9,12,15-octadecatrienoic acid.[11] In physiological literature, it is given the name 18:3 (n−3).α-Linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond islocated at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is apolyunsaturated n−3 (omega-3) fatty acid. It is an isomer of gamma-linolenic acid, a polyunsaturated n−6 (omega-6)fatty acid.

alpha-Linolenic acid 128

HistoryAlpha-linolenic acid was first isolated by Rollett[12] as cited in J. W. McCutcheon's synthesis in 1942,[13] andreferred to in Green and Hilditch's 1930's survey.[14] It was first artificially synthesized in 1995 from C6homologating agents. A Wittig reaction of the phosphonium salt of [(Z-Z)-nona-3,6-dien-1-yl]triphenylphosphoniumbromide with methyl 9-oxononanoate, followed by saponification, completed the synthesis.[15]

Dietary sourcesSeed oils are the richest sources of α-linolenic acid, notably those of rapeseed (canola), soybeans, walnuts, flaxseed(linseed oil), perilla, chia, and hemp. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves ofPisum sativum (pea leaves).[16] The α-linolenic acid itself is suitable for many cooking purposes, at least as much asother minimally suitable cooking oils (such as butter, to which it is thermally superior), as it can withstandtemperatures up to 350 °F (177 degrees Celsius) for 2 hours.[17]

Common name Alternate name Linnaean name % ALA† ref.

Chia chia sage Salvia hispanica 64% [18]

Kiwifruit seeds Chinese gooseberry Actinidia chinensis 62% [18]

Perilla shiso Perilla frutescens 58% [18]

Flax linseed Linum usatissimum 55% [18]

Lingonberry cowberry Vaccinium vitis-idaea 49% [18]

Camelina camelina Camelina sativa 35-45%

Purslane portulaca Portulaca oleracea 35% [18]

Sea buckthorn seaberry Hippophae rhamnoides L. 32% [19]

Hemp cannabis Cannabis sativa 20% [18]

Rapeseed canola Brassica napus 10% [11]

Soybean soya Glycine max 8% [11]

†average val

alpha-Linolenic acid 129

Potential role in nutrition and health

Flax is a rich source ofα-linolenic acid.

α-Linolenic acid, an n−3 fatty acid, is a member of the group of essential fatty acids(EFAs), so called because they cannot be produced within the body and must be acquiredthrough diet. Most seeds and seed oils are much richer in an n−6 fatty acid, linoleic acid.Linoleic acid is also an EFA, but it, and the other n−6 fatty acids, compete with n−3s forpositions in cell membranes and have very different effects on human health. (SeeEssential fatty acid interactions.)

α-Linolenic acid can only be obtained by humans through their diets because the absenceof the required 12- and 15-desaturase enzymes makes de novo synthesis from stearic acidimpossible. Eicosapentaenoic acid (EPA; 20:5, n−3) and docosahexaenoic acid (DHA;22:6, n−3) are readily available from fish and algae oil and play a vital role in manymetabolic processes. These can also be synthesized by humans from dietary α-linolenicacid, but with an efficiency of only a few percent.[20] Because the efficacy of n−3long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascadeof α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even morerestricted than that of EPA.[21][22]

Preliminary research has found evidence that α-linolenic acid is related to a lower risk ofcardiovascular disease.[23][24]

A 2005 study found that daily administration of α-linolenic acid significantly reduced both self-reported anxiety,stress levels, and objective measured cortisol levels in college age students.[25]

A large 2006 study found no association between total α-linolenic acid intake and overall risk of prostate cancer.[26]

Multiple studies[27][28] have shown a relationship between alpha-linolenic acid (ALA), which is abundant in linseedoil, and an increased risk of prostate cancer. This risk was found to be irrespective of source of origin (e.g., meat,vegetable oil).[29] A recent (2009) meta-analysis, however, found evidence of publication bias in earlier studies, andconcluded that if ALA contributes to increased prostate cancer risk, the increase in risk is quite small.[30]

Basic research has also suggested a major neuroprotective effect of α-linolenic acid in in vivo models of both globalischemia and kainate-induced epilepsy;[31] however, if sourced from flax seed oil, residues may have adverse effectdue to its content of neurotoxic cyanogen glycosides and immunosuppressive cyclic nonapeptides.[32]

A 2011 longitudinal study of over 50,000 women, conducted at Harvard University, over a period of ten years, foundthat a higher intake of α-Linolenic acid (combined with a lower intake of linoleic acid) was positively associatedwith a significant reduction in depression in the same group (the same study also found that by contrast an intake ofEPA and DPA found in fish oils did not reduce depression).[33]

Stability and HydrogenationAlpha-linolenic acid is relatively more susceptible to oxidation and will become rancid more quickly than manyother oils. Oxidative instability of α-linolenic acid is one reason why producers choose to partially hydrogenate oilscontaining α-linolenic acid, such as soybean oil.[34] Soybeans are the largest source of edible oils in the U.S., and40% of soy oil production is partially hydrogenated.[35][36]

However, when partially hydrogenated, part of the unsaturated fatty acids become unhealthy trans fats. Consumersare increasingly avoiding products that contain trans fats, and governments have begun to ban trans fats in foodproducts. These regulations and market pressures have spurred the development of low-α-linolenic acid soybeans.These new soybean varieties yield a more stable oil that doesn't require hydrogenation for many applications, thusproviding trans fat-free products, such as frying oil.[37]

alpha-Linolenic acid 130

Several consortia are bringing low-α-linolenic acid soy to market. DuPont's effort involves silencing the FAD2 genethat codes for Δ6-desaturase, giving a soy oil with very low levels of both α-linolenic acid and linoleic acid.[38]

Monsanto Company has introduced to the market Vistive, their brand of low α-linolenic acid soybeans, which is lesscontroversial than GMO offerings, as it was created via conventional breeding techniques.

CardiovascularDietary α-linolenic acid has been assessed for its role in cardiovascular health. Clinical benefits have been seen insome, but not all, studies. Still, a review in 2005 concluded "The weight of the evidence favors recommendations formodest dietary consumption of α-linolenic acid (2 to 3 g per day) for the primary and secondary prevention ofcoronary heart disease."[39]

Drying oilsα-Linolenic acid is the most abundant unsaturated component of several drying oils (e.g. perilla, walnut and linseedoils.)

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=463-40-1[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5280934[3] http:/ / www. chemspider. com/ 4444437[4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=0RBV727H71[5] http:/ / www. drugbank. ca/ drugs/ DB00132[6] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=27432[7] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL8739[8] http:/ / chemapps. stolaf. edu/ jmol/ jmol.

php?model=O%3DC%28O%29CCCCCCC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FCC[9] http:/ / chemapps. stolaf. edu/ jmol/ jmol.

php?model=CC%2FC%3DC%5CC%2FC%3DC%5CC%2FC%3DC%5CCCCCCCCC%28%3DO%29O[10] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=477319349& page2=%3AAlpha-Linolenic+ acid[11] Beare-Rogers (2001). "IUPAC Lexicon of Lipid Nutrition" (http:/ / www. iupac. org/ publications/ pac/ 2001/ pdf/ 7304x0685. pdf) (pdf).

Archived (http:/ / web. archive. org/ web/ 20060212173746/ http:/ / www. iupac. org/ publications/ pac/ 2001/ pdf/ 7304x0685. pdf) from theoriginal on 12 February 2006. . Retrieved 22 February 2006.

[12] Rollett, A. (1909). "Zur kenntnis der linolensäure und des leinöls". Z. Physiol. Chem. 62 (5–6): 422. doi:10.1515/bchm2.1909.62.5-6.422.[13] J. W. McCutcheon (1955), "Linolenic acid" (http:/ / www. orgsyn. org/ orgsyn/ orgsyn/ prepContent. asp?prep=cv3p0531), Org. Synth., ;

Coll. Vol. 3: 351[14] Green, TG; Hilditch, TP (1935). "The identification of linoleic and linolenic acids". Biochem. J. 29 (7): 1552–63. PMC 1266662.

PMID 16745822.[15] Sandri, J.; Viala, J. (1995). "Direct preparation of (Z,Z)-1,4-dienic units with a new C6 homologating agent: synthesis of alpha-linolenic

acid". Synthesis 3 (3): 271–275. doi:10.1055/s-1995-3906.[16] Chapman, David J.; De-Felice, John and Barber, James (May 1983). "Growth temperature effects on thylakoid membrane lipid and protein

content of pea chloroplasts 1". Plant Physiol 72 (1): 225–228. doi:10.1104/pp.72.1.225. PMC 1066200. PMID 16662966.[17] http:/ / www. aaoobfoods. com/ graininfo. htm[18] Seed Oil Fatty Acids – SOFA Database Retrieval (http:/ / www. bagkf. de/ sofa/ )[19] Li, Thomas S. C. (1999). "Sea buckthorn: New crop opportunity" (http:/ / www. hort. purdue. edu/ newcrop/ proceedings1999/ v4-335.

html). Perspectives on new crops and new uses. Alexandria, VA: ASHS Press. pp. 335–337. Archived (http:/ / web. archive. org/ web/20060922084707/ http:/ / www. hort. purdue. edu/ newcrop/ proceedings1999/ v4-335. html) from the original on 22 September 2006. .Retrieved 2006-10-28.

[20] Breanne M Anderson and David WL Ma (2009). "Are all n-3 polyunsaturated fatty acids created equal?". Lipids in Health and Disease 8(33): 33. doi:10.1186/1476-511X-8-33.

[21] Shiels M. Innis (2007). "Fatty acids and early human development". Early Human Development 83 (12): 761–766.doi:10.1016/j.earlhumdev.2007.09.004. PMID 17920214.

[22] Burdge, GC; Calder, PC (2005). "Conversion of alpha-linolenic acid to longer-chain polyunsaturated fatty acids in human adults".Reproduction, nutrition, development 45 (5): 581–97. doi:10.1051/rnd:2005047. PMID 16188209.

[23] Penny M. Kris-Etherton, William S. Harris, [and] Lawrence J. Appel, for the Nutrition Committee (2002). "Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease". Circulation 106 (21): 2747–2757. doi:10.1161/01.CIR.0000038493.65177.94.

alpha-Linolenic acid 131

PMID 12438303.[24] William E. Connor (2000). "Importance of n−3 fatty acids in health and disease". American Journal of Clinical Nutrition 71 (1 Suppl.):

171S–175S. PMID 10617967.[25] Yehuda S., Rabinovitz S., Mostofsky D.I. (2005). "Mixture of essential fatty acids lowers test anxiety". Nutritional Neuroscience 8 (4):

265–267. doi:10.1080/10284150500445795. PMID 16491653.[26] Koralek DO, Peters U, Andriole G, et al. (2006). "A prospective study of dietary α-linolenic acid and the risk of prostate cancer (United

States)". Cancer Causes Control 17 (6): 783–791. doi:10.1007/s10552-006-0014-x. PMID 16783606.[27] Ramon, JM; Bou, R; Romea, S; Alkiza, ME; Jacas, M; Ribes, J; Oromi, J (2000). "Dietary fat intake and prostate cancer risk: a case-control

study in Spain". Cancer causes & control : CCC 11 (8): 679–85. doi:10.1023/A:1008924116552. PMID 11065004.[28] Brouwer, IA; Katan, MB; Zock, PL (2004). "Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but

increased prostate cancer risk: a meta-analysis". The Journal of nutrition 134 (4): 919–22. PMID 15051847.[29] De Stéfani, E; Deneo-Pellegrini, H; Boffetta, P; Ronco, A; Mendilaharsu, M (2000). "Alpha-linolenic acid and risk of prostate cancer: a

case-control study in Uruguay". Cancer Epidemiology, Biomarkers & Prevention 9 (3): 335–8. PMID 10750674.[30] Simon, JA; Chen, YH; Bent, S (2009). "The relation of alpha-linolenic acid to the risk of prostate cancer". American Journal of Clinical

Nutrition 89 (5): 1558S–1564S. doi:10.3945/ajcn.2009.26736E. PMID 19321563.[31] Inger Lauritzen, Nicolas Blondeau, Catherine Heurteaux, Catherine Widmann, Georges Romey and Michel Lazdunski (2000).

"Polyunsaturated fatty acids are potent neuroprotectors". The EMBO Journal 19 (8): 1784–1793. doi:10.1093/emboj/19.8.1784. PMC 302016.PMID 10775263.

[32] (http:/ / worldwide. espacenet. com/ textdoc?DB=EPODOC& IDX=), "WO 2006137717 Edible flaxseed oil which saturated fatty acid andtoxic components were removed therefrom and preparative process thereof"

[33] M. Lucas, F. Mirzaei, E. J. O'Reilly, A. Pan, W. C. Willett, I. Kawachi, K. Koenen, and A. Ascherio (2011). "Dietary intake of n-3 and n-6fatty acids and the risk of clinical depression in women: a 10-y prospective follow-up study". Am J Clin Nutr 93 (6): 1337–43.doi:10.3945/ajcn.111.011817. PMC 3095504. PMID 21471279.

[34] Kinney, Tony. "Metabolism in plants to produce healthier food oils (slide #4)" (http:/ / www. metabolicengineering. gov/ me2005/ Kinney.pdf) (PDF). . Retrieved 2007-01-11.

[35] Fitzgerald, Anne and Brasher, Philip. "Ban on trans fat could benefit Iowa" (http:/ / www. truthabouttrade. org/ article. asp?id=6669). TruthAbout Trade and Technology. . Retrieved 2007-01-03.

[36] Kinney, Tony. "Metabolism in plants to produce healthier food oils (slide #2)" (http:/ / www. metabolicengineering. gov/ me2005/ Kinney.pdf) (PDF). . Retrieved 2007-01-11.

[37] Monsanto. "ADM to process Monsanto's Vistive low linolenic soybeans at Indiana facility" (http:/ / web. archive. org/ web/20061211071206/ http:/ / www. monsanto. com/ monsanto/ layout/ media/ 06/ 01-12-06. asp). Archived from the original (http:/ / www.monsanto. com/ monsanto/ layout/ media/ 06/ 01-12-06. asp) on 2006-12-11. . Retrieved 2007-01-06.

[38] Kinney, Tony. "Metabolism in plants to produce healthier food oils" (http:/ / www. metabolicengineering. gov/ me2005/ Kinney. pdf)(PDF). . Retrieved 2007-01-11.

[39] Mozaffarian D (2005). "Does α-linolenic acid intake reduce the risk of coronary heart disease? A review of the evidence". Alternativetherapies in health and medicine 11 (3): 24–30; quiz 31, 79. PMID 15945135.

Eicosapentaenoic acid 132

Eicosapentaenoic acid

Eicosapentaenoic acid

Identifiers

CAS number 10417-94-4 [1] 

ChemSpider 393682 [2] 

UNII AAN7QOV9EA [3] 

DrugBank DB00159 [4]

ChEBI CHEBI:28364 [5] 

ChEMBL CHEMBL460026 [6] 

Jmol-3D images Image 1 [7]

Properties

Molecular formula C20H30O2

Molar mass 302.451 g/mol

  (verify) [8] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an omega-3 fatty acid. In physiological literature, it isgiven the name 20:5(n-3). It also has the trivial name timnodonic acid. In chemical structure, EPA is a carboxylicacid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from theomega end.

EPA and its metabolites act in the body largely by their interactions with the metabolites of arachidonic acid;see Essential fatty acid interactions for detail.

EPA is a polyunsaturated fatty acid (PUFA) that acts as a precursor for prostaglandin-3 (which inhibits plateletaggregation), thromboxane-3, and leukotriene-5 groups (all eicosanoids).

Eicosapentaenoic acid 133

SourcesIt is obtained in the human diet by eating oily fish or fish oil— e.g., cod liver, herring, mackerel, salmon, menhadenand sardine, and various types of edible seaweed. It is also found in human breast milk.However, fish do not naturally produce EPA, but obtain it from the algae they consume.[9] It is available to humansfrom some non-animal sources (e.g., commercially, from microalgae). Microalgae are being developed as acommercial source.[10] EPA is not usually found in higher plants, but it has been reported in trace amounts inpurslane.[11]

The human body converts alpha-linolenic acid (ALA) to EPA. ALA is itself an essential fatty acid, an appropriatesupply of which must be ensured. The efficiency of the conversion of ALA to EPA, however, is much lower than theabsorption of EPA from food containing it. Because EPA is also a precursor to docosahexaenoic acid (DHA),ensuring a sufficient level of EPA on a diet containing neither EPA nor DHA is harder both because of the extrametabolic work required to synthesize EPA and because of the use of EPA to metabolize DHA. Medical conditionslike diabetes or certain allergies may significantly limit the human body's capacity for metabolization of EPA fromALA.[12]

Clinical significance

Salmon is a rich source of EPA.

The US National Institute of Health's MedlinePlus listsmedical conditions for which EPA (alone or in concertwith other ω-3 sources) is known or thought to be aneffective treatment.[13] Most of these involve its abilityto lower inflammation.

Among omega-3 fatty acids, it is thought that EPA inparticular may possess some beneficial potential inmental conditions, such as schizophrenia.[14][15]

Several studies report an additional reduction in scores on symptom scales used to assess the severity of symptoms,when additional EPA is taken.

Studies published around 2004 have suggested that EPA may decrease depression and, importantly, suicidalbehavior. One such study,[16] took blood samples of 100 suicide attempt patients and compared the blood samples tothose of controls and found that levels of eicosapentaenoic acid were significantly lower in the washed red bloodcells of the suicide-attempt patients. A 2009 metastudy found that patients taking omega-3 supplements with a higherEPA:DHA ratio experienced less depressive symptoms. [17]

EPA has inhibitory effect on CYP2C9 and CYP2C19 hepatic enzymes. At high dose, it may also inhibit the activityof CYP2D6 and CYP3A4, important enzymes involved in drug metabolism.[18]

Research suggests that EPA improves the response of patients to chemotherapy, possibly by modulating theproduction of eicosanoid.[19]

In a study published in 2011, EPA was shown to be significantly more effective than placebo for treatinghyperactivity and attention symptoms, both together and separately.[20]

Eicosapentaenoic acid 134

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=10417-94-4[2] http:/ / www. chemspider. com/ 393682[3] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=AAN7QOV9EA[4] http:/ / www. drugbank. ca/ drugs/ DB00159[5] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28364[6] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL460026[7] http:/ / chemapps. stolaf. edu/ jmol/ jmol.

php?model=O%3DC%28O%29CCC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FCC[8] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443719931& page2=%3AEicosapentaenoic+ acid[9] Yvonne Bishop-Weston. "Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA &

Essential Fats" (http:/ / www. vegetarian-dha-epa. co. uk/ ). . Retrieved 2008-08-05.[10] Jess Halliday (12/01/2007). "Water 4 to introduce algae DHA/EPA as food ingredient" (http:/ / www. nutraingredients. com/ news/ ng.

asp?n=73324-water-omega-algae). . Retrieved 2007-02-09.[11] Simopoulos, Artemis P (2002). "Omega-3 fatty acids in wild plants, nuts and seeds" (http:/ / apjcn. nhri. org. tw/ server/ APJCN/ Volume11/

vol11sup2/ S163. pdf). Asia Pacific Journal of Clinical Nutrition 11 (Suppl 2): S163–73. doi:10.1046/j.1440-6047.11.s.6.5.x. .[12] Plant based sources of vegan & Vegetarian DHA & EPA and Omega 3 essential fatty acids (http:/ / www. foodsforlife. org. uk/ nutrition/

vegetarian-DHA-EPA. html)[13] NIH Medline Plus. "MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid" (http:/ / www. nlm. nih. gov/

medlineplus/ druginfo/ natural/ patient-fishoil. html). . Retrieved February 14, 2006.[14] Peet M, Brind J, Ramchand CN, Shah S, Vankar GK (2001). "Two double-blind placebo-controlled pilot studies of eicosapentaenoic acid in

the treatment of schizophrenia" (http:/ / jerrycott. com/ user/ peet. pdf). Schizophrenia Research 49 (3): 243–51.doi:10.1016/S0920-9964(00)00083-9. PMID 11356585. .

[15] Song C, Zhao S (Oct 2007). "Omega-3 fatty acid eicosapentaenoic acid. A new treatment for psychiatric and neurodegenerative diseases: areview of clinical investigations". Expert Opin Investig Drugs 16 (10): 1627–38. doi:10.1517/13543784.16.10.1627. PMID 17922626.

[16] Huan M, Hamazaki K, Sun Y, Itomura M, Liu H, Kang W, Watanabe S, Terasawa K, Hamazaki T. (2004). "Suicide attempt and n-3 fattyacid levels in red blood cells: a case control study in China" (http:/ / www. journals. elsevierhealth. com/ periodicals/ bps/ article/PIIS0006322304007061/ abstract) (abstract). Biological Psychiatry 56 (7): 490–6. doi:10.1016/j.biopsych.2004.06.028. PMID 15450784. .

[17] http:/ / www. jacn. org/ content/ 28/ 5/ 525. full[18] Yao HT, Chang YW, Lan SJ, Chen CT, Hsu JT, Yeh TK (2006). "The inhibitory effect of polyunsaturated fatty acids on human CYP

enzymes". Life Sci. 79 (26): 2432–40. doi:10.1016/j.lfs.2006.08.016. PMID 16978661.[19] Hardman,W Elaine (2004). "(n-3)Fatty Acids and Cancer Therapy" (http:/ / jn. nutrition. org/ cgi/ content/ full/ 134/ 12/ 3427S). Journal of

Nutrition 134 (12): 3427S. PMID 15570049. .[20][20] Journal of American Academy of Child and Adolescent Psychiatry 2011 Oct; 50:991

Erucic acid 135

Erucic acid

Erucic acid

Identifiers

CAS number 112-86-7 [1] 

PubChem 5281116 [2]

ChemSpider 4444561 [3] 

UNII 075441GMF2 [4] 

KEGG C08316 [5] 

ChEBI CHEBI:28792 [6] 

ChEMBL CHEMBL1173380 [7] 

Jmol-3D images Image 1 [8]

Properties

Molecular formula C22H42O2

Molar mass 338.57 g mol−1

Appearance White waxy solid

Density 0.860 g/cm3

Melting point 33.8 °C, 307 K, 93 °F

Boiling point 381.5 °C (decomposes)

Solubility in water Insoluble

Solubility in methanol and ethanol Soluble

Hazards

Flash point 349.9 °C (661.8 °F)

  (verify) [9] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the formulaCH3(CH2)7CH=CH(CH2)11COOH. It is prevalent in wallflower seed, makes up 4.1% of rapeseed oil[10], and makesup 42% of mustard oil. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known asbrassidic acid.

Erucic acid 136

UsesErucic acid has many of the same uses as mineral oils, but it is more readily biodegradable than some. It has limitedability to polymerize and dry for use in oil paints. Like other fatty acids, it can be converted into surfactants,lubricant and is a precursor to bio-diesel.Derivatives of erucic acid have many further uses, such as behenyl alcohol (CH3(CH2)21OH), a pour pointdepressant (enabling liquids to flow at a lower temperature), and silver behenate, for use in photography.[11] It is alsoused as an ingredient in appetite suppressants.

Sources of erucic acid

The seed oil of the rape plant is rich in erucic acid.

The name erucic means: of or pertaining to eruca;which is a genus of flowering plants in the familyBrassicaceae. It is also the Latin for coleworth, whichtoday is better known as kale.

Erucic acid is produced naturally (together with otherfatty acids) across a great range of green plants, butespecially so in members of the brassica family. It ishighest in some of the rapeseed varieties of brassicas,kale and mustard being some of the highest, followedby Brussels spouts and broccoli.[12] For industrialpurposes, a Low-Erucic Acid Rapeseed (LEAR) hasbeen developed, which contains fats derived from oleicacid instead of erucic acid.[13]

BiochemistryErucic acid is produced by elongation of oleic acid via oleoyl-coenzyme A and malonyl-CoA.[12] Erucic acid isbroken down into shorter-chain fatty acids in the human liver by the long-chain Acyl CoA dehydrogenase enzyme.

Health effectsThe effects of erucic acid from edible oils on human health are controversial. However no negative health effectshave ever been documented in humans.[14]

Mustard oil was once considered unsuitable for human consumption in the United States, Canada, and the EuropeanUnion due to the high content of erucic acid. This is because of early studies in rats. Subsequent studies on rats haveshown that they are less able to digest vegetable fats (whether they contain erucic acid or not) than humans andpigs.[15][16][17] Chariton et al. suggests that in rats: “Inefficient activation of erucic acid to erucyl-CoA and a lowlevel of activity of triglyceride lipase and enzymes of betaoxidation for erucic acid probably contribute to theaccumulation and retention of cardiac lipid.”[18] Before this process was fully understood it led to the belief thaterucic acid and mustard oil were both highly toxic to humans.Epidemiological studies suggest that, in regions where mustard oil is still used in a traditional manner, mustard oil may afford some protection against cardiovascular diseases. In this sense “traditional” means that (a) the oil is used fresh; and (b) vegetable fats count only as a small percentage of the total caloric intake. Whether this effect is due to the nature of erucic acid per se to make the blood platelets less sticky, or to the presence of a reasonably high percentage of α-linolenic acid, or to a combination of properties of fresh unrefined oil, is as yet uncertain. Care needs to be taken with such epidemiological studies to exclude the possibility of early deaths from other causes skewing

Erucic acid 137

the results. The fact that early asymptomatic coronary disease is readily detectable post mortem and is absent in themustard oil cohorts tends to add weight to the hypothesis that mustard oil is protective.[19]

A four-to-one mixture of erucic acid and oleic acid constitutes Lorenzo's oil; an experimental treatment for the rareneurobiology disorder adrenoleukodystrophy. Thrombocytopenia has been seen in patients treated with Lorenzo’soil, probably related to its erucic acid content.[20] For the reasons given above, it is not advisable for nursing mothersor babies to eat food containing erucic acid.[14][21]

The high percentage of erucic acid in mustard oil has led to the latter being banned for food use in the EuropeanUnion and other countries.

Health concernsBefore genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil fromrapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it waspossible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would getstripped out of the genome as well, greatly reducing its valuable erucic acid content. Studies on rats show lipidosisproblems when fed high quantities of erucic acid, however, so this did not hinder saleability.[18] Later trials showedthat rats had the same problems with other vegetable fatty acids,[22] because rats are poor at metabolising somefats.[23] The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that ofits competitors.There are not many studies done on humans with erucic acid; the majority are carried out by the food scienceindustry on animals. Animal studies failed to show negative events occurring from feeding of erucic acid, and thestudies were repeated under increasingly unnatural scenarios. In one case, neonate piglets that have a limited abilityto absorb these fats had their normal sow's milk replaced solely with rapeseed oil for one hundred percent of theircalorific needs.[23] The studies showed that lipidoses suffered by the piglets proved to be only a transient effect; theliver automatically responded by increasing enzyme levels to cope with the unusual diet, and the lipidoses subsided.A recent study recorded the higher rates of lung cancer in countries with populations that cook over solid fuel woodand biomass fires and stoves. The possibility of production of smoke from heated oil was also considered, and it wasestablished that rapeseed oil, which contains erucic acid, can cause increased lung carcinomas through emissionsunder high heat. However, the report also showed a variety of cooking oils also did this at similar heats.[24]

Cardiac concernsThe levels of erucic acid in human foods are restricted, in part, over concerns that it may adversely affect hearttissue.[14] However, these concerns seem to have been premature: an early study had shown rapeseed oil, whichcontains erucic acid, promoted myocardial lesions in male adult rat animal models; but later studies revealed similareffects from other oils, containing no erucic acid [25]; also, the same effects were not observed in female adultrats.[23] [26] Choline and inositol offered some protection against this damage,[26] while alpha-linolenic acid mayhave aggravated it.[27] Erucic acid is preferentially absorbed in myocardium tissue[28] but is not metabolizedthere.[23]

As the above studies demonstrate, rats present a poor animal model to study the effects of erucic acid on human hearttissue due to their own poor ability to metabolize this fat.

Erucic acid 138

Low erucic acid rapeseedBefore the advent of genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purposecrop from oil-rapeseed that would appeal to a larger market by making it more palatable and safer for cattle and otherlivestock. While it was possible to breed out much of the pungent-tasting glucosinolates that were the cause of theproblem, the traditional methods of plant breeding resulted in one of the dominant erucic acid genes also gettingstripped out of the genome in the process, thus greatly reducing its erucic acid content. Although this latter effectwas an unintended consequence of the breeding program, it was noticed from studies on rats that they show signs oflipidosis when fed high quantities of erucic acid.[18]

Food grade rapeseed oil (also known as canola oil, rapeseed 00 oil, low erucic acid rapeseed oil, LEAR oil, andrapeseed canola-equivalent oil) is regulated to a maximum of 2% erucic acid by weight in the USA.[29] and 5% in theEU,[30] with special regulations for infant food.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=112-86-7[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5281116[3] http:/ / www. chemspider. com/ 4444561[4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=075441GMF2[5] http:/ / www. kegg. jp/ entry/ C08316[6] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28792[7] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL1173380[8] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCC%5CC%3DC%2FCCCCCCCC[9] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443733783& page2=%3AErucic+ acid[10] Sahasrabudhe, M. R. (1977). "Crismer values and erucic acid contents of rapeseed oils". Journal of the American Oil Chemists' Society 54

(8): 323–324. doi:10.1007/BF02672436.[11] Economic Research Service, USDA (1996). "Crambe, Industrial Rapeseed, and Tung Provide Valuable Oils" (http:/ / www. ers. usda. gov/

publications/ IUS6/ ius6c. pdf) (pdf). Fats and Oils, Industrial Uses: 18. .[12] Bao Xiaoming, Pollard Mike, Ohlrogge John (1998). "The Biosynthesis of Erucic Acid in Developing Embryos of Brassica rapa". Plant

Physiol 118: 183–190. PMID 9733537.[13][13] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[14] Food Standards Australia New Zealand (June 2003) Erucic acid in food (http:/ / www. foodstandards. gov. au/ _srcfiles/ Erucic acid

monograph. pdf) : A Toxicological Review and Risk Assessment . Technical report series No. 21; Page 4 paragraph 1; ISBN 0-642-34526-0,ISSN 1448-3017

[15] Hulan HW, Kramer JK, Mahadevan S, Sauer FD (January 1976). "Relationship between erucic acid and myocardial changes in male rats".Lipids 11 (1): 9–15. doi:10.1007/BF02532578. PMID 1250074.

[16] Kramer JK, Farnworth ER, Thompson BK, Corner AH, Trenholm HL (May 1982). "Reduction of myocardial necrosis in male albino rats bymanipulation of dietary fatty acid levels". Lipids 17 (5): 372–82. doi:10.1007/BF02535197. PMID 7098776.

[17] de Wildt DJ, Speijers GJ (June 1984). "Influence of dietary rapeseed oil and erucic acid upon myocardial performance and hemodynamics inrats" (http:/ / linkinghub. elsevier. com/ retrieve/ pii/ 0041-008X(84)90275-8). Toxicol. Appl. Pharmacol. 74 (1): 99–108.doi:10.1016/0041-008X(84)90275-8. PMID 6729825. .

[18] Charlton KM, Corner AH, Davey K, Kramer JK, Mahadevan S, Sauer FD (July 1975). "Cardiac lesions in rats fed rapeseed oils". Can. J.Comp. Med. 39 (3): 261–9. PMC 1277456. PMID 1170010.

[19] Rastogi T, Reddy KS, Vaz M, et al. (April 2004). "Diet and risk of ischemic heart disease in India" (http:/ / www. ajcn. org/ cgi/ content/full/ 79/ 4/ 582). Am. J. Clin. Nutr. 79 (4): 582–92. PMID 15051601. .

[20] Crowther MA, Barr RD, Kelton J, Whelan D, Greenwald M (February 1995). "Profound thrombocytopenia complicating dietary erucic acidtherapy for adrenoleukodystrophy". American Journal of Hematology 48 (2): 132–3. PMID 7847331.

[21] "Food Standards Agency - Agency issues warning on erucic acid" (http:/ / www. food. gov. uk/ news/ newsarchive/ 2004/ sep/ erucic). 2September 2004. . Retrieved 2007-11-02.

[22] Neat CE, Thomassen MS, Osmundsen H (April 1981). "Effects of high-fat diets on hepatic fatty acid oxidation in the rat. Isolation of ratliver peroxisomes by vertical-rotor centrifugation by using a self-generated, iso-osmotic, Percoll gradient". Biochem. J. 196 (1): 149–59.PMC 1162977. PMID 6272750.

[23] Kramer JK, Hulan HW, Trenholm HL, Corner AH (February 1979). "Growth, lipid metabolism and pathology of two strains of rats fed highfat diets" (http:/ / jn. nutrition. org/ cgi/ pmidlookup?view=long& pmid=430222). J. Nutr. 109 (2): 202–13. PMID 430222. .

Erucic acid 139

[24] S Kurt, Baan R, Grosse Y, Secretan B, (2006) Carcinogenicity of household solid fuel combustion and of high-temperature frying (http:/ /ehs. sph. berkeley. edu/ krsmith/ publications/ 2006 pubs/ Lancet-Oncology3. pdf). WHO International Agency for Research on CancerMonograph Working Group. PDF 52kb. Retrieved 2007-01-29

[25] http:/ / www. foodstandards. gov. au/ _srcfiles/ Erucic%20acid%20monograph. pdf[26] Clandinin MT, Yamashiro S (1982). "Dietary factors affecting the incidence of dietary fat-induced myocardial lesions". J. Nutr. 112 (4):

825–8. PMID 7200131.[27] McCutcheon JS, Umermura T, Bhatnager MK, Walker BL (1976). "Cardiopathogenicity of rapeseed oils and oil blends differing in erucic,

linoleic, and linolenic acid content". Lipids 11 (7): 545–52. doi:10.1007/BF02532900. PMID 948250.[28] Becker W, Bruce A (1985). "Autoradiographic studies with fatty acids and some other lipids: a review". Prog. Lipid Res. 24 (4): 325–46.

doi:10.1016/0163-7827(85)90010-4. PMID 3916594.[29] U.S. Dept. of Health and Human Services (April 1, 2010). "CFR - Code of Federal Regulations Title 21" (http:/ / www. accessdata. fda. gov/

scripts/ cdrh/ cfdocs/ cfcfr/ CFRSearch. cfm?fr=184. 1555). .[30] The Commission of the European Communities (1980-09-27). "Commission Directive 80/891/EEC of 25 July 1980 relating to the

Community method of analysis for determining the erucic acid content in oils and fats intended to be used as such for human consumption andfoodstuffs containing added oils or fats" (http:/ / eur-lex. europa. eu/ LexUriServ/ LexUriServ. do?uri=CELEX:31980L0891:EN:HTML).EurLex Official Journal 254: 35–41. .

Docosahexaenoic acid 140

Docosahexaenoic acid

Docosahexaenoic acid

Identifiers

CAS number 6217-54-5 [1] 

PubChem 445580 [2]

ChemSpider 393183 [3] 

UNII ZAD9OKH9JC [4] 

ChEBI CHEBI:28125 [5] 

ChEMBL CHEMBL367149 [6] 

Jmol-3D images Image 1 [7]

Properties

Molecular formula C22H32O2

Molar mass 328.488 g/mol

Density 0.943 g/cm3

Melting point -44 °C, 229 K, -47 °F

Boiling point 446.7 °C, 720 K, 836 °F

  (verify) [8] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human braincerebral cortex, sperm, testicles and retina. It can be synthesized from alpha-linolenic acid or obtained directly frommaternal milk or fish oil.[9] DHA's structure is a carboxylic acid(~oic acid) with a 22-carbon chain (docosa- is Greekfor 22) and six (Greek "hexa") cis double bonds (-en~);[10] the first double bond is located at the third carbon fromthe omega end.[11] Its trivial name is cervonic acid, its systematic name isall-cis-docosa-4,7,10,13,16,19-hexa-enoic acid, and its shorthand name is 22:6(n-3) in the nomenclature of fattyacids.Cold-water oceanic fish oils are rich in DHA. Most of the DHA in fish and multi-cellular organisms with access to cold-water oceanic foods originates from photosynthetic and heterotrophic microalgae, and becomes increasingly concentrated in organisms the further they are up the food chain. DHA is also commercially manufactured from microalgae; Crypthecodinium cohnii and another of the genus Schizochytrium.[12] DHA manufactured using microalgae is vegetarian.[12] Some animals with access to seafood make very little DHA through metabolism, but

Docosahexaenoic acid 141

obtain it in the diet. However, in strict herbivores, and carnivores that do not eat seafood, DHA is manufacturedinternally from α-linolenic acid, a shorter omega-3 fatty acid manufactured by plants (and also occurring in animalproducts as obtained from plants). Eicosapentaenoic and docosapentaenoic acids are the principal products ofα-linolenic acid metabolism in young men[13] and illustrates the importance of DHA production for the developingfetus and healthy breast milk.[14] Giltay, Gooren, Toorians, and Katan (2004) found rates of conversion 15% higherfor women, and that those taking oral contraceptives demonstrated 10% higher DHA levels.[15] Administration oftestosterone or the aromatase inhibitor anastrozole, which blocks conversion of testosterone to estradiol, reducesDHA conversion.[15] DHA is a major fatty acid in sperm and brain phospholipids and in the retina. Dietary DHAmay reduce the risk of heart disease by reducing the level of blood triglycerides in humans.[16] Below-normal levelsof DHA have been associated with Alzheimer's disease. A low level of DHA is also spotted in patients with retinitispigmentosa.

Central nervous system constituentDHA is the most abundant omega-3 fatty acid in the brain and retina. DHA comprises 40% of the polyunsaturatedfatty acids (PUFAs) in the brain and 60% of the PUFAs in the retina. Fifty percent of the weight of a neuron's plasmamembrane is composed of DHA.[17] DHA is richly supplied during breastfeeding, and DHA levels are high inbreastmilk regardless of dietary choices.DHA modulates the carrier-mediated transport of choline, glycine, and taurine, the function of delayed rectifierpotassium channels, and the response of rhodopsin contained in the synaptic vesicles, among many otherfunctions.[18]

DHA deficiency is associated with cognitive decline.[19] Phosphatidylserine (PS) controls apoptosis, and low DHAlevels lower neural cell PS and increase neural cell death.[20] DHA are reduced in the brain tissue of severelydepressed patients.[21][22]

Metabolic synthesisIn humans, DHA is either obtained from the diet or synthesized from eicosapentaenoic acid (EPA, 20:5, ω-3) viadocosapentaenoic acid (DPA, 22:5 ω-3) as an intermediate. This synthesis had been thought to occur through anelongation step followed by the action of Δ4-desaturase. It is now considered more likely that DHA is biosynthesizedvia a C24 intermediate followed by beta oxidation in peroxisomes. Thus, EPA is twice elongated, yielding 24:5 ω-3,then desaturated to 24:6 ω-3, then shortened to DHA (22:6 ω-3) via beta oxidation. This pathway is known asSprecher's shunt.[23][24]

Health

Attention deficit hyperactivity disorder (ADHD)Research on DHA supplementation and attention deficit hyperactivity disorder (ADHD) have shown mixed results.One study of pure DHA supplementation on children with ADHD found no behavioral improvements,[25] whileanother study found fish oil containing both EPA and DHA did improve behavior,[26] though these studies and mostothers regarding the influence of DHA on behavior are confounded by not controlling for gender differences.[27]

Alzheimer's disease and decline of mental healthPreliminary studies indicated that DHA can slow the progression of Alzhiemer's disease in mice,[28][29] sparkinginterest in additional research. However, the first large-scale human trials showed that DHA did not slow decline ofmental function in elderly people with mild to moderate Alzheimer's disease.[30] These trials were part of a large USNational Institutes of Health (NIH) intervention study to evaluate DHA in Alzheimer's disease.[31]

Docosahexaenoic acid 142

Researchers from the National Institute on Aging-supported Alzheimer's Disease Cooperative Study conducted adouble-blind, randomized, placebo-controlled clinical trial comparing DHA and placebo over 18 months in 402people (average age=76) diagnosed with mild to moderate Alzheimer's at 51 sites. According to this study, treatmentwith DHA increased blood levels of DHA, and appeared to increase brain DHA levels, based on a measured increaseof DHA in study participants' cerebrospinal fluid.However, DHA treatment did not slow the rate of change on tests of mental function, global dementia severity status,activities of daily living, or behavioral symptoms in the study population as a whole. Treatment effects did not differbetween the mild and moderate Alzheimer's patients, leading study authors to conclude that the results do notsupport the routine use of DHA for patients with Alzheimer's.Animal studies in the TG3 transgenic mouse model of Alzheimer's disease had linked dietary DHA to decreases inamyloid plaques and tau. Animal studies also showed, when DHA was combined with arachidonic acid (also presentin fish oil), plaque formation was greater with the arachidonic acid compared to DHA alone.DHA deficiency likely plays a role in decline of mental function in healthy adults, which is indicated in a study from2010 conducted at 19 U.S. clinical sites on 485 subjects aged 55 and older who met criteria for age-associatedmemory impairment. The study found algal DHA taken for six months decreased heart rate and improved memoryand learning in healthy, older adults with mild memory complaints. These findings indicate the importance of earlyDHA intervention and provided a statistically significant benefit to cognitive function in individuals over 50 years ofage.[32] Higher DHA levels in middle-aged adults is related to better performance on tests of nonverbal reasoningand mental flexibility, working memory, and vocabulary.[33]

CancerDHA was found to inhibit growth of human colon carcinoma cells,[34][35] more than other omega-3 PUFAs. Thecytotoxic effect of DHA was not caused by increased lipid peroxidation or any other oxidative damage, but rather adecrease in cell growth regulators. However, different cancer lines handle PUFAs differently and display differentsensitivities toward them. Such preliminary findings point to the need for further research, and are not proof DHAdoes or does not provide any benefit for intended treatment, cure, or mitigation of cancer. However, in 2008, DHAwas shown to increase the efficacy of chemotherapy in prostate cancer cells,[36] and in 2009, a chemoprotectiveeffect in a mouse model was reported.[37] One large clinical trial, the "Prostate Cancer Prevention Trial", found thatDHA was correlated with an increase in high-grade prostate cancer.[38]

Pregnancy and lactationDHA concentrations in breast milk range from 0.07% to greater than 1.0% of total fatty acids, with a mean of about0.34%. DHA levels in breast milk are higher if a mother's diet is high in fish. The Food and Drug Administration hasnoted specific concerns for women who are pregnant or might become pregnant, nursing mothers, and youngchildren regarding mercury levels in fish and shellfish.[39]

DHA has recently gained attention as a supplement for pregnant women, noting studies of improved attention andvisual acuity. Given the recently gained attention, the majority of pregnant women in the U.S. fail to get therecommended amount of DHA in their diets.[40] A working group from the International Society for the Study ofFatty Acids and Lipids recommended 300 mg/day of DHA for pregnant and lactating women, whereas the averageconsumption was between 45 mg and 115 mg per day of the women in the study. The March of Dimes recommendspregnant women consume at least 200 mg DHA per day.[41] Other requirements are available from other sources.[42]

Docosahexaenoic acid single-cell oil (DHASCO)[43][44] has been an ingredient in several brands of premium infant formula sold in North America since 2001 after Mead Johnson, the first infant formula manufacturer to add DHASCO and arachidonic acid single-cell organism oil to its Enfamil Lipil product, received a "Generally Regarded As Safe" status by the Food and Drug Administration and Health Canada. Several past and recent studies indicate supplementation with arachidonic acid (omega-6) may be unsuitable for some infants and toddlers as it may

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potentiate the inflammatory response.[45]

DHASCO does not make infant formulas more like human milk than "conventional" formula containingalpha-linolenic acid and linoleic acid, which are precursors to DHA. Formula sold in North America uses lipids frommicroorganisms grown in bioreactors as sources of DHA.[12][46] No scientific review studies show DHA additivesbenefit brain development of term infants, as formula makers claim in their advertisements, which has led somepublic interest groups to file complaints with the Federal Trade Commission of the United States, alleging false andmisleading advertising.[47]

A study[48] found that preterm infants fed baby formulas fortified with DHASCO provided better developmentaloutcomes than formulas not containing the supplement.A study sponsored by March of Dimes and National Institutes of Health suggests that women who take DHAsupplements during pregnancy give their babies some degree of added protection against getting common colds.[49]

The babies whose mothers had taken DHA supplements seemed to get over cold symptoms faster when they did getsick.

Current researchAlthough most studies demonstrate positive effects of dietary DHA on human health, contrary results exist. Forexample, one study[50] found that the use of DHA-rich fish oil capsules did not reduce postpartum depression inmothers or improve cognitive and language development in their offspring during early childhood (though this is nota negative effect, only shows no effect).Additional studies confirmed DHA benefits for other nervous system functions, cardiovascular health, andpotentially other organs. In one study, men who took DHA supplements for 6–12 weeks decreased theconcentrations of several inflammatory markers in their blood by approximately 20%.[51] It has been shown thatheart disease patients with higher intakes of DHA and EPA survived longer. A new study found that higher intake ofDHA was associated with slower rates of telomere shortening, which is a basic DNA-level marker of aging.[52]

Preliminary studies showed that a high intake of DHA was associated with reduced risk for developing Alzheimer'sdisease and Parkinson's Disease [53] consistent with DHA being the most abundant omega-3 fatty acid in the brain. Itis now considered so important to brain and eye development that DHA is included in most infant formulas.[54]

Lastly, in preliminary research, it was found that a diet rich in DHA might protect stroke victims from brain damageand disability and aid in a speedier recovery.[55]

According to a new study, DHA is very likely important in the formation of the acrosome, an arc-like structure onthe top of sperm, which is critical in fertilization because it houses a variety of enzymes that sperm use to penetratean egg[56]. Because humans and other mammals are able to make their own DHA from other fatty acids, DHAdeficiency isn't very common. But, if that DHA-synthesizing enzyme is defective, it could lead to problems withinfertility[57]

NutritionOrdinary types of cooked salmon contain 500–1500 mg DHA and 300–1000 mg EPA per 100 grams.(USDA) [58]

Additional top fish sources of DHA are: tuna, bluefish, mackerel, swordfish, anchovies, herring, sardines, and caviar.

The discovery of algae-based DHAIn the early 1980s, NASA-sponsored scientific research in search of a plant-based food source that could generateoxygen and nutrition on long-duration space flights. The researchers discovered that certain species of marine algaeproduced rich nutrients. This research led to the development of an algae-based, vegetable-like oil that contains twoessential polyunsaturated fatty acids: DHA and ARA (Arachidonic acid).[59]

Docosahexaenoic acid 144

Use as a food additiveDHA is widely used as a food supplement. It was first used primarily in infant formulas.[60] In 2004, the US Foodand Drug Administration endorsed qualified health claims for DHA,[61] and by 2007 DHA-fortified dairy items(milk, yogurt, cooking oil) started to appear in grocery stores.DHA is believed to be helpful to people with a history of heart disease, for premature infants, and to support healthybrain development especially in young children along with supporting retinal development. Some manufacturedDHA is a vegetarian product extracted from algae, and it competes on the market with fish oil that contains DHAand other omega-3's such as EPA. Both fish oil and DHA are odorless and tasteless after processing as a foodadditive .[62]

Studies of vegetarians and vegansVegetarian diets typically contain limited amounts of DHA, and vegan diets typically contain no DHA. Vegetariansand vegans have substantially lower levels of DHA in their bodies, and short-term supplemental ALA has beenshown to increase EPA, but not DHA. However, supplemental preformed DHA, available in algae-derived oils orcapsules, has been shown to increase DHA levels. While there is little evidence of adverse health or cognitive effectsdue to DHA deficiency in adult vegetarians or vegans, fetal and breast milk levels remain a concern.[63]

DHA and EPA in fish oilsFish oil is widely sold in gelatin capsules containing a mixture of omega-3 fatty acids including EPA and smallerquantities of DHA. One study found fish oil higher in DHA than EPA lowered inflammatory cytokines, such as IL-6and IL-1β, associated with neurodegenerative and autoimmune diseases. They note the brain normally containsDHA, but not EPA, though both DHA and EPA plasma concentrations increased significantly for participants.[64]

Hypothesized role in human evolutionAn abundance of DHA in seafood has been suggested as being helpful in the development of a large brain,[65]

though other researchers claim a terrestrial diet could also have provided the necessary DHA.[66]

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[43] DHASCO and ARASCO in Infant Formula - Food Standards (http:/ / www. foodstandards. gov. au/ _srcfiles/ DHASCO and ARASCO ininfant formula. pdf)

[44] Harnam, F; F. Shahidi (May 2004). "Synthesis of structured lipids via acidolysis of docosahexaenoic acid single-cell oil (DHASCO) withcapric acid" (http:/ / www. ncbi. nlm. nih. gov/ pubmed/ 15137833). J Agric Food Chem 52 (10): 2900–2906. doi:10.1021/jf035316f.PMID 15137833. .

[45] Malone, J. P. (2011, April). The systems theory of autistogenesis and its evolutionary implications. Poster presented at the WesternPsychological Association 91st Annual Convention, Los Angeles, CA. Convention program retrieved from http:/ / www. westernpsych. org/pdf/ WPA%202011%203rd%20Proof. pdf.

[46] Connell, Gary, J. et al. (2001-07-26). "SOLVENTLESS EXTRACTION PROCESS" (http:/ / www. wipo. int/ ipdl/ IPDL-CIMAGES/ view/pct/ getbykey5?KEY=01/ 53512. 010726& ELEMENT_SET=DECL). . Retrieved February 8, 2006. A patent at the WIPO.

[47] Replacing Mother—Imitating Human Breast Milk in the Laboratory. The Cornucopia Institute. January 2008 (http:/ / www. cornucopia. org/2008/ 01/ replacing-mother-infant-formula-report/ )

[48] Clandinin M, Van Aerde J, Merkel K, Harris C, Springer M, Hansen J, Diersen-Schade D (2005). "Growth and development of preterminfants fed infant formulas containing docosahexaenoic acid and arachidonic acid". J Pediatr 146 (4): 461–8. doi:10.1016/j.jpeds.2004.11.030.PMID 15812447.

[49] Ramakrishnan, Usha; et al. (8/01/11). "Prenatal Docosahexaenoic Acid Supplementation and Infant Morbidity: Randomized ControlledTrial" (http:/ / pediatrics. aappublications. org/ content/ early/ 2011/ 07/ 28/ peds. 2010-1386). Journal of the American Academy of Pediatrics.doi:10.1542/peds.2010-1386. .

[50] Maria Makrides, "The Effects of DHA Supplementation During Pregnancy on Maternal Depression and Neurodevelopment of YoungChildren." The Journal of American Medical Association http:/ / jama. ama-assn. org/ content/ 304/ 15/ 1675. abstract

[51][51] Kelley DS et al. DHA supplementation decreases serum C-reactive protein and other markers of inflammation in hypertriglyceridemic men.J Nutr. 2009 Mar;139(3):495-501. Epub 2009 Jan 21.

[52][52] Farzaneh-Far R et al. Association of Marine Omega-3 Fatty Acid Levels With Telomeric Aging in Patients With Coronary HeartDiseaseJAMA. 2010;303(3):250-257.

[53] http:/ / www. ncbi. nlm. nih. gov/ pmc/ articles/ PMC3221408/[54] Aline Hittle. "DHA in Slowing the Progression of AD." Baylor College of Medicine. http:/ / www. bcm. edu/ neurology/ alzheimers/ index.

cfm?pmid=16413[55][55] "Kathleen Blanchard. "DHA in Fish Oil Could Protect from Stroke Disability." Louisiana State University.[56][56] University of Illinois College of Agricultural, Consumer and Environmental Sciences (2012, January 18). Dietary DHA linked to male

fertility[57] http:/ / www. livescience. com/ 17878-dha-vital-sperm-health. html[58] http:/ / www. health. gov/ dietaryguidelines/ dga2005/ report/ html/ table_g2_adda2. htm[59] Jones, John. "Nutritional Products from Space Research" (http:/ / www. sti. nasa. gov/ tto/ spinoff1996/ 42. html). May 1st, 2001. NASA. .[60] "FDA: Why is there interest in adding DHA and ARA to infant formulas?" (http:/ / www. fda. gov/ Food/ FoodSafety/

Product-SpecificInformation/ InfantFormula/ ConsumerInformationAboutInfantFormula/ ucm108558. htm). US Food & Drug Administration.. Retrieved July, 2002.

[61] "FDA Announces Qualified Health Claims for Omega-3 Fatty Acids". US Food & Drug Administration.[62] Rivlin, Gary (2007-01-14). "Magical or Overrated? A Food Additive in a Swirl" (http:/ / www. nytimes. com/ 2007/ 01/ 14/ business/

yourmoney/ 14omega. html?_r=1). The New York Times. . Retrieved 2007-01-15.[63] Sanders, Thomas A.B. (August–September 2009). "DHA status of vegetarians". Prostaglandins, Leukotrienes, and Essential Fatty Acids

(International Society for the Study of Fatty Acids and Lipids) 81 (2–3): 137–141. doi:10.1016/j.plefa.2009.05.013. ISSN 0952-3278.PMID 19500961.

[64] Vedin I et al. (1 June 2008). "Effects of docosahexaenoic acid–rich n–3 fatty acid supplementation on cytokine release" (http:/ / www. ajcn.org/ cgi/ content/ abstract/ 87/ 6/ 1616). Am J Clin Nutr 87 (6): 1616–1622. PMID 18541548. .

[65] Crawford, M et al. (2000). "Evidence for the unique function of docosahexanoic acid (DHA) during the evolution of the modern hominidbrain". Lipids 34 (S1): S39–S47. doi:10.1007/BF02562227. PMID 10419087.

Docosahexaenoic acid 147

[66] Carlson BA, Kingston JD (2007). "Docosahexaenoic acid biosynthesis and dietary contingency: Encephalization without aquatic constraint".Am. J. Hum. Biol. 19 (4): 585–8. doi:10.1002/ajhb.20683. PMID 17546613.

External links• DHA / EPA Omega-3 Institute (http:/ / www. dhaomega3. org) – Recent studies, overviews, and objective

science.• Docosahexaenoic acid (DHA) (http:/ / www. umm. edu/ altmed/ articles/ docosahexaenoic-acid-000300. htm) –

University of Maryland Medical Center (UMMC)• Docosahexaenoic acid - DHA (http:/ / chemsub. online. fr/ name/ docosahexaenoic_acid. html) ChemSub Online

Caprylic acid 148

Caprylic acid

Caprylic acid

Identifiers

CAS number 124-07-2 [1] 

PubChem 379 [2]

ChemSpider 370 [3] 

UNII OBL58JN025 [4] 

DrugBank DB04519 [5]

KEGG D05220 [6] 

ChEBI CHEBI:28837 [7] 

ChEMBL CHEMBL324846 [8] 

Jmol-3D images Image 1 [9]

Properties

Molecular formula C8H16O2

Molar mass 144.21 g/mol

Appearance Oily colorless liquid

Density 0.910 g/cm3[10]

Melting point 16.7 °C, 290 K, 62 °F ([11])

Boiling point 239.7 °C, 513 K, 463 °F ([10])

Solubility in water 0.068 g/100 mL[10]

Acidity (pKa) 4.89[12]

Hazards

LD50 10.08 g/kg (orally in rats)[10]

  (verify) [13] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm

Caprylic acid 149

kernel oil.[11] It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell andtaste.[10]

Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15% ingoat milk fat.

UsesCaprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture ofdyes.Caprylic acid is also used in the treatment of some bacterial infections. Due to its relatively short chain length it hasno difficulty in penetrating fatty cell wall membranes, hence its effectiveness in combating certain lipid-coatedbacteria, such as Staphylococcus aureus and various species of Streptococcus.[14]

Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handlingestablishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants.It is also used as disinfectant in health care facilities, schools/colleges, animal care/veterinary facilities, industrialfacilities, office buildings, recreational facilities, retail and wholesale establishments, livestock premises, restaurants,and hotels/motels. In addition, caprylic acid is used as an algaecide, bactericide, and fungicide in nurseries,greenhouses, garden centers, and interiorscapes on ornamentals. Products containing caprylic acid are formulated assoluble concentrate/liquids and ready-to-use liquids.[15]

Caprylic acid must be covalently linked to the serine residue at the 3-position of ghrelin, specifically, it must acylatethe -OH group, for ghrelin to have its hunger-stimulating action on the feeding centers of the hypothalamus, thoughother fatty acids may have similar effects.The octanoic acid breath test is used to measure gastric emptying. Some potential benefit is possible fromadministration of octanoic acid for patients with essential tremor.The acid chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=124-07-2[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=379[3] http:/ / www. chemspider. com/ 370[4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=OBL58JN025[5] http:/ / www. drugbank. ca/ drugs/ DB04519[6] http:/ / www. kegg. jp/ entry/ D05220[7] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28837[8] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL324846[9] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCC%28%3DO%29O[10] Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123[11] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/

publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. .[12] Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.[13] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443496721& page2=%3ACaprylic+ acid[14] Nair MK, Joy J, Vasudevan P, Hinckley L, Hoagland TA, Venkitanarayanan KS (Oct 2005). "Antibacterial effect of caprylic acid and

monocaprylin on major bacterial mastitis pathogens". J Dairy Sci 88 (10): 3488–95. doi:10.3168/jds.S0022-0302(05)73033-2.PMID 16162522.

[15][15] EPA - Antimicrobials Division - www.regulations.gov - Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.

Decanoic acid 150

Decanoic acid

Decanoic acid

Identifiers

CAS number 334-48-5 [1]  , 1002-62-6 [2] (sodium salt)

PubChem 2969 [3]

ChemSpider 2863 [4] 

UNII 4G9EDB6V73 [5] 

DrugBank DB03838 [6]

KEGG C01571 [7] 

ChEBI CHEBI:30813 [8] 

ChEMBL CHEMBL107498 [9] 

Jmol-3D images Image 1 [10]

Properties

Molecular formula C10H20O2

Molar mass 172.26 g mol−1

Appearance White crystals with strong smell

Density 0.893 g/cm3

Melting point 31.6 °C, 305 K, 89 °F ([11])

Boiling point 269 °C, 542 K, 516 °F

Solubility in water immiscible

Hazards

MSDS External MSDS [12]

R-phrases R36 R38

S-phrases S24 S25 S26 S36 S37 S39

Main hazards Medium toxicityMay cause respiratory irritationMay be toxic on ingestionMay be toxic on skin contact

Related compounds

Decanoic acid 151

Related fatty acids Caprylic acidLauric acid

Related compounds DecanolDecanal

  (verify) [13] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Decanoic acid, or capric acid, is a saturated fatty acid. Its formula is CH3(CH2)8COOH. Salts and esters ofdecanoic acid are called decanoates or "caprates". The term capric acid arises from the Latin "capric" which pertainsto goats due to their olfactory similarities.[14]

Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otheriwse it is uncommon intypical seed oils.[15] It is found in the milk of various mammals and to a lesser extent in other animal fats.[11]

Two other acids are named after goats: caproic (a C6 fatty acid) and caprylic (a C8 fatty acid). Along with decanoicacid, these total 15% in goat milk fat.

ProductionDecanoic acid can be prepared from oxidation of primary alcohol decanol, by using chromium trioxide (CrO3)oxidant under acidic conditions.[16]

Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide willgive sodium decanoate. This salt (CH3(CH2)8COO-Na+) is a component of some types of soap.

UseManufacturing of esters for artificial fruit flavors and perfumes. Also as an intermediate in chemical syntheses. It isused in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics,food additives and pharmaceuticals.[17]

PharmaceuticalsDecanoate salts and esters of various drugs are available. Since decanoic acid is a fatty acid, forming a salt or esterwith a drug will increase its lipophilicity and its affinity for fatty tissue. Since distribution of a drug from fatty tissueis usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using itsdecanoate form. Some examples of drugs available as a decanoate ester or salt include nandrolone, fluphenazine,bromperidol, haloperidol and vanoxerine.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=334-48-5[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=1002-62-6[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=2969[4] http:/ / www. chemspider. com/ 2863[5] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=4G9EDB6V73[6] http:/ / www. drugbank. ca/ drugs/ DB03838[7] http:/ / www. kegg. jp/ entry/ C01571[8] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=30813[9] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL107498[10] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCC[11] "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/ publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73

(4): 685–744. 2001. doi:10.1351/pac200173040685. .

Decanoic acid 152

[12] http:/ / physchem. ox. ac. uk/ MSDS/ DE/ decanoic_acid. html[13] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=450974113& page2=%3ADecanoic+ acid[14] "capri-, capr- +" (http:/ / wordinfo. info/ unit/ 371). . Retrieved 9/28/2012.[15] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[16] John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624[17] Capric Acid (http:/ / www. chemicalland21. com/ industrialchem/ organic/ CAPRIC ACID. htm)

Lauric acid 153

Lauric acid

Lauric acid

Identifiers

CAS number 143-07-7 [1] 

PubChem 3893 [2]

ChemSpider 3756 [3] 

ChEMBL CHEMBL108766 [4] 

Jmol-3D images Image 1 [5]

Properties

Molecular formula C12H24O2

Molar mass 200.31776

Appearance white powder

Odor slight odor of bay oil

Density 0.880 g/cm3

Melting point 43.2 °C[6]

Boiling point 298.9 °C

Solubility in water 0.006 g/100 mL (20 °C)

Refractive index (nD) 1.423

Viscosity 7.30 mPa·s at 323 K

Hazards

NFPA 704

Flash point ≥ 110 °C

Related compounds

Related compounds Glyceryl laurate

  (verify) [7] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Lauric acid (systematically: dodecanoic acid), the saturated fatty acid with a 12-carbon atom chain, thus falling intothe medium chain fatty acids, is a white, powdery solid with a faint odor of bay oil or soap.

Lauric acid 154

OccurrenceLauric acid, as a component of triglycerides, comprises about half of the fatty acid content in coconut oil, laurel oil,and in palm kernel oil (not to be confused with palm oil),[8][9] Otherwise it is relatively uncommon. It is also foundin human breast milk (6.2% of total fat), cow's milk (2.9%), and goat's milk (3.1%).[8]

PropertiesLike many other fatty acids, lauric acid is inexpensive, has a long shelf-life, and is non-toxic and safe to handle. It ismainly used for the production of soaps and cosmetics. For these purposes, lauric acid is neutralized with sodiumhydroxide to give sodium laurate, which is a soap. Most commonly, sodium laurate is obtained by saponification ofvarious oils, such as coconut oil. These precursors give mixtures of sodium laurate and other soaps.[9]

Niche usesIn the laboratory, lauric acid is often used to investigate the molar mass of an unknown substance via thefreezing-point depression. Lauric acid is convenient because its melting point when pure is relatively high (43.2 °C).Its cryoscopic constant is 3.9 K·kg/mol. By melting lauric acid with the unknown substance, allowing it to cool, andrecording the temperature at which the mixture freezes, the molar mass of the unknown compound may bedetermined.[10]

Potential medicinal propertiesLauric acid has been claimed to have antimicrobial properties.[11][12][13][14]

Lauric acid has been found to increase total cholesterol the most of all fatty acids. But most of the increase isattributable to an increase in high-density lipoprotein (HDL) "good" cholesterol. As a result, lauric acid has "a morefavorable effect on total:HDL cholesterol than any other fatty acid, either saturated or unsaturated";[15] a lowertotal/HDL cholesterol ratio suggests a decrease in atherosclerotic risk.[16]

Lauric acid converts to the monoglyceride monolaurin in the body.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=143-07-7[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=3893[3] http:/ / www. chemspider. com/ 3756[4] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL108766[5] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCC[6] Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.[7] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=417697408& page2=%3ALauric+ acid[8] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/

publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. .[9][9] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[10] "Using Freezing Point Depression to find Molecular Weight" (https:/ / eee. uci. edu/ programs/ gchem/ 02MANfrzptdep. pdf). University of

California, Irvine. 2010-04-12. .[11] Hoffman KL, Han IY, Dawson PL (2001). "Antimicrobial effects of corn zein films impregnated with nisin, lauric acid, and EDTA". J.

Food Prot. 64 (6): 885–9. PMID 11403145.[12] Ouattar B, Simard RE, Piett G, Bégin A, Holley RA (2000). "Inhibition of surface spoilage bacteria in processed meats by application of

antimicrobial films prepared with chitosan". Int. J. Food Microbiol. 62 (1–2): 139–48. doi:10.1016/S0168-1605(00)00407-4.PMID 11139014.

[13] PL Dawson, GD Carl, JC Acton, and IY Han (1 May 2002). "Effect of lauric acid and nisin-impregnated soy-based films on the growth ofListeria monocytogenes on turkey bologna" (http:/ / ps. fass. org/ cgi/ content/ abstract/ 81/ 5/ 721) (Free full text). Poultry Science 81 (5):721–726. PMID 12033424. .

Lauric acid 155

[14] Alexey Ruzin and Richard P. Novick (May 2000). "Equivalence of Lauric Acid and Glycerol Monolaurate as Inhibitors of SignalTransduction in Staphylococcus aureus" (Free full text). J Bacteriol 182 (9): 2668–2671. doi:10.1128/JB.182.9.2668-2671.2000.PMC 111339. PMID 10762277.

[15] Mensink RP, Zock PL, Kester ADM, Katan MB (May 2003). "Effects of dietary fatty acids and carbohydrates on the ratio of serum total toHDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials" (http:/ / www. ajcn. org/ content/ 77/ 5/1146. full?ijkey=846a72387ebc0d82545acd5442a0c3a9e9fc3566). American Journal of Clinical Nutrition 77 (5): 1146–1155.ISSN 0002-9165. PMID 12716665. .

[16] Thijssen, M.A. and R.P. Mensink. (2005). Fatty Acids and Atherosclerotic Risk (http:/ / books. google. com/ books?id=kvo6BN1AGNAC&pg=PA171& dq=#v=onepage& q& f=false). In Arnold von Eckardstein (Ed.) Atherosclerosis: Diet and Drugs. Springer. pp. 171–172. ISBN978-3-540-22569-0.

Appendix: occurrence of lauric acid in various foods• The palm tree Orbignya phalerata Mart, a species popularly known in Brazil as babassu. 50% in babassu oil.• Attalea cohune, the cohune palm (also rain tree, American oil palm, corozo palm or manaca palm) 46.5% in

cohune oil.• Astrocaryum murumuru (Arecaceae) a palm native to the Amazon, 47.5% in "murumuru butter".• Coconut and Coconut oil• Pycnanthus kombo (African nutmeg)• Virola surinamensis (wild nutmeg) 7.8–11.5%• Peach palm seed 10.4%• Betel nut 9%• Date palm seed 0.56–5.4%• Macadamia nut 0.072–1.1%• Plum 0.35–0.38%• Watermelon seed 0.33%• Citrullus lanatus (egusi melon)• Pumpkin flower 205 ppm, pumpkin seed 472 ppm

Further reading• Berner, Louise A. (1993). Defining the Role of Milkfat in Balanced Diets. In John E. Kinsella (Ed.) Advances in

Food and Nutrition Research – Volume 37. Academic Press. pp. 159–166 (http:/ / books. google. com/books?id=wflcBD1PKx8C& pg=PA159& dq=#v=onepage& q& f=false). ISBN 978-0-12-016437-0.

• Kabara, Jon J. (1978). The Pharmacological Effect of Lipids (http:/ / books. google. com/books?id=zQSzj1hcYVkC& printsec=frontcover& dq=#v=onepage& q& f=false). Champaign IL: American OilChemist's Society. ISBN 9991817697.

• Kabara, Jon J. (2008). Fats Are Good for You and Other Secrets – How Saturated Fat and Cholesterol ActuallyBenefit the Body (http:/ / books. google. com/ books?id=z8EoP-5sZ6sC& printsec=frontcover&source=gbs_ge_summary_r& cad=0#v=onepage& q& f=false). North Atlantic Books. ISBN 1-55643-690-4.

Myristic acid 156

Myristic acid

Myristic acid[1]

Identifiers

CAS number 544-63-8 [2] 

PubChem 11005 [3]

ChemSpider 10539 [4] 

ChEMBL CHEMBL111077 [5] 

Jmol-3D images Image 1 [6]

Properties

Molecular formula C14H28O2

Molar mass 228.37092

Density 0.8622 g/cm3

Melting point 54.4 °C[7]

Boiling point 250.5 °C at 100 mmHg

  (verify) [8] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Myristic acid, also called tetradecanoic acid, is a common saturated fatty acid with the molecular formulaCH3(CH2)12COOH. A myristate is a salt or ester of myristic acid.Myristic acid is named after the nutmeg Myristica fragrans. Nutmeg butter is 75% trimyristin, the triglyceride ofmyristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minorcomponent of many other animal fats.[7] It is also found in spermaceti, the crystallized fraction of oil from the spermwhale.Myristic acid is also commonly added co-translationally to the penultimate, nitrogen-terminus, glycine inreceptor-associated kinases to confer the membrane localisation of the enzyme. The myristic acid has a sufficientlyhigh hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasmamembrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes.The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption throughthe skin is desired.Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

Myristic acid 157

References[1] Merck Index, 11th Edition, 6246[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=544-63-8[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=11005[4] http:/ / www. chemspider. com/ 10539[5] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL111077[6] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCCCCCCCC%28%3DO%29O[7] "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/ publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73

(4): 685–744. 2001. doi:10.1351/pac200173040685. .[8] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=396344370& page2=%3AMyristic+ acid

Palmitic acid 158

Palmitic acid

Palmitic acid[1]

Identifiers

CAS number 57-10-3 [2] 

PubChem 985 [3]

ChEMBL CHEMBL82293 [4] 

IUPHAR ligand 1055 [5]

Jmol-3D images Image 1 [6]

Properties

Molecular formula C16H32O2

Molar mass 256.42 g/mol

Appearance White crystals

Density 0.853 g/cm3 at 62 °C

Melting point 62.9 °C[7]

Boiling point 351-352 °C[8]

215 °C at 15 mmHg

Solubility in water Insoluble

Acidity (pKa) 4.78

Hazards

NFPA 704

  (verify) [9] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common fatty acid found in animals,plants and microorganisms.[10] Its molecular formula is CH3(CH2)14CO2H. As its name indicates, it is a majorcomponent of the oil from palm trees (palm oil, palm kernel oil, and coconut oil), but can also be found in meats,cheeses, butter, and dairy products. Palmitate is a term for the salts and esters of palmitic acid. The palmitate anion isthe observed form of palmitic acid at basic pH.

Palmitic acid 159

Palmitic acid has been shown (in rats fed on a 20% fat (palmitic acid), 80% carbohydrate diet) to alter aspects of thecentral nervous system responsible for the secretion of insulin, and to suppress the body's naturalappetite-suppressing signals from leptin and insulin—the key hormones involved in weight regulation.[11]

Aluminum salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm(aluminum naphthenate and aluminum palmitate). The word "napalm" is derived from the words naphthenic acidand palmitic acid.

Occurrence and productionPalmitic acid mainly occurs as its ester in triglycerides (fats), especially palm oil but also tallow. The cetyl ester ofpalmitic acid (cetyl palmitate) occurs in spermaceti. It was discovered by Edmond Frémy in 1840, in saponified palmoil.[12] Butter, cheese, milk and meat also contain this fatty acid.Palmitic acid is prepared by treating fats and oils with water at a high pressure and temperature (above 200 °C),leading to the hydrolysis of triglycerides. The resulting mixture is then distilled.[13]

BiochemistryExcess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced duringfatty acid synthesis and the precursor to longer fatty acids. Palmitate negatively feeds back on acetyl-CoAcarboxylase (ACC), which is responsible for converting acetyl-CoA to malonyl-CoA, which in turn is used to add tothe growing acyl chain, thus preventing further palmitate generation.[14] In biology, some proteins are modified bythe addition of a palmitoyl group in a process known as palmitoylation. Palmitoylation is important for membranelocalisation of many proteins.

ApplicationsPalmitic acid is mainly used to produce soaps, cosmetics, and release agents. These applications utilize sodiumpalmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from thecoconut palm nut, is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis ofthe ester groups. This procedure affords glycerol and sodium palmitate.Because it is inexpensive and adds texture to processed foods (convenience food), palmitic acid and its sodium saltfind wide use including foodstuffs. Sodium palmitate is permitted as a natural additive in organic products.[15]

Hydrogenation of palmitic acid yields cetyl alcohol, which is used to produce detergents and cosmetics.Recently, a long-acting antipsychotic medication, paliperidone palmitate (marketed as INVEGA Sustenna), used inthe treatment of schizophrenia, has been synthesized using the oily palmitate ester as a long-acting release carriermedium when injected intramuscularly. The underlying method of drug delivery is similar to that used with decanoicacid to deliver long-acting depot medication, in particular, neuroleptics such as haloperidol decanoate.

Palmitic acid 160

Dietary effectAccording to the World Health Organization, evidence is "convincing" that consumption of palmitic acid increasesrisk of developing cardiovascular diseases, placing it in the same evidence category as trans fatty acids.[16] Retinylpalmitate is an antioxidant and a source of vitamin A added to low fat milk to replace the vitamin content lostthrough the removal of milk fat. Palmitate is attached to the alcohol form of vitamin A, retinol, to make vitamin Astable in milk.

References[1] Merck Index, 12th Edition, 7128.[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=57-10-3[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=985[4] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL82293[5] http:/ / www. iuphar-db. org/ DATABASE/ LigandDisplayForward?ligandId=1055[6] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCCCCCCCCCC%28%3DO%29O[7] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/

publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. .[8] Palmitic acid (http:/ / www. inchem. org/ documents/ icsc/ icsc/ eics0530. htm) at Inchem.org[9] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=415315408& page2=%3APalmitic+ acid[10][10] Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN

0849396883 | ISBN 978-0849396885[11] Palmitic acid mediates hypothalamic insulin resistance by altering PKC-θ subcellular localization in rodents (http:/ / www. jci. org/ articles/

view/ 36714), Journal of Clinical Investigation[12] E. Frémy, Memoire sur les produits de la saponification de l’huile de palme, Journal de Pharmacie et de Chimie XII (1842), p. 757.[13][13] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[14] Fatty acid biosynthesis - Reference pathway (http:/ / www. genome. jp/ kegg/ pathway/ map/ map00061. html)[15][15] US Soil Association standard 50.5.3[16] Diet, Nutrition and the Prevention of Chronic Diseases (http:/ / www. freezepage. com/ 1348239076FHWAJDADVT), WHO Technical

Report Series 916, Report of a Joint WHO/FAO Expert Consultation, World Health Organization, Geneva, 2003, p. 88 (Table 10)

Stearic acid 161

Stearic acid

Stearic acid[1]

Identifiers

CAS number 57-11-4 [2] 

PubChem 5281 [3]

DrugBank DB03193 [4]

ChEMBL CHEMBL46403 [5] 

Jmol-3D images Image 1 [6]

Properties

Molecular formula C18H36O2

Molar mass 284.48 g mol−1

Appearance white solid

Density 0.847 g/cm3 at 70 °C

Melting point 69.6 °C, 343 K, 157 °F

Boiling point 383 °C, 656 K, 721 °F

Solubility in water 3 mg/L (20 °C)

Refractive index (nD) 1.4299

Hazards

NFPA 704

  (verify) [7] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Stearic acid (STAIR-ik or STEER-ik) is the saturated fatty acid with an 18 carbon chain and has the IUPAC nameoctadecanoic acid. It is a waxy solid, and its chemical formula is CH3(CH2)16CO2H. Its name comes from theGreek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. Stearic acidis one of the most common saturated fatty acids found in nature following palmitic acid.[8]

Stearic acid 162

ProductionIt occurs in many animal and vegetable fats and oils, but it is more abundant in animal fat (up to 30%) than vegetablefat (typically <5%). The important exceptions are cocoa butter and shea butter where the stearic acid content (as atriglyceride) is 28–45%.[9]

Stearic acid is prepared by treating these fats and oils with water at a high pressure and temperature (above 200 °C),leading to the hydrolysis of triglycerides. The resulting mixture is then distilled.[10] Commercial stearic acid is oftena mixture of stearic and palmitic acids, although purified stearic acid is available.In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery viaacetyl-CoA.

UsesGenerally applications of stearic acid exploit its bifunctional character, with a polar head group that can be attachedto metal cations and a nonpolar chain that confers solubility in organic solvents. The combination leads to uses as asurfactant and softening agent. Stearic acid undergoes the typical reactions of saturated carboxylic acids, notablyreduction to stearyl alcohol, and esterification with a range of alcohols.

Soaps, cosmetics, detergentsStearic acid is mainly used in the production of detergents, soaps, and cosmetics such as shampoos and shavingcream products. Soaps are not made directly from stearic acid, but indirectly by saponification of triglyceridesconsisting of stearic acid esters. Esters of stearic acid with ethylene glycol; glycol stearate and glycol distearate, areused to produce a pearly effect in shampoos, soaps, and other cosmetic products. They are added to the product inmolten form and allowed to crystallize under controlled conditions. Detergents are obtained from amides andquaternary alkylammonium derivatives of stearic acid.

Lubricants, softening and release agentsIn view of the soft texture of the sodium salt, which is the main component of soap, other salts are also useful fortheir lubricating properties. Lithium stearate is an important component of grease. The stearate salts of zinc, calcium,cadmium, and lead are used to soften PVC. Stearic acid is used along with castor oil for preparing softeners in textilesizing. They are heated and mixed with caustic potash or caustic soda. Related salts are also commonly used asrelease agents, e.g. in the production of automobile tires.

Niche usesBeing inexpensively available and chemically benign, stearic acid finds many niche applications. When makingplaster castings from a plaster piece mold or waste mold and when making the mold from a shellacked clay original.In this use, powdered stearic acid is dissolved in water and the solution is brushed onto the surface to be parted aftercasting. This reacts with the calcium in the plaster to form a thin layer of calcium stearate which functions as arelease agent. When reacted with zinc it forms zinc stearate which is used a lubricant for playing cards (fanningpowder) to ensure a smooth motion when fanning. In compressed confections it is used as a lubricant to keep thetablet from sticking to the die.Fatty acids are classic components of candle-making. Stearic acid is used along with simple sugar or corn syrup as ahardener in candies.Stearic acid is used to produce dietary supplements.In fireworks, stearic acid is often used to coat metal powders such as aluminium and iron. This prevents oxidation,allowing compositions to be stored for a longer period of time.

Stearic acid 163

Stearic acid is a common lubricant during injection molding and pressing of ceramic powders.[11] It is also used as amold release for foam latex that is baked in stone molds.

MetabolismAn isotope labeling study in humans[12] concluded that the fraction of dietary stearic acid oxidatively desaturated tooleic acid was 2.4 times higher than the fraction of palmitic acid analogously converted to palmitoleic acid. Also,stearic acid was less likely to be incorporated into cholesterol esters. In epidemiologic and clinical studies stearicacid was associated with lowered LDL cholesterol in comparison with other saturated fatty acids.[13] These findingsmay indicate that stearic acid is healthier than other saturated fatty acids.

References[1] Susan Budavari, ed. (1989). Merck Index (11th ed.). Rahway, New Jersey: Merck & Co., Inc. p. 8761. ISBN 978-0-911910-28-5.[2] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=57-11-4[3] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=5281[4] http:/ / www. drugbank. ca/ drugs/ DB03193[5] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL46403[6] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCCCCCCCCCCCC%28%3DO%29O[7] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=458266068& page2=%3AStearic+ acid[8][8] Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. ISBN

0849396883 | ISBN 978-0849396885[9] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/

publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. .[10][10] David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia

of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2[11] Tsenga, Wenjea J.; Mo Liua, Dean; Hsub, Chung-King (1999). "Influence of stearic acid on suspension structure and green microstructure

of injection-molded zirconia ceramics". Ceramics International 25 (2): 191–195. doi:10.1016/S0272-8842(98)00024-8.[12] Emken, Edward A. (1994). "Metabolism of dietary stearic acid relative to other fatty acids in human subjects". American Journal of Clinical

Nutrition 60 (6): 1023S–1028S. PMID 7977144.[13] Hunter, J. Edward; Zhang, Jun; Kris-Etherton, Penny M. (January 2010). "Cardiovascular disease risk of dietary stearic acid compared with

trans, other saturated, and unsaturated fatty acids: a systematic review". Am. J. Clinical Nutrition (American Society for Nutrition) 91 (1):46–63. doi:10.3945/ajcn.2009.27661. ISSN 0002-9165. PMID 19939984.

External links• NIST Chemistry WebBook Entry (http:/ / webbook. nist. gov/ cgi/ cbook. cgi?Name=stearic+ acid& Units=SI)

Arachidic acid 164

Arachidic acid

Arachidic acid

Identifiers

CAS number 506-30-9 [1] 

PubChem 10467 [2]

ChemSpider 10035 [3] 

KEGG C06425 [4] 

ChEBI CHEBI:28822 [5] 

ChEMBL CHEMBL1173381 [6] 

Jmol-3D images Image 1 [7]

Properties[8]

Molecular formula C20H40O2

Molar mass 312.53 g mol−1

Appearance White crystalline solid

Density 0.8240 g/cm3

Melting point 75.5 °C, 349 K, 168 °F

Boiling point 328 °C, 601 K, 622 °F

Solubility in water Practically insoluble in water

Hazards

Flash point 169.7 °C

  (verify) [9] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Arachidic acid, also called eicosanoic acid, is the saturated fatty acid with a 20 carbon chain. It is as a minor constituent of peanut oil (1.1%–1.7%)[10] and corn oil (3%).[11] Its name derives from the Latin arachis — peanut. It

Arachidic acid 165

can be formed by the hydrogenation of arachidonic acid.Reduction of arachidic acid yields arachidyl alcohol.Arachidic acid is used for the production of detergents, photographic materials and lubricants.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=506-30-9[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=10467[3] http:/ / www. chemspider. com/ 10035[4] http:/ / www. kegg. jp/ entry/ C06425[5] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28822[6] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL1173381[7] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCCCCCCCCCC[8] *Merck Index, 11th Edition, 791[9] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443396639& page2=%3AArachidic+ acid[10] Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/

publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685. .[11] U.S. Department of Agriculture, Agricultural Research Service. 2007. USDA National Nutrient Database for Standard Reference, Release

20. Nutrient Data Laboratory Home Page (http:/ / www. ars. usda. gov/ ba/ bhnrc/ ndl)

Behenic acid 166

Behenic acid

Behenic acid

Identifiers

CAS number 112-85-6 [1] 

PubChem 8215 [2]

ChemSpider 7923 [3] 

UNII H390488X0A [4] 

EC number 204-010-8 [5]

KEGG C08281 [6] 

ChEBI CHEBI:28941 [7] 

ChEMBL CHEMBL1173474 [8] 

Jmol-3D images Image 1 [9]

Properties

Molecular formula C22H44O2

Molar mass 340.58 g mol−1

Appearance White to yellowish crystals or powder

Melting point 80.0 °C[10]

Boiling point 306 °C

Hazards

NFPA 704

  (verify) [11] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Behenic acid 167

Behenic acid comes from the ben oil tree, Moringa oleifera

Behenic acid (also docosanoic acid) is a normalcarboxylic acid, the saturated fatty acid with formulaC21H43COOH. In appearance, it consists of white tocream color crystals or powder with a melting point of80 °C and boiling point of 306 °C.

Sources

At 9%, it is a major component of Ben oil (or behen oil),which is extracted from the seeds of the Ben-oil tree(Moringa oleifera). It is so named from the Persian monthBahman, when the roots of this tree were harvested.[12]

Behenic acid is also present in some other oils andoil-bearing plants, including rapeseed (canola) and peanutoil and skins. It is estimated that one ton of peanut skinscontains 13 pounds (5.9 kg) of behenic acid.[13]

Properties

As a dietary oil, behenic acid is poorly absorbed. In spiteof its low bioavailability compared with oleic acid,behenic acid is a cholesterol-raising saturated fatty acid inhumans.[14]

UsesCommercially, behenic acid is often used to give hair conditioners and moisturizers their smoothing properties.[13]

Also used in lubricating oils, as solvent evaporation retarder in paint removers. Amide as anti-foam in themanufacturing of detergents, in floor polishes and dripless candles. Reduction of behenic acid yields behenylalcohol.Pracaxi oil (from the seeds of Pentaclethra macroloba) is a natural product with one of the highest concentrations ofbehenic acid, and is used in hair conditioners.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=112-85-6[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=8215[3] http:/ / www. chemspider. com/ 7923[4] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=H390488X0A[5] http:/ / esis. jrc. ec. europa. eu/ lib/ einecs_IS_reponse. php?genre=ECNO& entree=204-010-8[6] http:/ / www. kegg. jp/ entry/ C08281[7] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28941[8] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL1173474[9] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCCCCCCCCCCCC[10] "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/ publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73

(4): 685–744. 2001. doi:10.1351/pac200173040685. .[11] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=443413681& page2=%3ABehenic+ acid[12] http:/ / www. numericana. com/ answer/ culture. htm[13] USDA Scientists Find Treasure in Peanut Skins (http:/ / www. hbci. com/ ~wenonah/ new/ pnutskin. htm).

Behenic acid 168

[14] Caterm, Nilo B and Margo A Denke. January 2001 Behenic acid is a cholesterol-raising saturated fatty acid in humans (http:/ / www. ajcn.org/ cgi/ content/ abstract/ 73/ 1/ 41). American Journal of Clinical Nutrition, v 73, No. 1, pp41-44..

Lignoceric acid

Lignoceric acid

Identifiers

CAS number 557-59-5 [1] 

PubChem 11197 [2]

ChemSpider 10724 [3] 

KEGG C08320 [4] 

ChEBI CHEBI:28866 [5] 

ChEMBL CHEMBL1173620 [6] 

Jmol-3D images Image 1 [7]

Properties

Molecular formula C24H48O2

Molar mass 368.63 g/mol

Melting point 84.2 °C[8]

Related compounds

Related Fatty acids Behenic acid (C22:0)Cerotic acid (C26:0)

  (verify) [9] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in woodtar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain smallamounts of lignoceric acid (1.1% – 2.2%).[8] This fatty acid is also a byproduct of lignin production.Reduction of lignoceric acid yields lignoceryl alcohol.

Lignoceric acid 169

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=557-59-5[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=11197[3] http:/ / www. chemspider. com/ 10724[4] http:/ / www. kegg. jp/ entry/ C08320[5] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=28866[6] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL1173620[7] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCCCCCCCCCCCCCC[8] "Lexicon of lipid nutrition (IUPAC Technical Report)" (http:/ / iupac. org/ publications/ pac/ 73/ 4/ 0685/ ). Pure and Applied Chemistry 73

(4): 685–744. 2001. doi:10.1351/pac200173040685. .[9] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=415680465& page2=%3ALignoceric+ acid

Cerotic acid 170

Cerotic acid

Cerotic acid

Identifiers

CAS number 506-46-7 [1] 

PubChem 10469 [2]

ChemSpider 10037 [3]

Jmol-3D images Image 1 [4]

Properties

Molecular formula C26H52O2

Molar mass 396.69 g mol−1

Appearance Crystalline solid

  (verify) [5] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Cerotic acid, or hexacosanoic acid, is a 26-carbon long-chain saturated fatty acid with the chemical formulaCH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax, and is a white crystalline solid.Cerotic acid is also a type of very long chain fatty acid that is often associated with the diseaseadrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including ceroticacid, in the peroxisome.

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=506-46-7[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=10469[3] http:/ / www. chemspider. com/ 10037[4] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28O%29CCCCCCCCCCCCCCCCCCCCCCCCC[5] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=447785712& page2=%3ACerotic+ acid

Melissic acid 171

Melissic acid

Melissic acid

Identifiers

CAS number 506-50-3 [1] 

PubChem 10471 [2]

ChemSpider 10039 [3]

Jmol-3D images Image 1 [4]

Properties

Molecular formula C30H60O2

Molar mass 452.46 g/mol

  (verify) [5] (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Melissic acid (or triacontanoic acid) is a saturated fatty acid.

EtymologyMelissic acid gets its name from the Greek word melissa meaning bee, owing to its abundance in the nectar of theflowers which attract bees.

Synthesisn-Triacontanoic acid was synthesized by Bleyberg and Ulrich (1931) and by G.M. Robinson.[6]

Self-assemblyTriacontanoic acid and triacontanamide (CH3(CH2)28-CONHI) can be self-assembled.[7]

References[1] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=506-50-3[2] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=10471[3] http:/ / www. chemspider. com/ 10039[4] http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC%28%3DO%29O[5] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=434945288& page2=%3AMelissic+ acid[6] Chibnall, Albert Charles; Ernest Frank Williams, Alfred Louis Latner, Stephen Harvey Piper (1933). "The isolation of n-triacontanol from

lucerne wax". Biochemical Journal 27 (6): 1885–1888. PMC 1253114. PMID 16745314.

Melissic acid 172

[7] Weinbach, Susan P.; Kristian Kjaer, Jens Als-Nielsen, Meir Lahav, Leslie Leiserowitz (May 1993). "Self-assembled Langmuir monolayersand trilayers at the air-formamide interface". Journal of Physical Chemistry 97 (20): 5200–5203. doi:10.1021/j100122a003.

External links• Melissic acid (http:/ / www. lipidmaps. org/ data/ LMSDRecord. php?LMID=LMFA01010030) at the Nature

Lipidomics Gateway

Article Sources and Contributors 173

Article Sources and ContributorsOil  Source: http://en.wikipedia.org/w/index.php?oldid=516528122  Contributors: (Didie), 007rex, 10jgwara, 123Hedgehog456, 28421u2232nfenfcenc, 4musicification, 5 albert square, A bit iffy,A930913, AVand, Abou Ben Adhem, Acather96, Access Denied, Across.The.Synapse, Addihockey10, Addshore, Ageekgal, Ahoerstemeier, Ahtih, Aitias, Alan Liefting, Alansohn, Aleenf1, AlexBakharev, Alex E. 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Triglyceride  Source: http://en.wikipedia.org/w/index.php?oldid=519645924  Contributors: Acornford, AirdishStraus, Alansohn, All Is One, Allens, Amore proprio, Anchoress,AnthonyQBachler, Anurag Garg, Arbitrarily0, Arcadian, Arkwatem, Armend, Atran Lab, AxelBoldt, BWernham, Bensaccount, BillBigfoot, Bomac, BrandonKuhl1979, Brian Sayrs, Bubba73,C.Fred, Can't sleep, clown will eat me, CaptainVindaloo, Choij, Clam0p, CliffC, Cmh, Corruptcopper, DaGizza, Danielle dk, Danny-w, DarkoV, Davidruben, Dcirovic, Dethroned Buoy, Djsasso,Donarreiskoffer, Drphilharmonic, Dusty relic, E0steven, Edgar181, Eham.a, Eric Yurken, Esperant, Ethridgela, Euryalus, Fconaway, Fluppy, Frankg, Frogular, FrummerThanThou, Funandtrvl,Gene Nygaard, Gilliam, Grandia01, Gruber76, Gurch, Guy Harris, HexaChord, Hexum, Hodja Nasreddin, Ibbn, Isnow, Istvan, Itecle, J.delanoy, Jag123, Jaganath, JeLuF, JeanneMish, Jeffq,JesseW, Jeversol, Jfdwolff, Jfloomis3, Joanjoc, JoannaSerah, Jpgordon, Jrtayloriv, Juliancolton, Justin W Smith, Kairos, Kazkaskazkasako, Kenmcl2, Killer666xxx5, Kilo-Lima, Kimiko,Kokkogdrit, Kpjas, KristinaHanspers, Ksheka, LEitK, La hapalo, Lagalag, Lapo3399, LeaveSleaves, Linas, Lwoauis, Lysy, MKar, Mac, Macboff, Magog the Ogre, Marek69, Marj Tiefert,Markp93, Marsku, Martian.knight, Maximus Rex, Mctt, Mey Pey, Michig, Mikael Häggström, Milkfish, Mimarx, Mlpearc, Musicality213, Mwhenson, N.hong.phuc, Nbauman,NewEnglandYankee, Nick125, Nishkid64, Nk, Nono64, Olivier, Openlander, ParticleMan, Patchouli, Permafrost, Pingveno, Popnose, Press olive, win oil, Pro crast in a tor, Professor malcolmwillis, PseudoSudo, Pushroll, Qocheedy daiin, Quang188, Radagast83, Reaper Eternal, Renato Caniatti, Rhorn, Rick Block, Rifleman 82, Roadnottaken, Rochellelim84, Rod57, Rogermw,RubyQ, Sadiq786, Sakkura, Scodocs2, SemperBlotto, Shenme, Sifaka, Skaaii, Smokefoot, Snigbrook, Stepa, Superccs, Supertouch, SvenAERTS, Svizac, Switchscribe, Taskualads, Taxman,Tempodivalse, The Rambling Man, Theamazingandy, They aside, ThomasWinwood, TimVickers, Tlesher, TonyRobinson787, Travis.Thurston, Tyciol, Verdy p, Versus22, WhatamIdoing,WolfmanSF, Xezbeth, Yekrats, زرشک, आशीष भटनागर, 337 anonymous edits

Cooking oil  Source: http://en.wikipedia.org/w/index.php?oldid=516831903  Contributors: A bit iffy, AThing, Ahoerstemeier, Alej420, Alphahealthproducts, Andycjp, Aoeuidhtns,AppetiteDynamo, Ask123, Bagatelle, Benjah-bmm27, Betswiki, Beve, Brentonboy, Bubba likes it, Bunchofgrapes, Burkhard.Plache, Burschik, Capricorn42, Catgut, Charon77, Chatool,Chemako0606, Chris Capoccia, Ckatz, ClairSamoht, CommonsDelinker, DRosenbach, Davewho2, Dbroadwell, DeBoisbaudran, DeadEyeArrow, Deepika.arya, Demekin, Dinesh smita,DocWatson42, Dori, Dounai, Download, E23, E8, Eleassar, Enote, Epastore, Eregli bob, Erianna, EricEnfermero, Esperant, Firsfron, Forcep caliper, Forteblast, FreplySpang, GB fan, GaiusCornelius, Gargaj, Gene Nygaard, Gentgeen, Geschichte, GetThePapersGetThePapers, Giftlite, Gloucks, Gnfnrf, Gobonobo, GraemeL, GrandIntel, Gzuufy, Hadal, Hazard-SJ, Hit bull, win steak,Hollywoodnorthreport, Hubba, Hyacinth, Iain turner, Ike9898, Imnotminkus, IvanLanin, J Raghu, J mareeswaran, Jahiegel, Jahnavisatyan, Jama lama, JennyRad, Jesus Cham, Jimp, JinzoClash,Jkaltes, JohnSankey, Joyous!, JulesH, Justlettersandnumbers, KVDP, Kanesue, Kenmcl2, Kilom691, KingRaptor, Lacrimosus, Lambanog, Landon1980, Larry laptop, Leodirac, Lisnabreeny,Lordtct, Lotje, Loveable bishounen, Luke088, LuoShengli, MPF, Macboff, Mani1, Marek69, Markaci, Marknesbitt, Materialscientist, MedicineMan555, Metron4, Mikael Häggström,Miller17CU94, Mion, Monoape, Moop stick, Moswento, Murgh, Mwtoews, NawlinWiki, Ndtodd84, Neilc, Nonky, Nutriveg, OffsBlink, Onorem, Otr500, Pekinensis, Peter, Philip Trueman,Pinethicket, PipingHotSoup, Polyparadigm, Ponydepression, Possum, Ppw0, Press olive, win oil, Processr, Randall Nortman, Randywilliams1975, RattusMaximus, RiceMilk, Rich Farmbrough,Rickholler, Rifleman 82, Rjwilmsi, Rmhermen, Rsl12, Sacramentoknits, Saephus, SaintCahier, Samoht21, Scouras, Shadowjams, Shadowofbeauty, Shenme, Sinus, Sjschen, Skizzik, Slyk22,Smaines, Smi0073, Snailwalker, Steamroller Assault, StephaneAubry, Switchercat, Taxman, Tb, The Magnificent Clean-keeper, Thomas Blomberg, Thumperward, Tizil, TruthinQuest, Ufiuza,Vanished user 2340rujowierfj08234irjwfw4, Veggieranger, Vellidragon, Waitak, WhisperToMe, Wiggy!, Wiki alf, Zidonuke, Zzxc, 335 anonymous edits

Vegetable oil  Source: http://en.wikipedia.org/w/index.php?oldid=520899371  Contributors: Abutorsam007, Acather96, Accurizer, Adrian J. Hunter, Alansohn, Alex Ex, Alex.muller, Alexandru Stanoi, Alexkin, Alfashturm, Allstarecho, Angr, Angus Lepper, Anjnathan, Annielogue, Anonymous Dissident, Antandrus, Arteitle, Aruton, ArwinJ, Avjoska, Baron von Chickenpants, Barticus88, Basawala, Bassbonerocks, Bejnar, Belg4mit, BenFrantzDale, BeverlyCrusher, Biju thounaojam, Blaxthos, Bloodstruck007, Bobblewik, Boccobrock, Bonadea, BorgQueen, Bovineone, BritishWatcher, Burschik, C. Mukherjee, CALR, CJ Withers, CWii, Calimo, Can't sleep, clown will eat me, Castoroil101, Charlesdmitchell, CharonM72, Chowbok, Chris Capoccia, ClairSamoht, Cmdrjameson, Cookiehead, Courcelles, Davemody, Dbroadwell, Dcherry3353, DeadEyeArrow, Dekimasu, Delldot, Der Eberswalder, Devonkime, Donald Albury, Doulos Christos, Downstream, Dthomsen8, E23, E8, ELNO Checking, Edgar181, Edward, Egmontaz, Epbr123, Erebus Morgaine, Erianna, Erpert, Excirial, Explicit, Extremecraig, Favonian, Forstnert, Fugyoo, Fuhghettaboutit, GB fan, Gadget850, Gaius Cornelius, Gene Nygaard, Gigemag76, Glenn, Goldenrowley, GorillaWarfare, Ground Zero, Gummer85, Gurch, GuruMinds, Hede2000, Helmoony, Hgrosser, Hraefen, Hubba, Huw Powell, Icairns, Incommand, Incrediblehunk, Irishguy, Istvan, JForget, JaGa, Jackj03, Jacob Bugge, Jacoemaritz, Jamesontai, JavierMC, JdeJ, Jeff G., Jim10701, Jimp, Jj137, Jm3, Jrtayloriv, Jrustenhoven, Judgepooley, Julesd, Jushi, Jusjih, Jytdog, Kakoui, Katalaveno, Kembarawan, Kirien, Knutux, Kraftykyle, Ksenon, L Kensington, LC.Lau, Lagrantierra, Lambanog, Larm93, Ldbio130, Lightdarkness, Lightmouse, Lignon, Lordandmaker, LotR, Luigizanasi, Lunchboxhero, MGTom, MONGO, Mac, Macy, Mahahahaneapneap, Makeemlighter, Marknesbitt, Marshman, MarthaHolley, Matt Gies, Matthewcgirling, Mccalliste53, Meeples, Mercurywoodrose, Midori, Mild Bill Hiccup, Mimaterials, Mindmatrix, Miranda, Mkweise, Mountainscout, Mrt3366, Mxn, Neelix, NellieBly, Nichalp, Noctibus, Nohat, Noles1984, Nono64, Nopira, Notheruser, Olivier, Paupamp, Pedro, Pekinensis, Philip Trueman, Pinethicket, Playadom, Ppntori, Prashanthns, Prgrmr@wrk, Pro crast in a tor, Pstudier, Qutezuce, Qwayzer, RaseaC, Reach Out to the Truth, Reaverdrop, RekishiEJ, Riceball, Rjwilmsi, Rmhermen, Rory096, Rror, SDC, SMC, SV Resolution, Scott Ritchie, Severo, Shoefly, Shreshth91, SilkTork, Silverchemist, Silverfish, SimonP, Sjschen, Skier Dude, Sminthopsis84, Solipsist, SomeHuman, Sparklingway, Spiritia, Stroppolo, TheGuruTech, ThePerpetualStudent, Thomas bonasera, Tjhiggin, Toh, Tom Lougheed, Tommy2010, Tommypark95, Tomr90, Transnistria,

Article Sources and Contributors 174

Treekids, Tresacl, Tropylium, Trusilver, Uziel302, V8rik, Vanderesch, Vincecate, Vuo, WLU, Waitak, Walor, Wavelength, Wertles, Whitebox, Wilibus, Woohookitty, WorthWhatPaid, Xdamr,Xnn, YOSF0113, Yobol, Youandme, Zbd, Zigger, Zzorse, 403 ,ماني anonymous edits

Fat  Source: http://en.wikipedia.org/w/index.php?oldid=519798874  Contributors: 01EnterShikari10, 09zoulzm, 124aplele124, 16@r, 7, A D 13, A Softer Answer, A.Cropley, AA, ATER1,Aaronb333, Aaronb3333, Academic Challenger, Accurizer, Achievement unlocked, Achilles.g, Acroterion, AdamM, Adashiel, Adbatstone, Afdsafeawt, Afrothunder69er, Ahoerstemeier,Airconswitch, Ajcfreak, Akamad, AkarraRks, Ale jrb, Alex.muller, AlexR, Alexf, Alfio, Ali, Allieyoyo, Alphachimp, AmericanIdolFreak22, Amherst99, Amitch, Amk26cap, AndPud, AndersTörlind, Andre Engels, Andrew Gray, Andrew Nutter, Andrewcmcardle, Andrewpmk, Angr, Ann Stouter, Anne72387, Anonymous Dissident, Anonymous anonymous, Antandrus, Anthere,Antonio Lopez, Arbiter117, Areuauser, Arghgh, ArglebargleIV, Ariel95, ArielGold, Arikado34, Arjun01, Arnson12345, Arronsj, Ashley280, Asianmang15, Astral Connection, Atrzcins,AuburnPilot, Aude, Autiger, Avnjay, Avraham, Az99, Aznspartan94, Azzurro2882, B, B1r2u doomsday, Baboon Faceless, Bachrach44, Baller2424, Banknote987, Barishnakof, Baritonemadness,Barliner, Barnrazer, Bart133, Basilbrushleo, Beaturnu, Beef091, Belg4mit, Bender248, Bendzh, Benmical619, Bensaccount, Bensteinert, Bexer, Beyondthislife, Bhadani, Bianca w123, BigCow,BigFatBuddha, BigNate37, Bigasian, Bigonee, Billx768, Bkalafut, Bkonrad, BlastOButter42, Blood Red Sandman, Blue bolt9, Bman19, Bmgoau, Bmicomp, Boa22, Bob 1210, Bobet, Bobo192,Bobsexual, Boffintim, Bongwarrior, Boothy443, Br77rino, Bradfordandrew, Brianga, Brimmerite, Brutulf, Bryan Derksen, Buchanan-Hermit, Buddah56, Buffgt, Bupkinmelissa, Byah me, CAJ,CTRAVAGLINO, Cactus.man, Caelitus, Calidore Chase, Calimo, Caltas, CalvinRocksMySocks, CambridgeBayWeather, Can't sleep, clown will eat me, CanadianCaesar, Canjth, Canucks69420,Carbuncle, Cassandralcoleman, Cate, Catsniff, CattleGirl, Ccacsmss, Ceyockey, Chalkwhite777, CharlotteWebb, Chaser, Cheeesemonger, CheesyCheesy, Cho Wei, Chris the speller,ChrisGriswold, Chrislk02, Christian75, Christopher Parham, Christy747, Chuck Sirloin, Chunky Rice, Ciaccona, Circeus, Cjohnl143, Cjwright79, Clayoquot, Clicketyclack, Closedmouth,Cmbcnbgvfgb, Cmdrjameson, Cmh, Cobaltbluetony, Cobozzo, Coffin, Cold-Susi, Condem, Conquestidor, Conti, Conversion script, Cool Blue, Coppertwig, Corpx, Corti, Corvus cornix,Cowboybebop23, Cowsarecool45, Cr0uch, Crawky7654, Crgreenwell, Crystallina, DJ Clayworth, DMacks, DRTllbrg, DSMeatte, DVD R W, DagnyB, Dambem, Dan D. 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Omega-6 fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=516228038  Contributors: AThing, Accurizer, Alexhangartner, Alfredo E., Angry bee, Blanchardb, Bork, Bradshej,ChemNerd, Coppertwig, Croscher, D.M. from Ukraine, Dananderson, David.Throop, Dcirovic, Deli nk, Dennis Brown, Drphilharmonic, Edgar181, Etribole, Fothergill Volkensniff IV, Frankg,Grandia01, Gyrofrog, Haus, Hydrargyrum, Jay L09, Jeffq, Jengod, JeramieHicks, Jon513, Jovianeye, Kenckar, Kitsunegami, Kjramesh, Koavf, Kupirijo, Lagrantierra, Lambanog, Leopard,LucioP, Madmagic, Mahemoff, Makanar44, Makeswell, Molbiolprof, Monsterparty, Morelipids, Next-Genn-Gamer, Onco p53, Panek, Plantsurfer, Pro crast in a tor, Queenoffats, RYNORT, RichFarmbrough, Rjwilmsi, Shaddack, Shevek, Shoefly, SidP, Slastic, Taxman, Tcncv, TeH nOmInAtOr, Teemu08, The Anome, The Real Marauder, Tide rolls, Toytoy, Tushayakovleva, Uncle Dick,Utcursch, Werson, Wikidsoup, Wikishotaro, Woohookitty, Xandi, YakbutterT, आशीष भटनागर, 107 anonymous edits

Omega-3 fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=520632371  Contributors: "alyosha", -Marcus-, 213.253.39.xxx, 213.253.40.xxx, AManWithNoPlan, AThing, AVand, AaronY, Abigailabbi, Ac1201, Access Denied, Aeluwas, AgentJ38, Ahmed Zawalaty, Alansohn, AlbertBickford, Alfredoefish49, Allens, Allonzy, AmateurHistorian, AmiDaniel, Andrew Dalby, Angel caboodle, Anomalocaris, Anthonyhcole, Aphilo, Apotek31, Aragorn2, ArcTheLad, Arny, Arthur Holland, Ascenta, Ashmoo, Aspro, AuburnPilot, Avaya1, Axl, Ayls, Balok, Barri Williams, Barticus88, Bartrossel, Beakerboy, Becritical, Belmond, Belovedfreak, Bendroz, Bennnh, Bertamo, Bigbeginner, BillFlis, BioPupil, BioTeX, Biosthmors, Blissfulpain, Bobblewik, Bobo192, Bork, Bovineone, Brettz9, BrianWilloughby, BrightStarSky, Brinerustle, Bstender, CLW, Cachedio, CambridgeBayWeather, Camden7, CanadianLinuxUser, Caroldermoid, Casby123, Catskul, Cbdeandc, Cbrouillette, Censlin, Cgd8d, ChangChienFu, Chaosmical, ChemNerd, Choij, Chowbok, Chris the speller, Christian75, Chronyx, Cirrus1024, Clampton, Common Man, ComplexEndeavors, ConstableX-2, Conversion script, Cookiehead, Coppertwig, Croscher, Cstaffa, Cstreet, Cuvtixo, D'n, D.M. from Ukraine, DBigXray, DRyan, DVdm, Dabuek, Daemondust, Dah31, DanKeshet, Dana boomer, Dave314159, David.Throop, Davidbengtenglund, Davidruben, Dbfirs, Dbroadwell, Dchristle, Dcirovic, Dcooper, Deb, Deli nk, Delldot, Delta474, Diblidabliduu, Diderot's dreams, Digital infinity, Discospinster, Dmarshiee, Dodger67, Dolomin, Dolphin29, Domino42, Douglasccollins, Dougofborg, Downwithscurvy, Dpmsurf, Dr. Morbius, Dragonhorse1, Dreamyshade, Dreslough, Drphilharmonic, Dryman, Edgar181, Edward, EffeDi, Ehn, El3ctr0nika, Electron9, Elvey, Emote, Epgui, Epipelagic, Erianna, Ericurs, EspirituSanto, Eteune, Etribole, Eubulides, EvelinaB, Eveningmist, Evice, Fact check, Facts707, Fadix, Fashionstay, Fences and windows, Feyfoys2001, Ffarahf, Flandrensis, Flavonoid, Flaxdoctor, Flaxfan, FlyingToaster, Foobaz, Francis Lima, Frankg, FranklinDelanoBluth, Fredrik Stal, Frentz, FreplySpang, Fyrius, Gaius Cornelius, Garkbit, Gharmon, Giftlite, Gigemag76, Gimmetrow, Gladlax, GlassLadyBug, Goldom, Gon-no-suke, GraemeL, Grando, Groliver, Gronky, Guaka, Gunnar Larsson, H, H Bruthzoo, HMman, HaidaHalibut, Handlebarman, Happy Dragons Press, Hdante, Headbomb, HealthUK, Healthbm, Hersfold, Hgrosser, Holme053, Holme215, Horoporo, Howcheng, Huangdi, HumphreyW, Icairns, Icek, Immunize, ImperfectlyInformed, InfoCan, Informer18, Iridescent, Iskunk, Istvan, Iterator12n, J.P.Lon, JLdesAlpins, Jaknouse, Jamesmorrison, Jannex, Jay L09, Jbundschu, Jclerman, Jeffbarnett513, Jeffrey O. Gustafson, Jengod, JeramieHicks, Jeremiah, Jesanj, Jessie489, Jfdwolff, Jhay116, Jim1138, Jjamison, Jmh649, Jo3sampl, John Hill, JohnSRoberts99, JohnSankey, Johnatx, Johner, Johnteslade, Joriki, Jsr1234, Julesd, Justarandomperson, Justin W Smith, Karada, Kazvorpal, Kbatten326, Kenckar, King of Hearts, Kirkite, Kittybrewster, Koavf, Kupirijo, LAEsquire, Lambiam, Langhorner, Laurascudder, Leopard, LilHelpa, Linas, Linda Martens, Ljmdrfc, Localzuk, Longinus876, Lonwolve, LostLeviathan, Lova Falk, LucioP, Luís Felipe Braga, Lykoped, M.thoriyan, MBC2011, MER-C, Mack2, Macrakis, Makeswell, Mako098765, Makwy2, Malljaja, Marcelo1229, Mardus, MarkTAW, Markhampton, Martinpassmore, Matchups, Mattbr, Matthardingu, MattieTK, Matturn, MaxHund,

Article Sources and Contributors 176

MaxS 33, Mcvfloyd, Md8519, MedicineMan555, Medos2, Merideth, Mhardcastle, Michael Daly, Michaeldsuarez, Midgetimpinger, Mig77, MightyWarrior, Mike411, Milk, Miller17CU94,Minimac's Clone, Modify, Molbiolprof, Mr.Z-man, MrOllie, Mufka, Mulgul, Munakata, Muthuveerappan, N3362, Nageh, Nasif123, NathanBeach, Nathanael Bar-Aur L., Nbauman,Nealcardwell, NessieVL, Neuroscientist28, Nevit, Newbeenew, Nick Drake, Ninja Wizard, Nol888, Nono64, NorthernThunder, Nu2004, Nunquam Dormio, NutrisaurusRex, O1villalon,Oblivion, Octahedron80, Ohnoitsjamie, OlafBaumgartner, Olivierd, Omegatron, Open2universe, Orangemarlin, Osua84, Oxymoron83, PWSMom, Pakaraki, Parker007, Parsifal, PatrickFisher,Paul gene, PeaceLoveHarmony, Pearle, Philip Trueman, PierreAbbat, Pipedreambomb, Pjrm, Pocahontasboricua, PranksterTurtle, Président, PumpkinT, Qooth, Quarl, RBBrittain, RDBrown,RHaden, RJFJR, Ram-Man, Rapscallion, Rbbevan, Reach Out to the Truth, Rememberway, Researchman1964, RexNL, Reydeyo, Rich Farmbrough, Richard Arthur Norton (1958- ), Ricklaman,Rjwilmsi, Rod57, Rogermw, RollandWaters, Roofpig, Rrika, Rthrelfall, RussellcurtisIH, Ruth Michaels, S0610086, SJaneM, Saintswithin, Samy23, Sander123, Sannse, Sbosque, Schnarr,Scholarch, ScottyBerg, Sebastiano venturi, Seipjere, Sfahey, Shaddack, Shadowjams, Shevek, Shipmaster, Sholtesr, Siixusa, Sijo Ripa, Skater, Skintreatment, Slakr, Slashme, Slvrvet, Smboyan,Soapypigeon, Sobreira, Sonicology, Spiff, Srtxg, SteinbDJ, Stephenb, SteveCrook, Steven5096, Stevenfruitsmaak, Stridb, SummerPhD, SusanLesch, SweetP112, Szmahoon, Taxman, TeHnOmInAtOr, Tea with toast, Thatphotoguy, The Anome, The Banner Turbo, TheDarknessVisible, Thumperward, Timotab, TitaniumDreads, Tito4000, Toh, Tomcorsonknowles, Tonytypoon,Toytoy, Tree Biting Conspiracy, Trek00, Trevj, TrevorX, Trevyn, TreyHarris, Tristanb, Trlkly, Troephe, TyA, Umofomia, Urania3, VBGFscJUn3, Vanished user 5zariu3jisj0j4irj, Vbs,Venkatzmail, Verdy p, Vespa07, Victor Engel, Viriditas, Virtualt333, Vl'hurg, Volume1, Vranak, Vsmith, WAS 4.250, WDavis1911, WLU, Wahoofive, Wanderer099, War3rd, Webbster,Wemlands, Werson, WhatamIdoing, WhirlwindChemist, Widefox, Windows.dll, Wingedsubmariner, Wlswardf, WriterHound, Xris0, YDZ, Yippygroup6, Zad68, Zefr, Zip77, Zottemie, आशीषभटनागर, 1172 anonymous edits

Omega-9 fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=517254209  Contributors: Accurizer, AgentPeppermint, Antandrus, Bob Stein - VisiBone, Chemacb, Curb Chain, D,David.Throop, Dcirovic, Drphilharmonic, Edgar181, Hgrosser, Istvan, Jack122064, Jengod, JeramieHicks, Kenckar, Kupirijo, Lagrantierra, Musashi, Pelirojopajaro, Pipedreambomb, RDBrown,Radon210, Rosarinagazo, Sensonet, Shaddack, Slastic, TeH nOmInAtOr, That Guy, From That Show!, WLU, Wdflake, Werson, Xandi, Zephalis, 35 anonymous edits

Fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=520655837  Contributors: - ), 1m y0ur targ, 5 albert square, 5604a, Abeg92, Accurizer, Addshore, Ahoerstemeier, Albmont,Alexhangartner, Alsocal, Andonic, Angela, Animum, Antandrus, Anupamsr, Arcadian, Aunt Entropy, Aznshark4, BTOperator150, Bassy101, Belgrano, Belovedfreak, Bencherlite, BernardH,Blethering Scot, Bobblewik, Bogey97, Bongwarrior, Bryan Derksen, Btmachine333667, Bubbha, Bugo30, Bustinout244, C.Fred, CMBJ, Carlquinn, Carynoid, Cburnett, Cheeesemonger,ChemGardener, ChemNerd, Chiros Sunrider, Christian75, Chuckyack, Cigaro Pizarro, Cindylovesyou, Clarince63, Cmh, Coltj1397, Conversion script, Corbinkirbynewtonscooby22,Cremepuff222, Cyrushehe, DA3N, DSLeB, DamnitFace, Dante Alighieri, Darklilac, DarkoV, Dave6, Davewho2, David.Throop, Davidresseguie, Dawnseeker2000, Dcirovic, Deli nk, Delta G,DennyColt, Diderot's dreams, Discospinster, Djk3, Domenic16, Domstaz, Donarreiskoffer, Doulos Christos, Download, DrGabriela, Dreadstar, Drmies, Drphilharmonic, Dsnow75, Ebuxbaum,Edgar181, Elkman, Epbr123, EryZ, Ewisely, Excirial, FF2010, FMephit, Fabiform, Famas96, Fedir, Fieldday-sunday, Footwarrior, Frankg, Frecklefoot, Fæ, G00nsf, G3pro, GB fan, Gabethenerd,Gcanyon, GenOrl, Ghosts&empties, Giftlite, Glane23, Glenn, Gordoniscoolerthancorinne, Gracenotes' left sock, Greensburger, Hargan, Haripandit, Hasinaisdabest, Hgrosser, Hsart, Ibrahimlodhi, Icairns, Icek, Ike9898, Ilikeeatingwaffles, ImperfectlyInformed, InfoCan, Istvan, J G Campbell, J.delanoy, JDog Sassy Pants, Jag123, Jaganath, Jay L09, Jaysbro, Jbening, Jdude89,Jfdwolff, Jim1138, Jmrowland, Joe Jarvis, JoeAnderson, John, Johner, JohnnyA54, Johnsmith12321, Jpmoser14, Jqavins, Jü, Karenjc, Karol Langner, Khukri, Kosigrim, Kristof vt, Ksero,Kukini, Kupirijo, Kutulu, Lagrantierra, Lancethex, Lars Washington, Linguina, Lubricatedcondoms, Luminaux, Lupin, Mac, Magioladitis, Mandarax, Manke20, Mannafredo, Mar Garina,MarcoTolo, Marcushen3ryal, MastCell, MatthewEHarbowy, Mentifisto, Mikael Häggström, Mike Biker, Mike713, Miller17CU94, Minesweeper, Modernist, MoleculeUpload, Molybdenumblue,Mozzerati, Muhandes, Muriel Gottrop, N3362, NawlinWiki, Nbauman, Nicholasmorassutti, Nicklink483, Nikai, Northfox, Numbo3, Nutriveg, OM-Aleks, Odazi, Odie5533, Oiws, OldMoonraker, Patelurology2, Pcyrus, Pedant, Peterlin, Phil Boswell, Phil Ian Manning, PierreAbbat, Pinethicket, Press olive, win oil, Prestonmag, Pro crast in a tor, Prolog, Quantockgoblin,Queerboy1234, Quelsen, R107, RYNORT, Rajasekhar1961, Randi barnes 2013, Reaper Eternal, Rej5y7, Riccardo.fabris, Rich Farmbrough, Richard Arthur Norton (1958- ), Rjwilmsi,Robertvan1, Ronhjones, Royote, Rror, SEWilco, SabrehamLincoth, Salsb, Sasata, Scarredintellect, Scott English, SemperBlotto, Several Pending, Sexualala, Shaddack, Shadowjams,Shadowlapis, Shirulashem, Shoy, Slashme, Smokefoot, Snaffu, Snek01, Snigbrook, Snowmanradio, Snowolf, Sole Soul, Souperbwitch, Spartan-oj, Spikey, Spinningspark, Starblind,StevenLcarroll, Stone, Sundstrj, Sweikart, THEN WHO WAS PHONE?, Tangent747, Taroaldo, Taskualads, Taxman, TeH nOmInAtOr, The Anome, The Thing That Should Not Be, The wub,Theda, ThereIsNoSteve, Timwi, Tristanb, Uthbrian, V8rik, Vainamainien, Vbs, VernoWhitney, Vikky2904, Waitak, Wavelength, Wayne Slam, Werson, Why Not A Duck, Wickey-nl, Wiki alf,WikipedianMarlith, Winchelsea, Worth my salt, Wt222, Ww, Yyy, Zackfield100, Zwyciezca, 509 anonymous edits

Essential fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=510398114  Contributors: "alyosha", Accurizer, Alfredo E., Arcadian, Arthur Blake, BarryNorton, Benbest, Bendroz,BorisVM, Bork, Brian0918, CLW, Cbailey7, ChemNerd, Choij, Chris Capoccia, Chrisonwiki, Cmdrjameson, Cmh, CommonsDelinker, Coppertwig, Cremepuff222, DARTH SIDIOUS 2,DabMachine, David.Throop, Dcirovic, Deli nk, Diberri, Dpmsurf, Duplode, Ebeitel, Edgar181, Eequor, Eno-ja, Eperotao, Eregli bob, Espoo, Evalfyrst, Frankg, GB fan, Gaius Cornelius,Ghosts&empties, Guaka, Hakapes, HappyM, Haripandit, ImperfectlyInformed, Iroony, Istvan, J.delanoy, Jesanj, Jfdwolff, JohnSankey, Kaesque, Kaiser matias, Kilom691, Klubbit, Kosigrim,Kundor, Lagrantierra, Lindum, LizGere, LucioP, MGAgro, Mako098765, Mastercampbell, Michael Hardy, Michaplot, MightyWarrior, Miller17CU94, Nbauman, OccamzRazor, Ohnoitsjamie,Perkeleperkele, Pikiwyn, Pollinator, Pro crast in a tor, Rajasekhar1961, Rhlozier, Richard Arthur Norton (1958- ), Rifleman 82, Rjwilmsi, Rod57, SDS, Sango123, Sardanaphalus, Sbharris,Scarlett-ann, Scemil, Sigh Ns, Silversin, Slick12, Smokefoot, Stlblufan, Stupefaction, T-borg, T0mpr1c3, Takometer, TeH nOmInAtOr, That Guy, From That Show!, The Anome, The High FinSperm Whale, The bellman, TimVickers, Time9, Tito4000, TonyClarke, Tothebarricades.tk, Tropicanahouse, Tyciol, Una Smith, Vanderesch, Vbs, Wdfarmer, Wideshanks, Xvazquez, Yaush,Yobol, Zeifgeist, حسن علي البط, आशीष भटनागर, 133 anonymous edits

Interesterified fat  Source: http://en.wikipedia.org/w/index.php?oldid=514844966  Contributors: AThing, Alphachimp, Badagnani, Beetstra, Bhadani, CMBJ, Clyde.cutting, David.Throop,Dcirovic, Discospinster, Gpgrazioli, Inhumandecency, Istvan, Jim10701, LeadSongDog, LeendertW, LilHelpa, Marek69, MaxPont, Melchoir, PDH, Pauli133, Pelirojopajaro, Prakash Nadkarni,Rjwilmsi, Roadnottaken, Schmancy47, Unfree, Woohookitty, Ὁ οἶστρος, 34 anonymous edits

Short-chain fatty acid  Source: http://en.wikipedia.org/w/index.php?oldid=519350851  Contributors: Arcadian, Belgrano, Calvero JP, Dcirovic, Drphilharmonic, Edgar181, Emmanuelm,Flamgirlant, JohnnyA54, Koavf, Ksero, Mikael Häggström, Pro crast in a tor, R. S. Shaw, Welsh, Whoop whoop pull up, Wickey-nl, YUL89YYZ, 13 anonymous edits

Palmitoleic acid  Source: http://en.wikipedia.org/w/index.php?oldid=515074489  Contributors: 570ad, Arcadian, Balcer, Beetstra, Blind cyclist, Boing! said Zebedee, Chem-awb, Christian75,DSLeB, Dcirovic, Edgar181, Elkman, Istvan, Jaguarlaser, Julia Rossi, Jusdafax, LesTP, Meric.altinoz, Mwtoews, NEUROtiker, Pelirojopajaro, Pgk53, Rej5y7, Rich Farmbrough, Rifleman 82,Samsara, Slashme, Smulthaup, The chemistds, Trang Oul, Volume1, Zefr, आशीष भटनागर, 46 anonymous edits

Myristoleic acid  Source: http://en.wikipedia.org/w/index.php?oldid=511735705  Contributors: Akane700, Cburnett, Chem-awb, Dirac66, Edgar181, Justinlwilson, The chemistds

Oleic acid  Source: http://en.wikipedia.org/w/index.php?oldid=515959904  Contributors: 83d40m, Albmont, Apple2, Arcadian, Banus, Beetstra, Belovedfreak, Bender235, Benjah-bmm27,Biscuittin, Boky, Bracodbk, Capricorn42, Cesium 133, Ceyockey, Chad Van Schoelandt, Chem-awb, ChemNerd, Clemwang, Daniel,levine, Dave Heenan, Dbroadwell, Dcirovic, Dirac66,Drandrefrancis, DrippingGoofball, Edgar181, Edsanville, Ehsankhan01, Eliteclan, Ezhiki, Gaius Cornelius, Gene Nygaard, Ghosts&empties, Giftlite, Grandia01, Hdfart, Hegh, Itub, J306,JForget, JStiller13, JiVE, JillEvans74, Jmeppley, Kidkidpie2, Le K-li, LeadSongDog, Leništudent, Leolomba, Leopard, Louisajb, Mar Garina, Matt Fitzpatrick, Mellery, Michalpech, Mikespedia,Mozzerati, NS Zakeruga, Nirmos, Niteowlneils, NotWith, Nstott, Olivier, Oxford Dictionary, Paul144, Peterlewis, Rees11, Rhode Island Red, Rjwilmsi, Rod57, ScAvenger lv, Shaddack,Shanata, Shinkolobwe, Slashme, Sleddog116, Smokefoot, Spiral5800, Supspirit, THEN WHO WAS PHONE?, Timotheus Canens, Tophatdan, Twir, TylerDurden8823, Una Smith, User2004,VPliousnine, Vballoon, VikOlliver, Volume1, Vssun, WaysToEscape, Will Beback, WriterHound, Xxxx00, Ywaz, Σ, Александър, 85 anonymous edits

Sapienic acid  Source: http://en.wikipedia.org/w/index.php?oldid=510813301  Contributors: Edgar181, Fences and windows, Smulthaup, The chemistds, Yikrazuul, に ょ ろ ん, 1 anonymousedits

Elaidic acid  Source: http://en.wikipedia.org/w/index.php?oldid=519187397  Contributors: Akane700, Baronnet, Beetstra, Benjah-bmm27, Buggia, Chem-awb, Daniel,levine, David.Throop,Dcirovic, Edgar181, Elkman, Eric-Wester, Icek, Kauczuk, Magioladitis, Plasmic Physics, Rees11, ScAvenger lv, 4 anonymous edits

Vaccenic acid  Source: http://en.wikipedia.org/w/index.php?oldid=518487053  Contributors: Beetstra, Boghog, Cgingold, Chem-awb, David.Throop, Dcirovic, Edgar181, Elkman, Frankg,HappyCamper, Hmains, Istvan, Jynto, LUIS SUAREZ LOPEZ, Ldeder01, Rifleman 82, Rjwilmsi, Shawnc, Smulthaup, The chemistds, 17 anonymous edits

Linoelaidic acid  Source: http://en.wikipedia.org/w/index.php?oldid=519183882  Contributors: Beetstra, Chem-awb, Edgar181, Icek, Plasmic Physics, Rifleman 82

Linoleic acid  Source: http://en.wikipedia.org/w/index.php?oldid=519042229  Contributors: 570ad, Aecis, Albmont, Alexhangartner, Ambix, Arcadian, Arctic Night, BD2412, Barkeep, Beetstra,Bender235, Benjah-bmm27, Bform, Bgsibbitt, Blinkomom, Bogwhistle, Bposert, Brettz9, BroderickAU, Capricorn42, Carmody70, Ceyockey, Chem-awb, ChemNerd, Chesnok, Choij,Christian75, Coppertwig, Curlypaul924, DarkoV, Davewho2, David.Throop, Dcirovic, Den68cube, Docu, Earthdirt, Edgar181, Frankg, Ghosts&empties, Gigemag76, HenkvD, Icek, J306, JayL09, JiVE, Karin D. E. Everett, Kusunose, La goutte de pluie, Leyo, LittleHow, Logan Rutherford, Mac Davis, Mmoneypenny, Mozzerati, NotWith, Nwbeeson, Osm agha, PFHLai, Panos AGR,Pbfpfoss, Pekinensis, Pilotguy, Pinethicket, Pjstewart, Pro crast in a tor, Quarknimble, Raykeller, Rej5y7, Rhø, Rich Farmbrough, Rifleman 82, Rjwilmsi, Rod57, Romney, ScAvenger lv,Shaddack, Slashme, Smokefoot, Spierobi, Stone, Swimmerguy13, TheKMan, Tricky Wiki44, Una Smith, Vsmith, WWW2011, Woohookitty, Words in sanskrit, WriterHound, Xetxo, Yalbik, Δ,आशीष भटनागर, 120 anonymous edits

Arachidonic acid  Source: http://en.wikipedia.org/w/index.php?oldid=518208129  Contributors: Aeternitatis, Arcadian, Ask123, Axl, Beetstra, Benbest, Bender235, Bobber0001, Bogwhistle, Brettz9, Celian, Chem-awb, ChemNerd, Chris Capoccia, Clemwang, Clovis Sangrail, Cobalamina, Cohesic, Colonies Chris, Coppertwig, Daen, Damianemmanuelphun, David.Throop, Dcirovic, Delldot, Diberri, Drphilharmonic, Edgar181, Eno-ja, Falcon8765, FrankMJohnson, Frankg, Fuzzform, Giftlite, GregorB, Immunize, Inanefx, Jamisonhalliwell, Jfdwolff, Johner, JorisvS, Jü,

Article Sources and Contributors 177

Khoikhoi, Kummi, Kwamikagami, Leopard, Louisajb, LucioP, Mako098765, Mani1, Mikael Häggström, Miniyazz, Nunquam Dormio, PKT, Plasmic Physics, Pridonwa, Quickmythril, Rifleman82, Rjwilmsi, ScAvenger lv, Semolo75, Shaddack, Shadowlapis, Signalhead, Stefeyboy, Stepa, SubDural12, Taxman, Tea with toast, The Anome, Tristanb, Trusilver, Unfree, Virulent 78, Wllewellyn, Yikrazuul, Zenguyuk1, 78 anonymous edits

alpha-Linolenic acid  Source: http://en.wikipedia.org/w/index.php?oldid=520113371  Contributors: Arcadian, Avanhorn, Beetstra, Benjah-bmm27, Bobjgalindo, Brossow, Ceyockey,Chem-awb, ChemNerd, Chowbok, ChrisRainy, Christian75, Clemwang, Colonies Chris, Coppertwig, Czarkoff, DT Isaak, David.Throop, Dcirovic, Drphilharmonic, Edgar181, El C, Eloerc,Fconaway, First Light, Frankg, Fvasconcellos, Gaius Cornelius, Ge0nk, Gigemag76, Headbomb, HenkvD, Ilmari Karonen, Istvan, Jag123, James Crippen, JohnElder, Jorgenumata,JosephCampisi, Karen Johnson, Kupirijo, La goutte de pluie, Luís Felipe Braga, Michael Devore, Michael Hardy, Micpol, Nutriveg, Nwbeeson, Ohconfucius, Plantsurfer, Polon11, Pro crast in ator, Rhetth, Rich Farmbrough, Rifleman 82, Rjwilmsi, Sam Korn, Shaddack, Shadowjams, Shadowlapis, Showjumpersam, Slashme, Sliggy, Sohale, Sparkie82, ThomYoung, Tjmj, Toytoy,TylerDurden8823, Vstarsky, Vuo, Werson, WriterHound, Yefi, Zefr, आशीष भटनागर, 111 anonymous edits

Eicosapentaenoic acid  Source: http://en.wikipedia.org/w/index.php?oldid=518076891  Contributors: AManWithNoPlan, Arcadian, Avaya1, Beetstra, Bento00, Bobjgalindo, BugzPal,Chem-awb, ChrisHamburg, Christian75, Chuckwolber, Clemwang, Colonies Chris, Coppertwig, Dabuek, Danfa1971, David.Throop, Davidbengtenglund, Dcirovic, Drphilharmonic, Edgar181,FT2, Gaius Cornelius, Ger-k, Ghosts&empties, Gronky, Hgrosser, Horoporo, J.delanoy, J306, Jaerik, Jesanj, Jimbo Mahoney, Jmh649, JoeyDay, Johner, JorisvS, Justin W Smith, Keenan Pepper,Kristina Walter, Lamro, Leshiy uk, Lilac Soul, Lionelbrits, LucioP, MBC2011, Mailer diablo, Maquesta, Markaci, MastCell, N-k, Nirmos, Oda Mari, RDBrown, Rifleman 82, Rjwilmsi,Shaddack, Snori, Stepa, SubDural12, Suradnik50, Tjmj, WriterHound, Ww, 65 anonymous edits

Erucic acid  Source: http://en.wikipedia.org/w/index.php?oldid=520287885  Contributors: Aelffin, Arcadian, Archaeogenetics, Aspro, AxelBoldt, Beetstra, Ben Ben, Bender235, Bhadani,BritishWatcher, Bwats2, CBM, Chem-awb, ChemNerd, Clemwang, Czarkoff, David.Throop, Dragunova, Drphilharmonic, Edgar181, Elkman, Ericsheldon, Eyu100, Gigemag76, Gluo88,Goethean, Greg L, Grendelkhan, Guanaco, Guy Harris, Harblybarbly, Hgrosser, Hoffmeier, Hydrargyrum, Inter, Jacopo Werther, Jasonwithey, John salmon, JohnI, Jrdioko, Kocio, Marcelivan,Maximus Rex, MichaelClair, Middle 8, NetRolller 3D, Novangelis, Petersracing, Physchim62, Pustelnik, Qaddosh, RDBrown, Raeky, Rex Yellowstone, RiceMilk, Rich Farmbrough, Rjwilmsi,Saintrain, ScAvenger lv, Secretlondon, Securiger, Sesna2, Shaddack, Sisterdetestai, Smokefoot, Sobolewski, Spyderchan, SunnyInHouston, Sweikart, T0mpr1c3, WLU, Wcoole, Wikiscottcha,Works of Sweat, WriterHound, Writtenright, Xenophon777, YUL89YYZ, Ylem, Zombiejesus, 64 anonymous edits

Docosahexaenoic acid  Source: http://en.wikipedia.org/w/index.php?oldid=520758876  Contributors: 5Q5, 82squaremetres, Amakuha, Amityshatraw, Anthonzi, Arcadian, Arthurfragoso,Beakerboy, Beetstra, Bobwmontgomery, CWatrous, Chem-awb, ChemNerd, Christopher140691, Clearlight418, Coppertwig, DMacks, Damianemmanuelphun, Danielle dk, David.Throop,Dcirovic, Deli nk, Diberri, Dr.saptarshi, Drphilharmonic, Dyfsunctional, Eastmain, Edgar181, Elemeno, Enix150, Eno-ja, Epipelagic, EricWesBrown, Frankg, Fred Bauder, Gaius Cornelius,Gardenerlynn, Ghosts&empties, Gigemag76, Goldom, Goorky, Greensburger, Griffinofwales, Happymercury, HighestSources, Horoporo, Hu12, ImperfectlyInformed, Istvan, J G Campbell,J.delanoy, Jasonwithey, Jbundschu, Jcarabal, Jeffman54, Jerome Samson, Jmcc150, Jmh649, John of Reading, Johner, Jokestress, JorisvS, Justin W Smith, Khazar, Klubbit, Krefts, Lectonar,Legion fi, LinkinPark, MAKSEN, MBC2011, Marco Polo, Mikepesky, Mmd249, Moilleadóir, MrOllie, N-k, NathalieDory, Nk, Nunquam Dormio, Pickertj, Plasticup, Pol098, Qrsdogg,Quickmythril, Quizkajer, Rhjc2, Rich Farmbrough, Richiez, Riogray123, Rjms, Rjwilmsi, Sapphic, Sbharris, ScAvenger lv, Scott English, Shaddack, Shimon Yanowitz, StephenWeber,Suradnik50, Sweikart, Tea with toast, Thetraytiger, ThinkPatrick, Timlev37, Torsolo, Tryptofish, Unfree, Verytas, VivekVish, War3rd, WikiWikiPhil, Wmahan, Wolfch, Woohookitty,WriterHound, Wwphd, Zefr, 148 anonymous edits

Caprylic acid  Source: http://en.wikipedia.org/w/index.php?oldid=517281706  Contributors: AED, Albmont, Arcadian, Beetstra, CJ DUB, Calvero JP, Carabinieri, Casforty, Cbsmall1,Chem-awb, ChemNerd, Dcirovic, Edgar181, Fram, Gor n bein, Hellbus, HenkvD, Hgrosser, I.Sáček, senior, Itub, Jynto, Keenan Pepper, Kupirijo, Linnormlord, Mmortal03, Mongreilf, MusicalLinguist, Mysid, Niels Olson, Nuklear, Physchim62, Pinktulip, Romney, ScAvenger lv, Sloth Loves Chunk, Sticky Parkin, Vernon60, Where next Columbus?, Xtabay, 13 anonymous edits

Decanoic acid  Source: http://en.wikipedia.org/w/index.php?oldid=517801066  Contributors: Arcadian, Beetstra, Calvero JP, Chem-awb, ChemNerd, Choij, Darkstriker, Dcirovic, Dfrg.msc,Edgar181, Eras-mus, Hans Frörum, Hellbus, IByte, J G Campbell, Jed 20012, Jfurr1981, JohnSRoberts99, Jynto, Karol007, Keenan Pepper, Marysunshine, Meodipt, Papipapipya, Physchim62,Pvosta, Rajasekhar1961, Rmosler2100, ScAvenger lv, Schizmatic, Smokefoot, Space Cadet, Uthbrian, 15 anonymous edits

Lauric acid  Source: http://en.wikipedia.org/w/index.php?oldid=510229077  Contributors: ACW, Alansohn, Almost-instinct, Annalise, Antilock, Arcadian, BD2412, Badagnani, Beetstra,Benjah-bmm27, Benjamindees, Blamblamblam, Bluer6, Cburnett, Chem-awb, Clfranklin4, Daronn22, Dcirovic, Diderot's dreams, Drphilharmonic, Dsence, Ec-, Edgar181, Edsanville, Elkman,Eras-mus, Excirial, Frankg, Frap, Ghosts&empties, Ginsengbomb, Husond, Jay L09, Juliancolton, Katalaveno, Keenan Pepper, Killiondude, Lambanog, LilHelpa, Louisajb, Magic cigam,MarkSutton, Materialscientist, Metafunk, Michael Anon, Michael Bailes, Mmortal03, MoleculeUpload, Mr Accountable, Mschel, Nemu, NeoJustin, OccamzRazor, Paulinboots, Pdacortex, PeterG Werner, Physchim62, RYANcummings, Rajasekhar1961, Rangek, Rich Farmbrough, Rifleman 82, Rjwilmsi, ScAvenger lv, Seidenstud, Shaddack, Shotwell, SidP, Siegaard, Sloth LovesChunk, Smokefoot, Softball998, TehBrandon, The Thing That Should Not Be, The chemistds, The wub, Thricecube, Trince, Trusilver, Wmahan, WoodenTaco, YOSF0113, Yamaguchi先 生,Yobol, Zaxxon de, आशीष भटनागर, 145 anonymous edits

Myristic acid  Source: http://en.wikipedia.org/w/index.php?oldid=506881056  Contributors: Almost-instinct, Arcadian, Beetstra, Benjah-bmm27, Bluemoose, Chem-awb, Dcirovic, Diderot'sdreams, Edgar181, Elkman, Emmanuelm, Firehouse123, G.hartig, Gettingtoit, Informer18, JiVE, Jonathanischoice, Keenan Pepper, Leptictidium, Louisajb, Marcika, MrBell, N.hong.phuc,NawlinWiki, Nutriveg, P3Pp3r, Physchim62, Rajasekhar1961, Rosarinagazo, ScAvenger lv, Semolo75, Shaddack, The chemistds, 25 anonymous edits

Palmitic acid  Source: http://en.wikipedia.org/w/index.php?oldid=520755484  Contributors: Adrian.benko, Alan Liefting, Alansohn, Alexbateman, Andy M. Wang, Arcadian, AtonX, Avoided,Beetstra, Bellybutton Lint, Bggoldie, Boloneyboy is awsome, BorisTM, Chem-awb, CountZepplin, David H. Flint, David from Downunder, Dcirovic, DeffIR, Delta G, Diderot's dreams,Dogtownman, Drphilharmonic, Edgar181, Elkman, Eras-mus, Fundamentisto, Georgiabiker, Ghosts&empties, Gigemag76, IngerAlHaosului, J306, JLSeidman, Jay L09, Jeltz, Jemmy Button,Joanjoc, JohnSRoberts99, Keenan Pepper, LeadSongDog, LesTP, Louisajb, Lysy, Markussep, Michael Hardy, Mmortal03, Moshe Constantine Hassan Al-Silverburg, Mr Accountable, Ocdnctx,Rmky87, Rod57, Rui Gabriel Correia, ScAvenger lv, Shaddack, Smokefoot, Speen23, Stormhelm, The Transhumanist, Tooga, Toytoy, TranscendTranslation, Ugen64, VPliousnine, VSimonian,Vossman, WriterHound, X-mass, Xslim24x, Xxxx00, Zodon, Александър, 60 anonymous edits

Stearic acid  Source: http://en.wikipedia.org/w/index.php?oldid=520656773  Contributors: Ahoerstemeier, Ajshm, Alansohn, Albmont, AlfSmaster, Arcadian, Arkie-annie, Atemperman,Atubeileh, Bbartlog, Beetstra, Blahblahblahblahblahb, Bobo192, Borgdylan, Bracodbk, Chem-awb, ChemGardener, Circeus, Cool3, Crazycomputers, Darklilac, Dcirovic, Delta G, Devon Fyson,Dick Bos, Diderot's dreams, Dirac1933, Drphilharmonic, Edgar181, Edsanville, Eli the Bearded, Epbr123, Excirial, Frankg, Georgelazenby, Ghosts&empties, Gigemag76, Ginsengbomb,GorillaWarfare, Gyrofrog, Gökhan, Hadal, Hellbus, Heron, Hibikitour, Iantresman, J306, JiVE, Jmundo, KDS4444, Keenan Pepper, Leonard G., Louisajb, MWAK, Materialscientist, Matt18224,Mauler90, Mboverload, Miaow Miaow, Mpulier, Neverquick, Niceguyedc, Nirmos, NotQuiteSanity, Nsteinberg, Nstott, Nutriveg, Nv8200p, Pdcook, Pelirojopajaro, Pikiwyn, Pinethicket,Quinsareth, Rawnoodles10, ScAvenger lv, Seav, Shaddack, Siegaard, SiobhanHansa, Slashme, Slicedoranges, Smokefoot, Soultaco, Speen23, TDogg310, TexasAndroid, The Thing That ShouldNot Be, The X, Thegreateno, Tim bates, Toll booth, TonySt, Toytoy, Ttownfeen, Unmitigated Success, Unyoyega, Veganfood, Vsst, WriterHound, Xslim24x, Zelse81, Александър, 156anonymous edits

Arachidic acid  Source: http://en.wikipedia.org/w/index.php?oldid=502396836  Contributors: Albmont, Allen3, Arcadian, Aushulz, Beetstra, Black Orchid, Chem-awb, Clemwang,David.Throop, Dcirovic, Delta G, Denelson83, Diderot's dreams, DutchDevil, Edgar181, Jasonwithey, Jü, Keenan Pepper, Leyo, LilHelpa, LucioP, Mike hayes, Physchim62, Pro crast in a tor,Ronk01, ScAvenger lv, Shaddack, Stepa, Toytoy, 8 anonymous edits

Behenic acid  Source: http://en.wikipedia.org/w/index.php?oldid=518218954  Contributors: Albmont, Arcadian, Beetstra, Biscuittin, Chem-awb, Chris the speller, Cogiati, David.Throop,Dcirovic, Diderot's dreams, Edgar181, Elkman, Epop fr, Jay L09, Jü, Keenan Pepper, Parsival, ScAvenger lv, Seanwal111111, Shaddack, Space Cadet, Tomaxer, Torsolo, V8rik, Vuo, Waitak,WikHead, 9 ,علی ویکی anonymous edits

Lignoceric acid  Source: http://en.wikipedia.org/w/index.php?oldid=517837306  Contributors: Albmont, Balcer, Beetstra, Chem-awb, Christian75, Dcirovic, Diderot's dreams, Edgar181,Ghosts&empties, Hgrosser, Keenan Pepper, Kupirijo, Langbein Rise, M97uzivatel, Pdcook, Phil Ian Manning, Rifleman 82, ScAvenger lv, Shaddack, Yyy, 4 anonymous edits

Cerotic acid  Source: http://en.wikipedia.org/w/index.php?oldid=517941515  Contributors: Aballister, Albmont, Cburnett, ChemNerd, Dcirovic, Haligonian1, The chemistds, YOSF0113, ХоревСергей, 2 anonymous edits

Melissic acid  Source: http://en.wikipedia.org/w/index.php?oldid=510539430  Contributors: CMBJ, Cburnett, Joshuachandler11, Rjwilmsi, The chemistds, Yikrazuul, 2 anonymous edits

Image Sources, Licenses and Contributors 178

Image Sources, Licenses and ContributorsFile:Italian olive oil 2007.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Italian_olive_oil_2007.jpg  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors:my friendImage:Fat triglyceride shorthand formula.PNG  Source: http://en.wikipedia.org/w/index.php?title=File:Fat_triglyceride_shorthand_formula.PNG  License: Public Domain  Contributors:Wolfgang SchaeferImage:StatinPathway_WP430.png  Source: http://en.wikipedia.org/w/index.php?title=File:StatinPathway_WP430.png  License: Creative Commons Attribution 3.0  Contributors: NathanSalomonis, Alexander Pico, Kristina Hanspers, Thomas Kelder, Bruce ConklinFile:Magnify-clip.png  Source: http://en.wikipedia.org/w/index.php?title=File:Magnify-clip.png  License: Public Domain  Contributors: User:Erasoft24Image:Olive oil from Oneglia.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Olive_oil_from_Oneglia.jpg  License: Creative Commons Attribution-Share Alike  Contributors:LemoneFile:Olive oil.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Olive_oil.jpg  License: Creative Commons Attribution-Sharealike 2.0  Contributors: BAIAFile:Sunflowerseed oil.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Sunflowerseed_oil.jpg  License: GNU Free Documentation License  Contributors: Basilicofresco, Ygrek, 2anonymous editsFile:SpentcookingoilbinAustinTX.JPG  Source: http://en.wikipedia.org/w/index.php?title=File:SpentcookingoilbinAustinTX.JPG  License: Public Domain  Contributors: WhisperToMeFile:Trimyristin-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Trimyristin-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27File:Fatmouse.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Fatmouse.jpg  License: Public Domain  Contributors: Original uploader was Bigplankton at en.wikipedia Laterversions were uploaded by Sunholm at en.wikipedia.Image:Reuzel.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Reuzel.jpg  License: GNU Free Documentation License  Contributors: RasbakFile:Myristic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Myristic_acid.png  License: Public Domain  Contributors: Edgar181File:Myristic-acid-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Myristic-acid-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27Image:Fatchart.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Fatchart.svg  License: Creative Commons Attribution-ShareAlike 3.0 Unported  Contributors: Original uploader wasXyzzy n at en.wikipedia. Later version(s) were uploaded by Damnfuct at en.wikipedia.Image:Oleic-acid-skeletal.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Oleic-acid-skeletal.svg  License: Public Domain  Contributors: Benjah-bmm27, Edgar181, JyntoImage:Oleic-acid-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Oleic-acid-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27, JyntoImage:Linoleic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linoleic_acid.png  License: Public Domain  Contributors: Edgar181Image:Linoleic acid3D.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linoleic_acid3D.png  License: Public Domain  Contributors: Edgar181File:Crisco Cookbook 1912.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Crisco_Cookbook_1912.jpg  License: Public Domain  Contributors: Bohème, CopperKettle, GveretTered, Man vyiFile:Elaidic-acid-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Elaidic-acid-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27File:Oleic-acid-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Oleic-acid-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27, JyntoFile:Octadecanoic acid (stearic).png  Source: http://en.wikipedia.org/w/index.php?title=File:Octadecanoic_acid_(stearic).png  License: Creative Commons Attribution-Share Alike Contributors: BorgdylanFile:Elaidic-acid-2D-skeletal.png  Source: http://en.wikipedia.org/w/index.php?title=File:Elaidic-acid-2D-skeletal.png  License: Public Domain  Contributors: Benjah-bmm27File:Oleic-acid-skeletal.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Oleic-acid-skeletal.svg  License: Public Domain  Contributors: Benjah-bmm27, Edgar181, JyntoFile:Stearic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Stearic_acid.svg  License: Public Domain  Contributors: Benjah-bmm27, Edgar181, Slashme, TimVickersFile:Wilhelm Normann.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Wilhelm_Normann.jpg  License: Public Domain  Contributors: CmhFile:SalersBreed Cow 5.JPG  Source: http://en.wikipedia.org/w/index.php?title=File:SalersBreed_Cow_5.JPG  License: GNU Free Documentation License  Contributors: B.navez, Dbenbenn,Fabien1309, Kersti Nebelsiek, RmhermenImage:LAnumbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:LAnumbering.png  License: Public Domain  Contributors: Original uploader was Edgar181 at en.wikipediaImage:Oenothera biennis 20050825 962.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Oenothera_biennis_20050825_962.jpg  License: Creative Commons Attribution-Sharealike2.5  Contributors: User:Georg SlickersImage:ALAnumbering.svg  Source: http://en.wikipedia.org/w/index.php?title=File:ALAnumbering.svg  License: Public domain  Contributors: en:User:Edgar181Image:EPAnumbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:EPAnumbering.png  License: Public Domain  Contributors: Edgar181Image:DHAnumbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:DHAnumbering.png  License: Public Domain  Contributors: Edgar181Image:Flax seeds.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Flax_seeds.jpg  License: Creative Commons Attribution-Sharealike 2.5  Contributors: Denis Barthel, Foroa, Ies,Joanjoc, Kri, Rumun999, Schwäbin, WayneRayFile:Butyric acid acsv.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Butyric_acid_acsv.svg  License: Public Domain  Contributors: Calvero.Image:rasyslami.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Rasyslami.jpg  License: GNU Free Documentation License  Contributors: Original uploader was (Automatedconversion) at en.wikipediaImage:Isomers of oleic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Isomers_of_oleic_acid.png  License: Public Domain  Contributors: Edgar181File:Fatty acid numbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:Fatty_acid_numbering.png  License: Public Domain  Contributors: user:FoobarImage:Fatty acid numbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:Fatty_acid_numbering.png  License: Public Domain  Contributors: user:FoobarImage:Interesterification rxn.png  Source: http://en.wikipedia.org/w/index.php?title=File:Interesterification_rxn.png  License: Public Domain  Contributors: RoadnottakenFile:Acetic-acid-2D-skeletal.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Acetic-acid-2D-skeletal.svg  License: Public Domain  Contributors: Benjah-bmm27, Bryan Derksen,Calvero, Dryke, Interiot, SamuliliFile:Caproic acid acsv.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Caproic_acid_acsv.svg  License: Public Domain  Contributors: Calvero.Image:Palmitoleic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Palmitoleic_acid.svg  License: Public Domain  Contributors: Mrgreen71File:Yes check.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg  License: Public Domain  Contributors: AnomieFile:X mark.svg  Source: http://en.wikipedia.org/w/index.php?title=File:X_mark.svg  License: Public Domain  Contributors: User:GmaxwellImage:Myristoleic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Myristoleic_acid.png  License: Public Domain  Contributors: Edgar181Image:Oleic-acid-based-on-xtal-1997-2D-skeletal.png  Source: http://en.wikipedia.org/w/index.php?title=File:Oleic-acid-based-on-xtal-1997-2D-skeletal.png  License: Public Domain Contributors: Ben MillsImage:Sapienic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Sapienic_acid.svg  License: Public Domain  Contributors: YikrazuulImage:Elaidic-acid-2D-skeletal-reverse.png  Source: http://en.wikipedia.org/w/index.php?title=File:Elaidic-acid-2D-skeletal-reverse.png  License: Public Domain  Contributors: Ben MillsImage:Elaidic-acid-from-xtal-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Elaidic-acid-from-xtal-3D-balls.png  License: Public Domain  Contributors: Ben MillsImage:Elaidic-acid-from-xtal-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Elaidic-acid-from-xtal-3D-vdW.png  License: Public Domain  Contributors: Ben MillsImage:Trans-vaccenic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Trans-vaccenic_acid.svg  License: Public Domain  Contributors: Fvasconcellos, JyntoImage:Vaccenic-acid-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Vaccenic-acid-3D-balls.png  License: Public Domain  Contributors: Jynto and Ben MillsImage:Linoelaidic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linoelaidic_acid.png  License: Public Domain  Contributors: Edgar181Image:Linoleic-acid-from-xtal-1979-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linoleic-acid-from-xtal-1979-3D-balls.png  License: Public Domain  Contributors:Ben MillsImage:Linoleic-acid-from-xtal-1979-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linoleic-acid-from-xtal-1979-3D-vdW.png  License: Public Domain  Contributors:Ben Mills

Image Sources, Licenses and Contributors 179

File:Linoleic Acid Metabolism.gif  Source: http://en.wikipedia.org/w/index.php?title=File:Linoleic_Acid_Metabolism.gif  License: Public Domain  Contributors: Logan RutherfordImage:Arachidonic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Arachidonic_acid.svg  License: Creative Commons Attribution-Share Alike  Contributors: Edward theConfessorFile:Arachidonic acid spacefill.png  Source: http://en.wikipedia.org/w/index.php?title=File:Arachidonic_acid_spacefill.png  License: Public Domain  Contributors: SubDural12File:Arachidonic acid2.png  Source: http://en.wikipedia.org/w/index.php?title=File:Arachidonic_acid2.png  License: Public Domain  Contributors: SubDural12File:AAnumbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:AAnumbering.png  License: Public Domain  Contributors: User:Edgar181Image:Steaks.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Steaks.jpg  License: Public Domain  Contributors: Jon SullivanImage:Eicosanoid synthesis.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Eicosanoid_synthesis.svg  License: GNU Free Documentation License  Contributors: Jfdwolff,whitespace removed byImage:ALAnumbering.png  Source: http://en.wikipedia.org/w/index.php?title=File:ALAnumbering.png  License: Public domain  Contributors: en:User:Edgar181Image:Linolenic-acid-3D-vdW.png  Source: http://en.wikipedia.org/w/index.php?title=File:Linolenic-acid-3D-vdW.png  License: Public Domain  Contributors: Benjah-bmm27, JyntoImage:Beklädnadsväxter, Linum usitatissimum, Nordisk familjebok.png  Source:http://en.wikipedia.org/w/index.php?title=File:Beklädnadsväxter,_Linum_usitatissimum,_Nordisk_familjebok.png  License: Public Domain  Contributors: Guérin Nicolas, Lokal Profil, 1anonymous editsFile:Eicosapentaenoic acid spacefill.png  Source: http://en.wikipedia.org/w/index.php?title=File:Eicosapentaenoic_acid_spacefill.png  License: Public Domain  Contributors: SubDural12File:Eicosapentaenoic acid2.png  Source: http://en.wikipedia.org/w/index.php?title=File:Eicosapentaenoic_acid2.png  License: Public Domain  Contributors: SubDural12Image:Röding, Iduns kokbok.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Röding,_Iduns_kokbok.jpg  License: Public Domain  Contributors: CambridgeBayWeather,Courcelles, Haplochromis, Liftarn, Liné1, Neil916, Quibik, VäskImage:Erucic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Erucic_acid.png  License: Public domain  Contributors: User:Edgar181Image:RanscombeFarmRape9919.JPG  Source: http://en.wikipedia.org/w/index.php?title=File:RanscombeFarmRape9919.JPG  License: Creative Commons Attribution-ShareAlike 3.0Unported  Contributors: ClemRutterImage:DHA_numbers.svg  Source: http://en.wikipedia.org/w/index.php?title=File:DHA_numbers.svg  License: Public Domain  Contributors: Timlev37 (talk)Image:Caprylic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Caprylic_acid.svg  License: Public Domain  Contributors: Calvero.Image:Caprylic-acid-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Caprylic-acid-3D-balls.png  License: Public Domain  Contributors: Jynto and Ben MillsImage:Decanoic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Decanoic_acid.png  License: Public Domain  Contributors: Original uploader was Edgar181 at en.wikipediaImage:Decanoic-acid-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Decanoic-acid-3D-balls.png  License: Public Domain  Contributors: Jynto and Ben MillsImage:Lauric acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Lauric_acid.png  License: Public Domain  Contributors: Original uploader was Edgar181 at en.wikipediaImage:Lauric-acid-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Lauric-acid-3D-balls.png  License: Public Domain  Contributors: Ben MillsImage:myristic acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Myristic_acid.png  License: Public Domain  Contributors: Edgar181Image:Palmitic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Palmitic_acid.svg  License: Creative Commons Attribution-Sharealike 3.0,2.5,2.0,1.0  Contributors: Mrgreen71Image:Palmitic-acid-3D-balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Palmitic-acid-3D-balls.png  License: Public Domain  Contributors: Jynto and Ben MillsImage:Stearic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Stearic_acid.svg  License: Public Domain  Contributors: Benjah-bmm27, Edgar181, Slashme, TimVickersImage:Stearic-acid-3D-Balls.png  Source: http://en.wikipedia.org/w/index.php?title=File:Stearic-acid-3D-Balls.png  License: Creative Commons Zero  Contributors: Matt18224Image:Arachinsäure.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Arachinsäure.svg  License: Public Domain  Contributors: NEUROtikerImage:Arachidic Acid.png  Source: http://en.wikipedia.org/w/index.php?title=File:Arachidic_Acid.png  License: Creative Commons Attribution-Sharealike 3.0  Contributors: Ronk01Image:Behenic Acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Behenic_Acid.svg  License: Public Domain  Contributors: ZooFariImage:Moringa oleifera Blanco1.125.png  Source: http://en.wikipedia.org/w/index.php?title=File:Moringa_oleifera_Blanco1.125.png  License: Public Domain  Contributors: Francisco ManuelBlanco (O.S.A.)Image:Lignocerīnskābe.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Lignocerīnskābe.svg  License: Public Domain  Contributors: YyyImage:Cerotic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Cerotic_acid.svg  License: Public Domain  Contributors: User:Хорев СергейImage:Melissic acid.svg  Source: http://en.wikipedia.org/w/index.php?title=File:Melissic_acid.svg  License: Public Domain  Contributors: Yikrazuul

License 180

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