Primary Metabolism

Organic acids & juicesMalic acid: (apple juice) active ingredient in many sour/tart foods; salts & esters are malates. first isolated from apple juice by Carl Wilh. Scheele 1785.

Tartaric acid (grape juice), white cryst org acid occ in many plants: grapes, banana & tamarinds, main acid in wine. sour taste, antioxidant. tartrates

Benzoic acid (cranberry juice) benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. Strong preservative & antifungal compound. Urinary tract disinfections common preservative in many foods, cons. Safe.

Citric acid ( lemon juice): natural preservative, benign cleaning agent & antioxidant. adds sour taste to foods (spice) Important intermediate of citric acid cycle that occurs in almost all life. Lemons, limes have particularly high concentrations: 8% dry weight (6g per 100g juice)

Malic acidMalic acid causes the sourness of green apples and grapes conferrring a tart taste to wine. From malus = apple

1 M kg malic acid produced / year. Food additive E 296 as source of tartness in “extreme candy” like Sour Punch.

Malic acid is a natural chelator provided as Mg malate and will detoxify the gut from heavy metal deposits.

SournessSourness is due to presence of free H + ions released by acids.

Acetic acid in vinegar

Oxalic acid in Rhubarb, Rumex dock & spinach

Phosphoric acid in coke

Citric acid in lemonade

Carbonic acid in sodasSour receptor protein has – COOH groups with dissociation being affected by H+ ion concentration

Sour taste means low pH and little danger of bacterial contamination as in sour milk, cheese, beer, wine, silage

Acetic acid & AcetaldehydeAcetic acid is is a colourless liquid & the main component of vinegar, it has a distinctive sour taste and pungent smell. Although it is classified as a weak acid, acetic acid is highly dangerous to skin.

Vinegar was known early in history as the natural result of wine being exposed to air & the omnipresent acetobacter. In the 8th century, Jabir Ibn Hayyan (Geber) was the first to concentrate acetic acid from vinegar through distillation. Table vinegar is typically 4 - 8% acetic acid by mass. Vinegar is used as a condiment, and in the pickling of vegetables.

Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, It is also produced by oxidation of ethanol and is popularly believed to be a cause of hangovers. The drug disulfiram (Antabuse) prevents the oxidation of acetaldehyde to acetic acid, and produces a hangover. & is used as a deterrent for alcoholics.

Sumac - the vinegar or lemonade treeThe drupes of the genus Rhus are ground into a deep-red powder used as a spice in Middle Eastern cuisine to add a lemony taste to salads or meat (turkish cuisine) In North America, the smooth sumac (Rhus glabra), and the staghorn sumac (Rhus typhina), are sometimes used to make a beverage, termed "sumac-ade" or "Indian lemonade" or "rhus juice". This drink is made by soaking the drupes in cold water, rubbing them to extract the essence, straining the liquid through a cotton cloth and sweetening it. Native Americans also used the leaves and berries of the smooth and staghorn sumacs combined with tobacco in traditional smoking mixtures.

The leaves of certain sumacs yield tannin (mostly pyrogallol), a substance used in vegetable tanning. Leather tanned with sumac is flexible, light in weight, and light in color, even bordering on being white. Also many organic acids

Dried sumac wood is fluorescent under long-wave UV light

Constituents of the vinegar tree: tannins, anthocyanins, organic acids: malic, citric, & tataric plus smaller amounts of succinic, maleic, fumaric and ascorbic acid

Rhus typha, staghorn sumach

Skun cabbage family Geranium spp.

The Araceae are well-known for having sharp crystals of

BenzaldehydeThis colorless liquid has a characteristic pleasant almond-like odor & is the primary component of bitter almond oil. It is commonly employed to confer almond flavor.

Almonds, apricots, apples and cherry kernels, contain significant amounts of amygdalin.

This glycoside breaks up under enzyme catalysis into benzaldehyde, hydrocyanic acid and two molecules of glucose

Benzyl Acetate – the smell of JasmineThis colorless liquid has a characteristic pleasant almond-like odor & is the primary component of bitter almond oil. It is commonly employed to confer almond flavor.

Benzyl acetate is the ester formed by condensation of benzyl alcohol and acetic acid.

Benzyl acetate is found naturally in many flowers. has pleasant sweet aroma reminiscent of jasmine.

It is the primary constituent of the essential oils from the flowers jasmine, ylang-ylang and tobira. It. Consequently, it is used widely in perfumery and cosmetics for its aroma and in flavorings to impart apple and pear flavors.

Benzoic acid in fruits + foods

Benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic solvents makes this experiment especially safe.

Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Amounts found in most berries are around 0.05%. Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis idaea; bilberry, V. macrocarpon) contain as 300-1300 mg free benzoic acid per kg fruit 0.1 % FW.

Use for benzoic acid as a preservative in food requires between 0.05 – 0.1%. Concern has been expressed that benzoic acid may react with ascorbic acid (vitamin C) in some soft drinks, forming some carcinogenic benzene.

Food preservation1762 Italian priest L. Spallanzani : discovered that meat did not spoil when heated in sealed flask. 1795 Nicholas Appert started to can foods in glass jars for Napoleons army 1810 English Peter Durand started tin cans. 1860 Isaac Solomon of Baltimore adding CaCl2 raised boiling temp & shortened processing time from 6 h to 45 min

canned foods are full with NaCl & sugar

“No preservatives added” any chemical that retards deterirotion unless salt, sugar, spices, wood smoke, insecticides & herbicides sorbic acid, benzoic acid, sulfur dioxide, propionate & nitrites

Poppers are bottles filled with liquid alkyl nitrites like amyl, butyl &isobutyl nitrite dilate the blood vessels and allow more blood to get to the heart. They're sniffed straight from the bottle and deliver a short, sharp high. Poppers are sold in sex shops, clubs and gay bars. Street names: Ram, Thrust,Kix

Benzoic acid in perfumesBenzoin resin = styrax resin = benzoin is obtained from the bark of trees in the genus Styrax. Benzoin Sumatra is obtained from Styrax benzoin grown on the island of Sumatra. Both varieties are pathogenic resins, which are exuded from the tree when it is damaged. Its principle component is benzoic acid.

In perfumery, benzoin is used as a fixative, slowing the dispersion of essential oils & other fragrances into the air. It is also used in medicine. Tincture of benzoin has two main medical uses: aseptic treatment for blisters damaged skin, and as an inhalant in case of bronchitis & asthma.

Benzoin resin is important aroma in incenses: major comp. of incense of Russian Orthodox Christians

also in Japanese incense, Indian incense, Chinese incense, and Papier d'Arménie. Sambrani is a popular Indian incense used to scent hair and prevent infections.

Leukoptape + TOB treats blisters on trips

Lab exercise: isolation of citrate citric acid is a natural preservative & is concentrated in lemons & limes having up to 8% of the dry weight powder crystallizes from hot water , monohydrate from cold water Isolation from lemon juice: 1. measure 90 ml of thawed “frozen lemon juice”concentrate into a 250 ml beaker and carefully add 10 % NaOH solution until you have reached a slightly alkaline pH. Thank Gosh, you do not need a pH indicator since at this point the juice turns from a clear yellow into a brownish color.2. Strain solution through sieve to remove larger pulp particles & . seeds (you keep for better days) & than through filter paper 3. place filtrate into a 200-ml beaker and add 5 ml of CaCl2 solutio . for each 10 ml filtrate while constantly stirring. 4. Heat to boiling & filter off the copious mount of Ca hydro citrate 5. Resuspend in minimum of cold water, heat to boiling & collectthe insoluble Ca Citrate by filtration. Allow salt to air dry.

6. Dissolve Ca citrate in 10 % sulphuric acid toprecipitate CaSO4

Organic acids stop aging … for a whileΑ- Hydroxy acids (AHAs) the first over-the-counter anti-aging preparations that work. Act as exfoliants = removing old skin & encourage new growth, fading discoloration (liver spots = lentigenes) & wrinkle, minimum concentration that works is 10 % acid. Results appear after many months of daily use.- Patience

Lactic acid, is hygroscopic substance & natural preservative found in sour milk, yogurt, cottage cheese & wheat beers glycolic acid is isolated form sugar cane, canteloupe citric acid is a natural preservative & is concentrated in lemons & limes having up to 8% of the dry weight powder crystallizes from hot water ,

Facial peels: Increase acid concentration to 30 to 70 % (plastic surgeon) light chemical peel (you are temporily ugly after that!)

Deeper peels: use higher conc. of phenol or tri-chlore-acetic acid (TCA) causes crust-like scabs appear after the application - takes tow weeks to heal – but for beauty ……..

Lactic acid

Citric acid

Natural Cosmetics with everyday products

Plant saps & extracts do have various pH values, due to storage of different amounts and species of organic acids inside the vacuole. All plant cells have a pH between 6.8 and 7.3 inside of the cytoplasm. Lemons have a pH of 2.0, cucumber of pH 7.0. The stems of cucumber and pumpkins may even show a pH that is clearly alkaline or above 7 (establishProduct

Approximate pH

Abalone

6.1 - 6.5

Aloe Vera

6.1

Apples

3.3 - 3.9

Apricots

pH of several plants & plant productsPLANT pH PLANT pH

Aloe Vera 6.1 Apples 3.3 - 3.9 Asparagus 6. Bananas 4.5 - 5.2 Avocados 6.3 - 6.6 Grapefruit 4.8 – 5.3Beers 4.0 - 5.0 Apricots 3.3 - 4.8Beets 5.3 - 6.6 Blackberries 3.9 - 4.5Cabbage 5.2 - 5.4 Blueberries 3.1 - 3.4 Carrots 5.9 - 6.3 Cherries 3.2 - 4.5Coconut 5.5 - 7.8 Cranberry juice 2.3 - 2.5Celery 5.7 - 6.0 Chili sauce 2.8 - 3.7Horseradish 5.4 Grapes 3.5 - 4.5Mangos 5.8 - 6.0 Limes 1.8 - 2.0Olives, black 6.0 - 7.0 fermented green Olives 3.6 - 3.6Peas 5.8 - 6.4 Plums 2.8 - 3.0Potatoes 5.6 - 6.0 Sauerkraut 3.4 - 3.6Pumpkin 4.8 - 5.2 Raspberries 3.2 - 3.6Spinach 5.5 - 6.8 Rhubarb 3.1 - 3.2Squash 5.0 - 5.4 Strawberries 3.0 - 3.9Tea 7.2 Tomatoes 4.3 - 4.9

proteinogenic amino acids Amino acids serve as the monomers of proteins.

22 amino acids are naturally incorporated into polypeptides and are called proteinogenic amino acids.

8 proteinogenic amino acids are called"essential" for humans because they cannot be created from other compounds by the human body, and so must be taken in as food.

Essential amino acids

In addition, the amino acids arginine, cysteine, glycine, glutamine and tyrosine are considered conditionally essential, meaning they must be supplied exogenously to specific populations that do not synthesize them

They are called essential not because they are more important to life than the others, but because the body does not synthesize them, making it essential to include them in one's diet .

Nine amino acids are essential for humans: phenylalanine, valine, threonine, tryptophan, isoleucine, methionine, histidine, leucine, and lysine. Arginine is required by infants and growing kids, it is an important supplement in producing nitric oxide.

Animal sources such as meat,, eggs, fish, milk, cheese provide all of the essential amino acids. Complete proteins are only found in some plant sourcessuch as spirulina, quinoa, soy, buckwheat, hempseed, amaranth..

Other essential acids

By convention, the term vitamin does refers essential organic substances that are needed in small quantity and does not include other essentials such as minerals, essential fatty acids, or essential amino acids needed in larger amounts . Thirteen vitamins are universally recognized at present. Ascorbic acid (vitamin C) is a vitamin for humans, but not for other animals,

Essential substances are such that humans & other animals must ingest because their body requires them for functioning although they cannot synthesize them on their own.

Nine amino acids are essential for humans: phenylalanine, valine, threonine, tryptophan, isoleucine, methionine, histidine, leucine, and lysine. arginine

Essential fatty acids, or EFAs, are those fatty acids that are required for biological processes, and not those that only act as fuel. Two EFAs are known for humans: alpha-linolenic acid (an omega-3 fatty acid) & linoleic acid (an omega-6 fatty acid. When the two EFAs were first discovered in 1923, they were designated Vitamin F. In 1930, work showed that the two EFAs are better classified as fats than vitamins

Essential Fatty Acids: you need to supplement omega-6 fatty acids: ω-6 important for skin & eye functions

linoleic acid converted to gamma-linolenic acid (GLA) in safflower, sunflower & corn oils, flaxseed, borage oil brain

Arachidonic acid – unsat. 20-C chain found in peanut oil (Arachis hypogaea) arachidonic acid cascade leads to pro-inflammatory agents called prostaglandins(1963) –members of the larger group of eicosanoids

Omega-3 fatty acids eicosanoids from ω-3 FA are anti-inflammat

18:3 α–linolenic acid ALA: in flax oil

20:5 eicopentaenoic acid (EPA) in fish oil

22:6 docosahexanenoic acid (DHA) in fish oil

Essential for the normal growth of young children & animals first called Vitamin F when discovered in 1923

Balanced diet of essentail AAs

The tree sister method of agriculture provides a balanced diet that corn alone cannot provide. The image here, is from a Navajo healing sandpainting, and each plant corresponds here to a compass direction as well.

Semah, or tobacco, is one of the four sacred plants. It represents the Eastern Direction and the mind. Sopme use a form of tobacco known as kinikinik,

The four sacred plants of the American SW were aligned with the four winds

The squash is the western direction. It provides water and vessels.Corn , is one of the most sacred four plants. It represents the Northern Direction and is the staple food crop,

The squash are the souther Direction and they grow in perfect harmony with corn winding around the stem

Non-proteinogenic amino acidsAcetyl-L-Carnitine (ALC or ALCAR) has been found to stimulate capillary blood flow & so to improve brain performance & cognitive functions, slows Alzheimer's disease 500 mg/day ALCAR

Theanine: in high conc. in tea leaves & some fungi -neuroprotective

Carnitine is produced from the AA lysine or methionine, natural sources are red meat, cottage cheese, nuts & seeds: pumpkin, sunflower, sesame, beans, peas, peanuts. C. is required to process fats f

Cystathione: many plant species & also human urine

Stizolobic acid: occurs in plants & toadstools (toxic mushrooms) possible ijteraction with excitatory synaptic AA receptors

Nicotianine : from tobacco leaves & Shiitake mushrooms

Acetyl L Carnitine

Toxic non-proteinogenic amino acids

Canavanine is a non-proteinogenic α-amino acid found in in the seeds of certain leguminous plants like jack bean and the perennial crop alfalfa or lucerne Medicago sativa. It is structurally related to the proteinogenic α-amino acid L-arginine. It serves both as a highly deleterious defensive compound against herbivores and a vital storage of nitrogen for the growing embryo. This plant exhibits autotoxicity, it is difficult for alfalfa seed to grow in existing stands of alfalfa fields must be rotated.

Canavalia is a genus of vines endemic to the Hawaiian Islands & commonly known as jack-beans. The Common Jack-bean is also known as the plant from which the lectin concanavalin A, con A is produced.

The mechanism of canavanine's toxicity is that organisms that consume it typically mistakenly incorporate it into their own proteins in place of L-arginine, thereby producing structurally aberrant proteins that may not function properly.

Jack beans

alfalfa

non-proteinogenic amino acids as neurotransmitters

Canavanine is a leguminous plants like jack bean and the perennial crop alfalfa or lucerne Medicago sativa. It is structurally related to the proteinogenic α-amino acid L-arginine. It serves both as a highly GABA gradient from stigma to ovule helps guiding the pollen tube to fertilization.

GABA or γ-Aminobutyric acid is not ever incorporated into a protein. It is the chief inhibitory neurotransmitter in the mammalian central nervous system. It controls neuronal excitability. In humans, GABA is also directly responsible for the regulation of muscle tone.

GHB or γ-hydroxybutyric acid is a byproduct of the GABa catabolism. Illegal since 1991, it induces a trance that mimics sleep. When mixed into alcohol it is used as a DRD or date-rape-drug by inducing trance + slowed heart rate & hypothermia. The three most common DRDs are alcohol and two sleep aids; gamma-hydroxybutyric acid, and benzodiazepines: Rohypnol (flunitrazepam,)

non-proteinogenic amino acids as neurotransmitters

L-DOPA is dietary supplement and prescription –levopoda- for Parkinson disease ovule helps guiding the pollen tube to fertilization.

L-DOPA (L-3,4-dihydroxyphenylalanine) is an AA that is made from the amino acid L-tyrosine. L-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) catecholamines.. L-DOPA crosses the protective blood-brain barrier, whereas dopamine itself cannot

Vicia faba or fava beans contain non-proteinogenic AA L-DOPA or levopoda in high amounts 500 mg in one cup of beans same amount in 2 pills. Another good source is Mucuna pruriens (Velvet Bean)

Caution: Fava beans also contain Tyramine, which when taken together with MAO inhibitors increase blood pressure in so-called “cheese response”.

non-proteinogenic amino acids as itchy aphrodisiacs

Traditionally, M. pruriens has been used as an effective aphrodisiac. It is still used to increase libido in both men and women due to its dopamine inducing properties. Dopamine has a profound influence on sexual function.

The plant and its extracts have been long used in tribal communities as a toxin antagonist for various snakebites. M.pruriens seeds have also been found to have antidepressant properties and formulations of the seed powder have shown promise in the management and treatment of Parkinson disease

Mucuna pruriens is a tropical legume known as velvet bean or cowitch found in Africa, India and the Caribbean. The plant is infamous for its extreme itchiness produced on contact, particularly with the young foliage and the seed pods. The hairs lining the seed pods contain 5-hydroxytryptamine (serotonin) which cause the severe itching.

non-proteinogenic amino acids as neurotoxins

Lathyrism or Neurolathyrism is a neurological disease of humans animals, caused by eating legumes of the genus Lathyrus. This problem is mainly with Lathyrus sativus (also known as Grass pea,) and to a lesser degree with L. cicera, L ochrus and L clymenum containing the toxin ODAP, also β-N-oxalyl-amino-L-alanine or BOAA)

The neurotoxic non-proteinogenic AA ODAP acts as a non-metabolized structural analogue of the neurotransmitter glutamate. Ingestion of toxin results mostly from ignorance and despair of malnutrition (politically correct expression for hunger).

The related β-methyl-amino-alanine (BMAA) is found in cycad seeds found in Guam, where the native Chamorro detoxify the seeds of Cycas micronesia by washing them for weeks. However, they eat bats that accumulate large amounts of the BMAA. Do not eat too many bats!

proteinogenic amino acids as flavors; MSGMonosodium glutamate, also known as sodium glutamate and MSG, is a naturally occurring non-essential amino acid. It is used as a food additive and is commonly marketed as a flavour enhancer. It has the HS code 29224220 and the E number E621

Modern commercial MSG is produced by fermentation] of starch, sugar beets, sugar cane or molasses. About 1.5 million tons were sold in 2001. MSG is used commercially as a flavor enhancer. Although once associated with foods in Chinese restaurants, MSG is now used in many processed foods.

MSG use is controversial although considered safe by the FDA

a taste of meat, lecture for herbivores (vegetarians) The taste of oyster mushrooms is mediated by the amino acid MSG = monosodium glutamate in its tissue. This in itself – however – is only a taste enhancer. Plerotus ostreatushas a slightly meaty taste which is caused by proteins that contain a high share of glutamate.

MSG is a HUGE player with people suffering needlessly from multiple sclerosis MG and other "diseases.“

Being an excitotoxin, it destroys the myelin sheath and kills brain cells. Avoiding MSGwill probably eliminate most, if not all MSsymptoms.

Traditional Asian cuisine had used seaweed, which contains high concentrations of glutamic acid, it was not until 1907 that MSG was isolated by Kikunae Ikeda.

Essential Fatty Acids: you need to supplement omega-6 fatty acids: ω-6 important for skin & eye functions

linoleic acid converted to gamma-linolenic acid (GLA) in safflower, sunflower & corn oils, flaxseed, borage oil brain

Arachidonic acid – unsat. 20-C chain found in peanut oil (Arachis hypogaea) arachidonic acid cascade leads to pro-inflammatory agents called prostaglandins(1963) –members of the larger group of eicosanoids

Omega-3 fatty acids eicosanoids from ω-3 FA are anti-inflammat

18:3 α–linolenic acid ALA: in flax oil

20:5 eicopentaenoic acid (EPA) in fish oil

22:6 docosahexanenoic acid (DHA) in fish oil

Essential for the normal growth of young children & animals first called Vitamin F when discovered in 1923

What is so special about Chia seeds?Salvia hispanica, commonly known as chia in the mint family, Lamiaceae, is native to central and southern Mexico and Guatemala. The 16th century Codex Mendoza provides evidence that it was cultivated by the Aztec in pre-Columbian times as an important crop plant .[2]

The soaked seeds are gelatinous in texture and are used in gruels, porridges and puddings. Chia seeds placed in water or fruit juice are consumed in Mexico and known as chia fresca. Chia sprouts on porous clay figurines icon of Chia Pet.

Chia is grown commercially for its seed, a food that is rich in omega-3 fatty acids, since the seeds yield 25–30% extractable oil, including α-linolenic acid (ALA). Chia seeds are small ovals with a diameter of about 1 mm . They are mottled with brown, gray, black and white.

Some active oils Olive oil is made from macerated fruits from which bitter phenoles need to be removed. The pulp of the processed fruit is pressed.

Castor oil is pressed from seeds which contain highly toxic agglutinating protein ricin and mildly toxic alkaloid ricine plus dangerous allergen CB-A. Laxative action is causedby ricinoleic acid. Mostly used for soaps, paints, Turkey red oil and in hydrogenated form used for rocket and aircraft engines. When seeds are pressed cold – ie at temps below 50 C which supp. excludes ricin from getting out.

Rapeseed oil is obtained from Brassica napus seeds. Contain erucic acid ( a good lubricating oil) & withstands very high temperatures (steel production).

Peanut oil obtained from Arachis hypogaea contains arachidonic acid which support inflammatory responses . Refers a pleasant taste to fried food and does not smoke during high temperatures.

Vegetable Oils & Waxes Olive oil were used since 5 000 years. One tree still grows in the Sahara. Highly appreciated in the Mediterreanean.

Vegetable oils derive from seeds (coconut, castor beans,peanuts, soybens, cotton, flax, walnut) or fruits (avocado, olive, palm fruits).

Vege oils contain omega-3 fatty acids which are essential fatty acids. Most vege oils are unsaturated; except for palm & coconut oil

Coconut oil is a fat since it is hard at room temps. It is obtained by pressing the dried meat of the nut. Hydrogenized it became an important fat for baking and also for margarine. How do you hydrogenate a plant oil so that it will turn solid at RT? 1896 French chemists found that unsaturated organic compounds mix with hydrogen gas in their vapor state in the presence of catalytic Nickel powder. A mixture of Nickel powder + oil is heated while hydrogen gas bubbles through it. The hardeend oil settles to the bottom outlet.

Plants that produce oils

Castor bean 20-50 lbs Cloves 15-20 lbs Nutmeg 10 lbs Mace 9 lbs Caraway seed 4 lbs Aniseed 3 lbs Lavender 2 lbs Patchouli 1 lbs Sandalwood 1 lbs

These values give you an idea of whether it is worthwhile to press or distill the plants for their oil. Note that most lab exercises call for the distillation of cloves. Why?

Warning: Do not cold-press or distil Castor beans since it contains deadly blood-agglutinating proteins plus a fatty acid that acts as a potent laxative!!!!

The list of plants producing fatty oils or essential oils is indeed a long one. Here we give some examples for the oil yields of 100 pounds of ...

Peppermint 15 oz Calamus root 14 oz Cedarwood 13 oz Majoram 12 oz = 1 lbs Cassia 12 oz Orange peel 10 oz Hops 1 oz Rose petals 0.2 oz Violet 0.1 oz

Ketone bodies from Cocos oil prevent AlzheimerFirst, the brain makes its own insulin. When your brain's production of insulin decreases, it begins to starve, as it's deprived of the glucose-converted energy it needs to function normally. This is what happens to Alzheimer's patients -- portions of their brain start to atrophy, or starve, leading eventual loss of memory, speech, movement and personality.

primary source of ketone bodies are the medium chain triglycerides (MCT) as found in coconut oil 66 % MCTs. This may even restore and renew neuron and nerve function after damage has set in. MCTs go directly to your liver, which naturally converts the oil into ketones, bypassing the bile (routing of long chain triglycerides (LCTs). Your liver then immediately releases the ketones into the bloodstream go to the brain to be used as alternative fuel.

Myrmecochory or manipulating the ant brain

Ant propagated seeds are characterized by seeds with appendages in the form of fatbodies = elaiosomes. These are found in clelandine Chelidonium, the lablab beans, in larkspur Corydalis, in Ranunculus ficaria, Viola odorata, the Lamium maculatum, Melampyrum bloodroot, woods poppy , Trillium, Erythronium, Castor bean, Datura, Dicentra and tropical plants.

The distribution of plant seeds through ants is one of the amazing examples of co-evolution & intelligent behavior of plants.

Tasks: 1. Take a closer look (microscope) at the seeds provided today.

2. you should do this one on your own. Visit an anthill & drop pH paper on it &also some seeds having elaiosomes. You will have 30 min of entertainment.

volatile communication Stick insects throw brown, shiny hard-shelled eggs with

an detachable appendage rich in lipids – they mimic seeds

ants transport them to the safety of their nest, severe the appendage and dump them now far away from home.

Many plants are as sedentary as the stick and need the same help in propagating their species.

Bloodroot (Sanguinaria canadensis), castor bean (Ricinus officinalis) and many other seeds have oilbodies that attract ants that store them safely in their nests undergound, severe the elaiosome and let them germinate on their well fertilized garbage dump.

Cape of South Africa invaded by foreign ants and many plants disappeared1.signal is oleic acid which also signifies a dead ant impulse to get it to exit. oleic

acid is one of the principal unsaturarted fatty acids of plants:

2. signal is 1,2- diolein, insect fat smelling like ant brood

Policosanol (or polycosanol)Policosanol (or polycosanol) is generic term for an extract of plant waxes that consists of a mixture of a few fatty alcohols derived from the waxes of such plants as sugar cane, yams, beeswax. Most prevalent alcohol in policosanol is octacosanol, followed by triacontanol.Used as supplement to lower (bad) LDL cholesterol and increase (good) HDL cholesterol and so to prevent artherosclerosis, Rayleigh’s disease, coronary and stroke.

Policosanol (PPG) is produced, promoted & studied extensively in Cuba, where pharmaceutical research & sugar cane both exist in abundance.

Acrolein – the smell of barbecued ( burnt) meat Acrolein: is an colorless, volatile aldehyde that is formed from heated fats as a derivative of glycerol. It has a piercing, disagreeable, acrid smell similar to that of burning fat. It contributes to the smell of barbecue and the taste of caramelized sugar. It combines with wood smoke = formaldehyde, which attacks the eyes to tears at campfires.

It is a severe pulmonary irritant & lachrymatory agent. Skin exposure to acrolein causes serious damage. Studies on rats showed an increase in cancerous tumors from ingestion, but not from inhalation.

Acrolein test is a test for the presence of glycerin or fats. When a fat is heated in the presence of a dehydrating agent such as KHSO4, the glycerol portion of the molecule is dehydrated to form the unsaturated aldehyde, acrolein (CH2=CH-CHO), which smells like burnt grease. Alternatively, sample is heated with potassium bisulfate, and acrolein is released if the test is positive When glycerol is heated to 280 °C, it decomposes into acrolein.

Linseed oil – “usitatissimum ‘ pardon my Latin

also known as flaxseed oil, is a clear to yellowish oil obtained from the dried ripe seeds of the flax plant (Linum usitatissimum) by cold pressing. Due to its high levels of α-Linolenic acid (an essential Omega-3 fatty acid), it is used as a nutritional supplement.

Technical applications of linseed oil exploit its drying & polymerizing properties, the initial material is liquid or at least pliable and the aged material is rigid & water-repelling (hydrophobic) but not brittle.

Linseed oil is a special "drying” oil, i.e. in air it polymerizes into a solid form. Due to this linseed oil is used as an impregnator and varnish in wood finishing, as pigment binder in oil paints, as a plasticizer & hardener in putty and in the manufacture of linoleum

Linoleum = linum ("flax") and oleum ("oil")is an all vegetarian floor covering made from renewable materials such as solidified linseed oil (linoxyn), pine rosin, ground cork dust, wood flour, and mineral fillers such as calcium carbonate, most commonly on a burlap or canvas backing. Name derived from the Latin words linum("flax") and oleum ("oil"),.

1871 William Parnacott took out a patent for a method of producing linoxyn by blowing hot air into a tank of linseed oil for several hours, then cooling it in trays. Linoleum as a floor covering has been largely replaced with polyvinyl chloride (yet still known as "linoleum")

Linoleum was invented by Englishman Frederick Walton in 1855, who noticed the rubbery, flexible skin of solidified linseed oil (linoxyn). Walton accelerated the process by heating it with lead acetate and zinc sulfate. The oil formed a resinous mass into which cotton was dipped until a thick coating formed.

Task 5 : Fluorescent differentiation between butter & margarine

K. Swezey mentions this experiment in his book “ Chemistry Magic”, McGraw Hill 1956. Let us see whether it really works.

He says you can differentiate between margarine and butter using UV light. It is not obvious why this should be the case. You can google until you are green in the face and find no hint of fluorescing margarine. Now, this makes the stuff suitable for adventurous scientistas like us. We know that manufacturers add diacetyl & acetoin for butter taste & carotene for yellow color. Diacetyl is known to have some green fluorescence.

First, dissolve a little piece of butter in cigarette lighter fluid (like Zippo’s butane refill fluid, essentially a liquefied gas)) in a test tube.Repeat the same with margarine.

In room light both solutions appear similar. Under UV –however – the margarine fluoresces in a bright blue, butter not at all or slightly yellow.

Voila you can tell them pretenders that this was margarine and not butter that they use in your favorite ice cream.

“ I cannot believe it is not butter”

Paraffin & PEG are PCMs: phase change materials

sodium acetate heating pad. When the solution crystallises, it becomes warm.

PCMs are used to stabilize a specific transition temperature. In general, the temperature stays nearly constant during phase transitions. When the surrounding temperature rises above theirtransition temperature they absorb heat and melt, when the temperature falls they release heat and turn back to a solid.

A phase-change material (PCM) is a substance with a high heat of fusion which, melting and solidifying at a certain temperature, is capable of storing and releasing large amounts of energy.

Currently, a widespread PCM is paraffin

Some PCMs are very effective. They store 5 to 14 times more heat per unit volume than conventional storage materials such as water, or rock. PCMs can be incorporated into everything from shoes, winter jackets, and cushions to medical, aerospace, and automotive applications. Parrafin wax and polyethylene glycol (PEG) are two PCMs that can be incorporated into clothing fabric to maintain a comfortable temperature in cold weather

Does fat loss leave a bitter taste?

Rutin: citrus flavonoid glycoside found in buckwheat seeds, leaves & petioles of Rheum = rhubarb; glycoside = flavonol quercetin + rutinose. Comb. with cations to meditate transport into plant cell Antioxidant in humans attaches to Fe2+ to prevent binding to hydrogen peroxide & damag. free-radicals Rutin strengthens capillaries & reduce haemophilia& prevents unpleasant-looking venous edema of the legs,

Useful ingredient in fat burners: When "fat burner" is used on the label of a diet pill, the product is usually a brand namefor ephedra or ephedrine, coffeine, green tea extract & …naringin, sesamin = a lignan from sesame seed that binds receptor Peroxisome Proliferator-Activator Receptor Alpha

Naringin (Grape juice) major flavonoid glycoside that gives grapefruit its bitter taste & increases sensitivity of taste buds. Naringenin & hesperetin (aglycones) occur in citrus fruits acting as antioxidants, blood lipid-lowering, cholesterol-reducing, anticarcinogenic substances

Detergents and Polishes Soap is the oldest manufactured detergent. Before it people used plants with saponins like soap nuts etc to produce lather and also creams. Nowadays soap is replaced by synthetic detergents .

Romans used a paste made of Fuller’s earth ( a clay-like material able to absorb fats), soda (sodium carbonate) & urine for cleaning cloth & pots (see Pompeii). Pliny mentions the use of “sapo” as hair crème made from Beachwood ashes boiled in sheep tallow. Probably soap was discovered when animal sacrifices were saponified in wood ashes. Galen is first to mention washing with soap.

Ancient Egyptians used nitre (sodium carbonate) & castor oil to wash clothing but seemed to have kept their secret well as many others: batteries, glass making , cosmetics

Southern Europe (Spain) used barilla (ashes from seaweeds) with olive oil to make soap. Castile soap made in Venice and Castile.

Soap Manufacturing Soaps are Na or K salts of fatty acids with 12-18 C atoms. Na soaps are normally harder than K soaps. Highly saturated fats like tallow give harder soaps than low molecular weight fats like coconut oil.

Soaps are produced by the saponificastion of fat blends with an alkaline solution. The fats hydrolyse into glycerol & fatty acids. Brine or solid salt is then added to the solution. Since soap but not glycerol is insoluble in salt solution, soap will float on top. Glycerol will be in the salt solution & can be recovered from it.

Soap can be purified ( and made less alkaline) by dissolving it in hot water, boiling it for a short time and then salting it out. Last boiling is with added water to make the appearance less greasy.

Transparent soap can be produced by dissolving soap in ethanol or glycerol, evaporating it off before molding the soap (glycerin soap)

Soap Making Rendering & Clarifying of Fat: 1. Any oil can be used for making soap, diesel fuel, glycerin, nitroglycerin , candles, emulsifiers etc. If you use unpurified fat like kitchen drippings etc you should first render the fat. Rendering is the process of melting solid fat particles. Cut fat in pieces and let it melt. Remove solid particles = cracklings by straining. Unclear greasy mixtures can be clarified by placing the fat , an equal amount of water & 2 tablespoons of NaCl in the pan, and bring to a boil. When removing from heat cool and add cold water (one quart to 1 gallon of fat). Mixture will separate into 3 layers: on top purified or clarified fat, on the bottom water and in the center impurities.

What happens when we add HCl to soap and heat it up? Soap is the Na or K salt of fatty acids. The H+ ions will drive the Na or potassium ions out of their connection with the fatty acids & hence liberate fatty acids like oleic acid or stearic acid. Both are good emulgators and can also be used together with paraffin to make non-dripping candles.

Soap Making Alternatives How to make soap without heat:Henriques R (Z angew Chem 1895, 8, 721; 1896, 9, 221) reported that fats can be saponified readily at room temperature. The process may be carried out by dissolving 260 g of KOH in 250 ml water. After some minutes, a liter of the oil to be saponified is added to this solution. Ethanol (10 ml) is then added. This process was applied to fats containing easily altered fatty acids (i.e. conjugated fatty acids, highly unsaturated).

Separation of unsaponifiable matterAfter saponification, approximately half of the alcohol is removed under vacuum, the residue is diluted with water and the unsaponifiable matter (hydrocarbons, tocopherols, sterols) extracted by shaking with an organic solvent, diethyl ether or petroleum ether.

Recovery of acids from soaps

Fatty acids are liberated by the addition of mineral acid, usually a 10% excess of sulfuric acid or HCl. When very short-chain acids are present, the alcohol is removed prior acidification under vacuum with the addition of sufficient water to keep soaps in solution. If the amount of acids is important, the long-chain acids are separated from the aqueous medium by allowing the mixture to stand in the cold.

Plants that can be used as soap ersatz Plants that produce foam do not contain Na salts of fatty acids ( the manmade soap) but saponins - foaming terpenoids

The role of the foaming quality of saponins in plants is yet to be established. They are feeding repellents and also play a role to stabilize plant emulsions like latex etc.

Agave root, leaves & stem Jujuba or Zizyphus fruit Morning glory Ipomea plant ashes Pigweed Chenopodium root Pokeweed Phytolacca fruit Soapberry Sapindus berry Soapwort Saponaria root Yucca root Wild gourd Cucurbita fruit quinoa seeds lentil Lens culinaris seeds potatoes Solanum tuberosum fruit

Shepherdia soapberry is bitter

Zizyphus jujuba

SaponinsSaponins are secondary metabolites found in particular abundance in various plant species. Most of them are glycosides that form soap-like foaming when shaken in aqueous solutions. The aglycone (glycoside-free portion) of the saponins are termed sapogenins; it is either a triterpene or steroid.

Most saponins, which readily dissolve in water, are poisonous to fish. Therefore, in ethnobotany, saponins are primarily known for their use by indigenous people in obtaining aquatic food sources

Saponins in fish-poisoning plants Fish poisons = icthyotoxins or piscicides, occur in several plant species. Some chemicals like saponins will only stun the fish when it passes through the gills. The fish then floats to the surface for easy capture.

Saponins normally must enter the bloodstream to be toxic, but fish take in saponins directly into their bloodstream through their gills. Saponins cause the breakdown of red blood cells that help the toxin to spread quickly. Even though the effects of the poison are powerful, they are not usually fatal. Fish that are washed away into untainted water recover quickly.

The roots twigs and buds of the common horse chestnut Aesculus h. contains much saponin and was used to poison fish.

Another source of poisonous saponins is pokeweed Phytolacca americana. Indians use the leaves.

Other fish-poisoning plants Fish poisons = icthyotoxins or piscicides, occur in several plant species. Some chemicals will actually paralyze the CNS of fish when taken up through the gills. The fish does not recover.Not all fish poisons are saponins. A most frequently used one is an alkaloid called rotenone. Rotenone is extracted from the roots, seeds and leaves of tropical legumes. See 2 examples below. In mice it produced a model Parkinson’s disease.

Acacia ditricha seed pods are effective poison

Candles – the path to illuminationEarly candles were made from wicks covered with a mixture of beeswax & tallow. Tallow made candles are smoky & sputter.

1830 Industry provided a mixture of palmitic and stearic acid called “stearine” by hydrolysing animal fats. See making stearic acid: animal fat is hydrolyzed with acid or lime. The fatty acid mixture is dissolved in 1:9 water:methanol mixture before chilling and filtering oof the solid stearine, which crystallizes in the cold. You get two fractions: a solid one = steric acid and aliquid one = oleine. Stearine candles were very brittle and later paraffin wax was added. Paraffin is a byproduct of petroleum.

Modern candles. The paraffin contents was gradually increased until it completely replaced stearine paraffin candles

A candle relies upon capillary action to burn. The wick of a candle is made of many fibers wound closely together. The capillary spaces between the fibers draw molten wax upward to the flame.

Stearic acid comes in flakes

Candle MakingEarly candles were made from beeswax. Rind\se the empty comb and place it in a pan together with 2 parts of water to prevent the wax from catching fire. Heat until wax is melted & continue cooking for a while. You can add Paraffin wax of up to 90 % to make the candles cheaper. In the old days they added tallow from beef, and a half pound of saltpeter = nitrate.

Bayberry candles. Bayberries Myrica spp. grow in the sandy soil of the New England coastland to welcome the pilgrims. Gather berries in the fall, then boil them in water for two hours. Today bayberry bush are protected by law & you buy the ready wax from a berry farm.

Dipped candles: you need two tall beakers or pots: one filled with water (RT) & one filled with wax (160 F). You tie 3 wicks (10 cm longer than candle) to a stick and weigh their ends with washers. It takes 30-40 alternating dips in both liquids cooling and wax adding) to make a candle of 1 inch diameter.

Natural & Synthetic Waxes Beeswax was used for candles and polishes. Limited supply.

Carnauba wax is scraped from the leaves of the carnauba palm (Brazil). Sundreid leaves are beaten with sticks & boiling over open fire dislodges wax from the cuticles. grey natural product One tree gives approx. 170 g /year. Very hard wax. Upon cooling myricyl alcohol forms characteristic rings. Used for shoe polishes.

Raffia wax is from Raffia palm – the Madagascan sago palm which holds the record for having the largest leaves of all plants.

Candelilla wax is obtained from the stems of a Mexican weed in the Euphorbiaceae which is boiled with some water, brown aromatic wax is skimmed off the surface.

Paraffin waxes are distillation products of natural mineral oil – colourless, & odorless. They are soluble in organic solvents except ethanol & have unusually high melting point.