Index

Absolute configuration assignment, methods of, 182,234 benzoylglycerols

inversion, 243 determination, 58, 182, 269-280 diacylglycerols

determination, 269-280 nomenclature, 234

fatty acids anteiso, 59 branched-chain, 16-19,59 epoxy, 61 hydroxy, 61 isoprenoid, 18, 19 phytanic, 18, 19 pristanic, 18, 19

isopropylidene glycerols interconversion of enantiomers, 241

monoacylglycerols determination, 182, 269-280 nomenclature, 234

trlacytglycerols determination, 269-280 Fischer projection, 123, 234 nomenclature, 234 R/ S system, 234, 235 stereospecific (sn) numbering, 123, 235

Acetals, see Dimethylacetals

Acetic (ethanoic) acid positional distribution in triacylglycerols,

199 relative retention times, 13, 15

Acetolysis of glycerophospholipids, 125 of phosphatidylphenols, 125

Acetone, see Isopropylidene group and individual isopropylidene derivatives

Acetoxyacids equivalent chain length of esters, 38

Acetoxy acids (cont'd) gas-liquid chromatography, 37 thin-layer chromatography, 8

Acetylation of diacylglycerols, 127 of hydroxy acids, 37 of monoacylglycerols, 127

Acetylenic acids 14C-Iabeled, 89 equivalent chain length of esters, 31-36 gas-liquid chromatography, 30-36 identification, 30-36, 44 infrared spectroscopy, 180 mass spectrometry, 44 nuclear magnetic resonance spectroscopy, 57 occurrence, 30 thin-layer chromatography, 30

Actinomycin D inhibition of phosphatidic acid

phosphohydrolase, 318 Activation of fatty acids

enzymes of, 290 relative rates, 290 specificity, 290

Acylation acid anhydrides, 249, 250 acid chlorides, 248, 250

I-Acyl-sn-glycerols chemical synthesis, 255 cyclic phosphodiesters, 294

2-Acyl-sn-glycerols chemical synthesis, 256

3-Acyl-sn-glycerols chemical synthesis, 254 physical constants, 252, 253 table of, 252-254

Acyltransferases (see also Biosynthesis) l-acyl-sn-glycerol-3-phosphate

acyl acceptor specificity, 293 acyl donor specificity, 293

443

444

Acyltransferases (cont'd) l-acyl-sn-glycerol-3-phosphorylcholine

acyl acceptor specificity, 307 acyl donor specificity, 308

2-acyl-sn-glycerol-3-phosphorylcholine acyl acceptor specificity, 308, 309 acyl donor specificity, 309

I-acyl-sn-glycerol-3-phosphorylethanol-amine

substrate specificity, 307 2-acyl-sn-glycerol-3-phosphorylethanol­

amine substrate specificity, 308

diacylglycerol metabolic regulation, 317 stereospecificity, 271, 311, 312

sn-glycerol-3-phosphate acyl donor specificity, 292

monoacylglycerol acyl acceptor specificity, 300 acyl donor specificity, 30 I, 302 stereospecificity, 302, 303

monoalkenylglycerol, 311, 312 monoalkylglycerol, 311, 312

Additives (see also Antioxidants) antifoamers, 355 chelating agents, 355 emulsifiers, 354 pigments, 355 preservatives, 355 stabilizers, 355

Adenoma lipids composition of fatty acids cholesteryl esters, 419

phospholipids, 419 triacylglycerols, 419

man, 419 Adipose tissue lipids

composition of fatty acids chicken, 386 ox, 387, 392 pig, 387, 413 rabbit, 387

positional distribution of fatty acids beef, 217 cat, 217 dog, 217 horse, 217 man, 217 pig, 216, 218 rabbit, 217

Adrenal lipids composition of fatty acids

man, 419 pig, 218, 421 rabbit, 415 rat, 410, 411

AgNO, thin-layer chromatography alkenylacylglycerols

solvent systems, 137, 138 unsaturated, 137, 138

alkylacylglycerols solvent systems, 137, 138 unsaturated, 137, 138

diacylglycerols solvent systems, 137, 138 unsaturated, 137, 138

fatty acids acetylenic, 9, 10 conjugated, II cyclopentenyl, 9 cyclopropanoid, 9 epoxy,9, II ethylenic, 9, 10 geometric isomers, 9, 10 hydroxy, 9, II positional isomers, 9, 10 solvent systems, 10

monoacylglycerols, 138 triacylglycerols

positional isomers, 137 solvent systems, 137 unsaturated, 137

Alcohols gas-liquid chromatography, 131 thin-layer chromatography, 134

Alcoholysis acid catalyzed, 6 alkali catalyzed, 6 in presence of silica gel, 6, 7 of steryl esters, 6 of triacylglycerols, 6

Aldehydes (see also Dimethylacetals) RJ values, 134

I-Alkenyl-2-acyl-sn-glycerols chemical synthesis, 260 equivalent chain-length values, 150 gas-liquid chromatography, 149

I-Alkenyl-3-acyl-sn-glycerols equivalent chain-length values, 150 gas-liquid chromatography, 149

Alkenyldiacylglycerols RJ values, 134

I-Alkenyl-sn-glycerols equivalent chain-length values, 148 gas-liquid chromatography, 148 physical properties, 240 synthesis, 240 thin-layer chromatography, 134

I-Alkyl-2-acyl-sn-glycerols chemical synthesis, 260 equivalent chain-length values, 150 gas-liquid chromatography, 149 isomerization of, 267

Index

Index

I-Alkyl-2-acyl-sn-glycerols (cont'd) radioactive, 266, 267 Rf values of, 134, 136 synthesis of, 260, 261 thin-layer chromatography, 134, 136

I-Alkyl-3-acyl-sn-glycerols chemical synthesis, 261 equivalent chain-length values, 150 gas-liquid chromatography, 149 isomerization, 267 radioactive, 267 Rf values of, 134, 136 synthesis of, 261, 267 thin-layer chromatography, 134, 136

Alkylalkenyl-sn-glycerols chemical synthesis, 240 physical properties, 240

Alkyldiacylglycerols equivalent chain-length values, 155 gas-liquid chromatography, 155 occurrence, 260 Rf values of, 134

I-Alkyl-sn-glycerols equivalent chain-length values, 147 gas-liquid chromatography, 148 inversion of configuration, 241 physical properties of, 240 synthesis of, 240 thin-layer chromatography, 136

Allenic acids equivalent chain lengths of esters, 36 gas-liquid chromatography, 36 mass spectrometry, 44 thin-layer chromatography, 36

Almond oil fatty acid composition, 364

Analysis of lipids, see entries under specific techniques and under individual lipid classes

Animal fats composition of fatty acids

beef tallow, 373 chicken fat, 373 lard, 373 mutton tallow, 373

Antioxidants butylated hydroxyanisole (BHA), 355 butylated hydroxytoluene (BHl), 355 6-hydroxy-2,5, 7,8-tetramethylchroman-

2-carboxylic acid, 355 Antipodes, 234, 261 Aorta lipid

man composition of fatty acids, 416 positional distribution of fatty acids, 221

Arachidic (eicosanoic) acid occurrence, 358, 359, 363, 364

Arachidic acid (cont'd) positional distribution in triacylglycerols,

224-227, 229 Arachidonic (cis-5,cis-8,cis-II,cis-l4-

eicosatetraenoic) acid I'e-Iabeled, 90

445

positional distribution in triacylglycerols, 213, 215, 218, 221, 222, 343

tritiated, 98 Arsenite thin-layer chromatography (see also

Thin-layer chromatography) I-alkylglycerols, 136 2-alkylglycerols, 136 hydroxy acids, 9

Artifacts conjugated acids, 2 cyclic acetals of glycerol, 148 methoxy-substituted, 5 methyl esters, 393

Atlantic herring oil, see Herring oil Autoxidation, 2

Bacterial lipids, see Microbial lipids Beechnut oil

composition of fatty acids, 364 Behenic (docosanoic) acid

occurrence, 392, 397-399, 408, 411, 414, 419, 424, 433, 434

positional distribution in triacylglycerols, 222, 224,226

I-Benzyl-sn-glycerol interconversion of antipodes, 243 preparation, 243

3-Benzyl-sn-iIycerol interconversion of antipodes, 243 preparation, 239

Benzyl groups introduction, 239, 247 removal,247

Benzylidene groups hydrogenolysis, 256 introduction, 246 removal, 246

BHT, see Antioxidants Bile

composition of fatty acids cow, 407 dog, 407 man, 407 pig, 407 rat, 407 sheep, 407

Biosynthesis (see also individual lipid classes under Acyltransferases)

alkylacylglycerols, 30 I diacylglycerols

hepatic, 301, 303

Biosynthesis (cont'd) diacylglycerols (cont'd)

metabolic regulation, 315-317 microsomal, 301 monoacylglycerol pathway, 300, 301 mucosal, 300, 30 I neoplastic, 303 phosphatidic acid pathway, 291, 304, 305

dihydroxyacetone phosphate regulation of, 295, 298

fatty acids I'C-Iabeled, 99-100 3H-Iabeled, 101

methods of investigation cellular levels, 321, 322 kinetic problems, 322, 323 preparation of substrates, 322, 323

phosphatidic acid diacylglycerol kinase, 296, 297 dihydroxyacetone phosphate pathway,

295 glycerolphosphate pathway, 291 inhibition by monoacylglycerols, 315 metabolic regulation, 298, 315, 316 monoacylglycerol kinase, 296 utilization of glycerol, 298, 299

phosphatidylcholine radioactive, 10 I

triacylglycerols animal species specificity, 223, 385, 406 Ehrlich ascites, 311 hepatic, 311, 312 metabolic regulation, 310, 314-316 microsomal, 310, 311 monoacylglycerol pathway, 310, 313, 314 mucosal, 310, 311 phosphatidic acid pathway, 310, 313, 314 synthetase, 312 tissue specificity, 223

Blood pig

composition of fatty acids, 412 positional distribution of fatty acids, 212

Borate thin-layer chromatography (see also Thin-layer chromatography)

preparation of layers, 269 Rfvalues

alkylglycerols, 136 diacylglycerols, 136, 202, 269 hydroxy fatty acids, 9 monoacylglycerols, 136, 269 neutral lipids, 136

Brain composition of fatty acids

man, 416 sheep, 417

Branched-chain acids equivalent chain lengths of esters, 16-18

Branched-chain acids (cont'd) mass spectrometry, 41, 42

Index

nuclear magnetic resonance spectroscopy, 55,57

occurrence, 15-19 relative retention times, 13, 15 rotation of polarized light, 58, 59

Brassidic (trans-l3-docosenoic) acid equivalent chain lengths of esters, 23

Brazil nut oil composition of fatty acids, 364

Bromination of fatty acids, 83, 106 removal of bromine, 256 of triacylglycerols, 256

Butter composition of fatty acids, 372 modified milk, 372 nondairy creamers, 372

Butterfat triacylglycerols complexity, 208 composition of fatty acids, 372 deacylation with pancreatic lipase, 208 Grignard degradation, 153 liquid-liquid chromatography, 141 positional distribution of fatty acids, 209, 211 rotation of polarized light, 199 stereospecific analysis, 209, 211

t-Butyldimethylsilyl esters preparation, 6 stability, 6

t-Butyldimethylsilyl ethers preparation, 128 stability, 128, 199

n-Butyl esters of fatty acids, 346 of short-chain fatty acids, 346

Butyric (butanoic) acid deacylation by pancreatic lipase, 20 I, 208,

371, 372 gas-liquid chromatography, 13 occurrence, 209, 210 positional distribution in triacylglycerols, 208,

209, 210 steam distillation, 12

Calculations positional distribution of fatty acids

sn-I position, 205-206 sn-2 position, 206 sn-3 position, 206

structure of triacylglycerols I-random 2-random 3-random, 183 1,2-random 3-random, 183 1,2,3-random, 183

Capric (decanoic) acid occurrence, 358, 363, 371-373

llldu

Capric acid (cont'd) positional distribution, in triacylglycerols,

209, 210, 215, 221, 225 Caproic (hexanoic) acid

occurrence, 363, 371, 372 positional distribution, in triacylglycerols,

209, 210, 225 retention time, 13

Caprylic (octanoic) acid occurrence, 313, 363, 371 positional distribution in triacylglycerols,

209, 210, 225 Cardiolipin

composition of fatty acids chicken, 40 I man, 401 mitochondria, 426 rabbit, 401 rat, 401, 426 sarcoplasmic reticulum, 401 skeletal muscle, 40 I

Cat tissue lipids composition of fatty acids

erythrocytes, 394 positional distribution of fatty acids in

triacylglycerols adipose tissue, 217

Cashew nut oil composition of fatty acids, 364

Catalytic hydrogenation Undlar's catalyst, 51 location of double bonds, 50 palladium, 5 I reduction of ozonides, 51 Wilkinson's catalyst, 84

Cerotic (hexacosanoic) acid occurrence, 398, 433, 434 positional distribution in triacylglycerols, 229

Chaulmoogric [13-(2-cyclopentenyl)tridecanoic] acid,21

Cheeses composition of fatty acids

blue, 371 cheddar, 371 cottage, 371

Chemical degradation fatty acids

bromination, 106 Darzen-Mentzer, 106 Hunsdiecker, 106 Kuhn-Roth, 106, 107 Lemieux-Von Rudloff, 106 ozonolysis, 106 Schmidt reaction, 106

glycerolipids acetolysis, 125 Grignard, 126 hydrogenation, 127

Chemical degradation (cont'd) glycerolipids (cont'd)

hydrogenolysis, 125 methanolysis, 124 oxidative cleavage of double bonds, 126 thermal cleavage, 125

Chemical synthesis (see also Methods of derivation of lipids)

alkylacylglycerols l-alkyl-2-acyl-sn-glycerols, 260 l-alkyl-3-acyl-sn-glycerols, 261 3-alkyl-I-acyl-sn-glycerols, 261 3-alkyl-2-acyl-sn-glycerols, 260 l-alkyl-2,3-diacyl-sn-glycerols, 267 3-alkyl-l,2-diacylglycerols, 267 1,2-dialkyl-3-acyl-sn-glycerols, 267 2,3-dialkyl-l-acyl-sn-glycerols, 267 isotope-labeled, 267, 266

447

13C-labeled fatty acids, see Chemical synthesis of I'C-labeled fatty acids

I'C-labeled fatty acids addition of I'CN_, 92 carboxylation with I'C~, 91, 92 coupling of labeled intermediates, 91 Hunsdiecker degradation, 92 table of, 89 unsaturated, 93 Wittig reaction, 83, 93

diacylglycerols 1,2-diacyl-sn-glycerols, 256-260 1,3-diacyl-sn-glycerols, 261 2,3-diacyl-sn-glycerols, 256-260 isotope-labeled, 265, 266 table of, 259, 261

2H-labeled fatty acids azodicarboxylate reduction, 82 deuterohydrazine reduction, 81, 82 general synthetic reactions, 86 Kolbe reaction, 79 Undlar's reduction, 83 table of, 80, 81, 85 tris(triphenylphosphine )rhodium(I) chlorine

procedure, 84 Wittig reaction, 83, 93

3H-labeled fatty acids copper-chromite reduction of alkynoates,

95 diimide reduction, 95 disiamylborane reduction, 97 Undlar's reduction of polyacetylenes, 96 table of, 97, 98 Wilzbach procedure, 94

monoacylglycerols l-acyl-sn-glycerols, 249-256, 263 2-acyl-sn-glycerols, 256 3-acyl-sn-glycerols, 249-256, 263 isotope-labeled, 265 table of, 252, 253, 254

Chemical synthesis (COnl'd) monoalkenylglycerols

I-alkenyl-sn-glycerols, 240-241 I-alkenyl-sn-glycerols, 240, 241 table of, 240

monoalkylglycerols I-alkyl-sn-glycerols, 240-241 3-alkyl-sn-glycerols, 240-241 isotope-labeled, 267 table of, 240

phosphatidylcholine 2-[ 1-14C]stearoYI, 102 [3H]stearoyl, 102

triacylglycerols diacid enantiomers, 263, 264 isotope-labeled, 265 table of, 262-264 triacid, 263, 264, 266 unsaturated, 263, 266

Chestnut oil composition of fatty acids, 364

Chicken tissue lipids composition of fatty acids

adipose tissue, 386 liver, 386 skeletal muscle, 40 I

positional distribution of fatty acids in triacylglycerols

egg yolk, 220 Chirality, 234 Chiral shift reagents

enantiomeric shift differences, 279 tris(3-heptafluorobutyryl-d-<:amphorato )­

europium(III), 199, 278 Cholesterol

gas-liquid chromatography, 140, 349 quantitation, 348-350

Cholesteryl acetate Rf values, 134

Cholesteryl butyrate gas-liquid chromatography, 349 preparation, 348 quantitation, 348-350

Cholesteryl esters of long-chain acids composition of fatty acids

adenoma, 419 adrenals, 410, 415, 419 chylomicrons, 430 heart, 408 kidney, 408 lipoproteins, 429, 430 man, 393, 419, 429 pancreas, 393 plasma, 430 rabbit, 415 rat, 408, 410, 430 serum, 429

Index

Cholesteryl esters of long-chain acids (conl'd) composition of fatty acids (COnl'd)

skeletal muscle, 408 spleen, 415 testes, 415

gas-liquid chromatography, 140 Choline phosphotransferase

dietary regulation, 316 hormonal regulation, 317

Chromatography, see AgN03 thin-layer chromatography, Arsenite thin-layer chromatography, Borate thin-layer chromatography, Gas-liquid chro­matography, Liquid-liquid chro­matography, Reverse-phase chro­matography, and Thin-layer chromatography

Chylomicrons composition of fatty acids

dog, 405 man, 405 membrane, 405 oil phase, 405 rat, 405, 430

structure of triacylglycerols rat, 215 sheep, 215

Circular dichroism curves 1,2-diacetyl-3-myristoyl-sn-glycerol, 276 1,2-dimyristoyl-sn-glycerol, 276 1,2-dipalmitoyl-sn-glycerol, 274 enantiomeric triacylglycerols, 198 1,2-isopropylidene-'3-palmitoyl-sn-glycerol,274 3-palmitoyl-sn-glycerol, 274

I3C-Iabeled fatty acids (see also Chemical synthesis)

analysis of, 107 biosynthesis, 91 gas-liquid chromatography, 108 mass spectrometry, 107-110 nuclear magnetic resonance spectroscopy,

112-115 table of, 88 utilization in metabolic studies, 88

14C-Iabeled fatty acids (see also Chemical synthesis)

analysis of, 102-107 biosynthesis, 99, 100 gas-liquid chromatography, 105 scintillation counting, 102 table of, 89, 101 uniformly labeled, 101

Clofenapate [sodium 4-(4'-chlorophenyl)­phenoxyisobutyrate]

inhibition of dihydroxyacetonephosphate acylation, 319

inhibition of glycerophosphate acylation, 319

lrulex

Clofibrate (ethyl-L-p-chlorophenoxyisobutyrate) effect on lipid biosynthesis, 319 hypolipidemic effect, 319 inhibition of fatty acid synthesis, 319 inhibition of glycerophosphate dehydrogenase,

319 Coberine oil

composition of fatty acids, 363 Cocoa butter

composition of fatty acids, 343, 363 deacylation with pancreatic lipase, 20 I positional distribution of fatty acids, 224,

225 Coconut oil

composition of fatty acids, 363 deacylation with pancreatic lipase, 20 I positional distribution of fatty acids, 224, 225

Cod liver oil composition of fatty acids, 219 deacylation with pancreatic lipase, 201 positional distribution of fatty acids, 219

Confectionery products composition of fatty acids

coberine oil, 363 cocoa butter, 363 coconut oil, 363 illipe butter, 363 palm kernel oil, 363 palm oil, 363 shea nut, 363

Conjugated linoleic (9, II-octadecadienoic) acid equivalent chain lengths of esters, 27, 29

Cooking oils composition of fatty acids

commercial, 366 household, 366

Corn oil composition of fatty acids, 358 positional distribution of fatty acids, 225 sources, 351

Coryolic (13-L-hydroxy-cis-9,trans-ll­octadecadienoic) acid

occurrence, 224 positional distribution in triacylglycerols, 224

Cotton effect, 276, 277 Cottonseed oil

composition of fatty acids, 358 sources, 357

Countercurrent distribution of fatty acids, 12

Creamers composition of fatty acids

dairy creamers, 372 nondairy creamers, 372

Crystallization fatty acids

with acetone, 12

Crystallization (cont'd) fatty acids (cont' d)

with nitromethane, 12 urea adduct formation, 12

Cycloheximide

449

inhibition of diacylglycerol acyltransferase, 318 Cyclopentene acids

chaulmoogric, 21 equivalent chain lengths of esters, 21 gorlic, 21 hormelic, 43 hydnocarpic, 21 mass spectrometry, 42, 43 occurrence, 20, 21

Cyclopropane acids equivalent chain lengths of esters, 20 infrared spectroscopy, 53 mass spectrometry, 42 nuclear magnetic resonance spectroscopy, 57 reaction with boron trifluoride/methanol, 42

Cyclopropene acids addition of methanethiol, 42 mass spectrometry, 42 ozonolysis, 42 reaction with silver nitrate, 20 reduction, 20, 42

Dairy products composition of fatty acids

butter, 372 cheese, 371 milk fat, 372

Deacylation methods chemical

Grignard, 126, 187, 200, 202 hydroxide, 2 methoxide, 6

enzymic, see Lipases decanoic acid, see Capric acid

Dehydrogenases Chlorella

fatty acid specificity, 63 positional specificity, 63 stereospecificity, 63

hen liver fatty acid specificity, 63 positional specificity, 63 stereospecificity, 63

Depot fat, see Adipose tissue lipids Derivation of lipids, see Methods of

derivation Determination of glycerol

chemical, 129 enzymatic, 130 gas-liquid chromatographic, 129, 130 mass spectrometric, 130

Deuterohydrazine reduction 81, 82

450

Deuterolipids (see also 2H-labeled fatty acids and entries under individual lipids)

acylglycerols biosynthesis, 50 chemical synthesis, 265

fatty acids analysis of, 107 gas-liquid chromatography, 108 infrared spectroscopy, 111-112 isotope effects, 87 mass spectrometry, 49 monounsaturated, 82 nuclear magnetic resonance spectroscopy,

112-115 perdeuterated, 81, 82, 85 polyunsaturated, 84, 85 saturated, 79 synthesis, 78, 79, 83, 84, 86, 93 table of, 80, 81, 85

1,2-Diacetyl-3-methoxypropane gas-liquid chromatography, 130 as internal standard, 130 mass spectrometry, 130 preparation, 130

Diacylglycerol (see also Biosynthesis, Chemical synthesis, Gas-liquid chromatography, Stereospecific analysis, and Thin-layer chromatography)

acyltransferase occurrence, 310 regulation, 310, 317 substrate specificity, 271, 311, 316

kinase occurrence, 204, 296, 297 regulation, 296, 297 substrate, 204, 270, 297 specificity, 297

1,2-Diacyl-sn-glycerols biosynthesis, 299, 300 chemical synthesis, 256-258, 260 molecular species, 256, 257 optical rotatory dispersion, 259 other physical properties, 259 Rf values, 134 table of, 259

1,3-Diacyl-sn-glycerols chemical synthesis, 261 physical properties, 259, 261 piezoelectric effect, 263 Rf values, 134 table of, 259, 261

2,3-Diacyl-sn-glycerols biosynthesis, 304 chemical synthesis, 256-258 molecular species, 259 physical properties, 259 specific rotation, 259 table of, 259

1,2-Diacyl-sn-glycerol-3-iodohydrins chemical synthesis, 260 molecular species, 260 physical constants, 260 specific rotation, 260 table of, 260

lrulu

Diacylglyceryl ethers, see Alkylacylglycerols 1,2-Dialkyl-sn-glycerols

chemical synthesis, 240, 261 occurrence, 260 physical constants, 240

2,3-Dialkyl-sn-glycerols chemical synthesis, 261

Diethylenic fatty acids cis,cis-isomers, 24, 25, 30 cis,trans-isomers, 26 conjugated, 27, 29 dimethylene interrupted, 25 equivalent chain length of esters, 24-28 monomethylene interrupted, 24 polymethylene interrupted, 26 trans,trans-isomers, 24, 25, 30

Diglycerides, see Diacylglycerols Dihydroxyacetone phosphate

acylation, 295 acyl donor specificity, 295

Dimethylacetals formation, 8, 131 occurrence, 387, 397, 401, 421 Rf values, 134

Dimorphecholic (9-hydroxy-trans-l0,trans-12-octadecadienoic) acid

equivalent chain lengths of esters, 47 mass spectrometry, 47

Docosahexaenoic acid equivalent chain lengths of esters, 28 positional distribution in triacylglycerols,

213, 219 resistance to pancreatic lipase, 3

Docosapentaenoic acid equivalent chain lengths of esters, 28 14C-labeled, 90

Docosatetraenoic acid equivalent chain lengths of esters, 28 U_14C-labeled, 101

Dodecanoic acid, see Lauric acid Dog tissue lipids

composition of fatty acids adipose tissue, 413 bile, 407 chylomicrons, 405 erythrocytes, 394 lung, 388 milkfat, 403

positional distribution of fatty acids in triacylglycerols

adipose tissue, 217

Index

Double bonds conjugation, 52 hydroxylation, 52 isomerization, 2 location

catalytic reduction with deuterium, 51 epoxide formation, 45 oxidative cleavage, 51 oxonolysis, 51 pyrrolidide mass spectrometry, 43

protection, 2 reduction, 51

Egg yolk triacylglycerols

positional distribution of fatty acids, 220

unsaturation classes, 220 Ehrlich ascites cells

acyltransferase diacylglycerol, 303, 304 monoacylglycerol, 303, 304

composition of fatty acids, 422 Eicosadienoic acid

I'e-Iabeled, 90 equivalent chain length of esters, 27 positional distribution in triacylglycerols,

218,222 tritiated, 98

Eicosapentaenoic acid UYe-Iabeled, 101 equivalent chain length of esters, 28 isomers, 101 positional distribution in triacylglycerols,

213, 219 resistance to pancreatic lipase, 3

Eicosatetraenoic acid, see Arachidonic acid Eicosatrienoic acid

I'e-Iabeled, 90, 10 I equivalent chain length of esters, 28 positional distribution in triacylglycerols,

213, 218 Eicosenoic acid

I'e-Iabeled, 90, 98 equivalent chain length of esters, 23 occurrence, 358, 359 positional distribution in triacylglycerols, 210,

218, 219, 221, 222, 226 Elaidic (trans-9-0ctadecenoic) acid

deuterated, 113, 114 equivalent chain length of esters, 23 melting point, 342 selective acylation, 308

Elaidolinolenic (trans-9,trans-12,trans-15-octadecatrienoic) acid

equivalent chain length of esters, 24 occurrence, 25, 26

451

Eleomargaric (9-trans,12-trans-octadecadienoic) acid

equivalent chain length of esters, 24 occurrence, 25, 26

a-Eleostearic (cis-9,trans-ll,trans-13-octadecatrienoic) acid

equivalent chain length of esters, 29 occurrence, 27, 29

J3-Eleostearic (trans-9,trans-ll,trans-13-octadecatrienoic) acid

equivalent chain length of esters, 29 occurrence, 27, 29

Emulsifiers, 344 Enantiomers

of fatty acids absolute configuration, 16-19, 61 optical rotation, 58-61

of acylglycerols absolute configuration, 234 optical rotation, 124, 240, 251-254,

259-262, 264 Enzymatic acylation of lipid substrates

difficulties, 322-324 effect of concentration of substrate, 323 endogenous substrates, 323 exogenous substrates, 323 kinetics, 323

Epidermal cells composition of fatty acids

of different animal species, 398 of different lipid classes, 398

Epoxidation, 45, 52 Epoxy acids

equivalent chain lengths of esters, 39 hydrolysis of lipids containing, 3, 6 infrared spectroscopy, 54 mass spectrometry, 45 occurrence, 36 optical rotation, 61 stereochemistry, 61 synthesis, 52 thin-layer chromatography, 9 transesterification, 6

Equivalent chain length alkenylacylglycerols

acetates, 150 t-butyldimethylsilyl ethers, 149 trimethylsilyl ethers, 150

alkylacylglycerols acetates, 150 t-butyldimethylsilyl ethers, 149 trimethylsilyl ethers, 150

calculation, 144 definition, 144 diacylglycerols

acetates, 135 t-butyldimethylsilyl ethers, 152 trimethylsilyl ethers, 150

452

Equivalent chain length (cont'd) fatty acids

acetylenic, 31 anteiso, 17 cyclic, 19-21 cyclopropanoid, 19, 20 diastereoisomers, 18 diethylenic, 24 dimethyl, 17 epoxy, 39 iso, 17 isoprenoid, 17, 18 methyl esters, 147 monoethylenic, 21, 22 monomethyl, 15-17 neo, 17 phytanic, 18, 19 polyethylenic, 25-27 pristanic, 18 triethylenic, 28 trimethyl, 17 trimethylsilyl esters, 5

monoacylglycerols acetates, 135, 147 isopropylidenes, 148 trimethylsilyl ethers, 147

monoalkenylglycerols acetates, 147 isopropylidenes, 148 trimethylsilyl ethers, 147

monoalkylglycerols acetates, 135, 147 isopropylidenes, 148 trimethylsilyl ethers, 147

Erucic (cis-13-docosenoic) acid equivalent chain length of esters, 23 occurrence, 359 positional distribution in triacylglycerols, 219,

224,226 Erythrocytes

composition of fatty acids, 394 different animal species, 394

Essential fatty acids arachidonic, 342, 389, 409 linoleic, 342, 389, 409 nutritional importance, 342

Esterification of acids, see Methods of derivation of lipids

Estolides mass spectrometry, 187 pancreatic lipase hydrolysis, 20 I, 234 structure, 187, 224, 227 thin-layer chromatography, 137

Ethylenic acids, see Fatty acids Extraction of tissues

animal, 344-346 artifact formation, 345-346 foods, 344-346

Extraction of tissues (cont'd) plant, 345, 346, 352

Index

prevention of contamination, 344-346 recommended procedures, 344-346 removal of nonlipid contaminants, 345-346 solvents, 131, 344, 345 total fat

AOAC method, 344, 345 diethyl ether extraction, 344, 345 petroleum ether extraction, 344, 345

total lipid Bligh and Dyer, 131, 345 CFR method, 344, 345 Fo1ch, 345, 346

Fat contribution of major food groups beans, 342 butter, 342 cereal, 342 dairy products, 342 eggs, 342 fats and oils, 342 fish, 342 fruits, 342 meats, 342 nuts, 342 soy products, 342

Fatty acids (see also Acetylenic, Allenic, Branched-chain, Conjugated, Cyclo­propane, Cyclopropene, Epoxy, Free and Hydroxy acids)

activation relative rates, 289, 290

content of animal fats, 373 butter, 372 cheese, 371 confectionary fats, 363 nuts, 365 seed oils, 358, 359 soy lecithin, 343

countercurrent distribution, 12 gas-liquid chromatography

accuracy, 156-158, 343, 347, 384 capillary column, 14 conventional column, 147, 347 equivalent chain length of esters, 147 liquid phases, 347 preparative, II quantitation, 347-348 relative retention times, 13, 147, 347

geometric isomers, 9, 10 hydroxamate estimation, 52 infrared spectroscopy, 53 location of 14C, 106 location of deuterium, 107-115 mass spectrometry, 40-48

Index

Fatty acids (cont'd) melting points, 342 nomenclature, 342, 343 nuclear magnetic resonance spectroscopy,

55,57 nutritional importance, 342 positional isomers, 8, 10 positional distribution in triacylglycerols,

209-229 relative rates of enzymic esterification, 290 reversed-phase chromatography, 12 steam distillation, 12 thin-layer chromatography (see also AgN03

thin-layer chromatography, Arsenite thin­layer chromatography, and Borate thin­layer chromatography)

Rf values, 134 ultraviolet spectroscopy, 52, 53

Fatty alcohols acetylation, 131 t-butyldimethylsilylation, 131 gas-liquid chromatography, 131 generation, 131 mass spectrometry, 131 Rf values, 134, 136 trimethylsilylation, 131

Feces composition of fatty acids

man, 437 rat, 435

Fenfluramine [2-ethylamino-I-(m-trifluoro­methylphenyl) ]propane

inhibition of glycerolipid synthesis, 319 Filbert nut

composition of fatty acids, 364 Fish lipids (see also Marine oils)

composition of fatty acids lake fish, 21 sea fish, 372-374

cyclic acids, 21 Flame ionization detector response factors

cholesteryl esters, 157 triacylglycerols, 157 tridecanoylglycerol, 157 trimethylsilyl esters of fatty acids, 157 trimethylsilyl ethers

ceramides, 157 cholesterol, 157 diacylglycerols, 157 monoacylglycerols, 157

Formic (methanoic) acid relative retention times, 155

Free fatty acids (see also Fatty acids) composition of

adipose tissue, 392 feces, 433 Graafian follicles, 391 heart, 408

Free fatty acids (cont'd) composition of (cont'd)

kidney, 408 liver, 408 ovaries, 391 pancreas, 393 skeletal muscle, 408 thyroid, 392 testes, 390

453

determination, see under specific methods of analysis

French dressing composition of fatty acids, 355 general composition, 355

Functional group analysis cyclopropene ring, 52 ester bonds, 52 hydroxyl, 52 keto, 52 trans double bonds, 52

Gas-liquid chromatography (see also Radio-gas-liquid chromatography)

acylalkylglycerols, 142-144 alkylacylglycerols, 154 S-alkylglycerols, 148 campesteryl butyrate, 349 carbon-number resolution, 154 cholesteryl butyrate, 349 diacylglycerols

acetates, 149, 153 t-butydimethylsilyl ethers, 149 calculation of polarity factor, 154 calculation of relative retention times, 152 choice of derivative, 147, 149 choice of liquid phase, 142, 143, 147, 149 equivalent chain-length values, 135, 144, 149,

150, 152 relative retention times, 143, 145, 152 separation factors, 143, 145, 149, 150 trimethylsilyl ethers, 326

fatty acids acetoxy, 37, 38 acetylenic, 31-36 allenic, 36 branched-chain, 13, 15-18 choice of liquid phase, IS, 347 conjugated, 29 cyclopropene, 20 diethylenic, 24-27 epoxy, 39 equivalent chain-length values, 16-18,20-29,

31-36, 38, 39 free, 13, 15, 38 general procedure, 347 hydroxy, 38 keto, 38

454

Gas-liquid chromatography (cont'd) fatty acids (cont'd)

monoethylenic, 21-23 polyethylenic, 28 relative retention times, 13, IS, 147 saturated, 14-20 short-chain, 13, IS trans-isomer resolution, 22

monoacylglycerols acetates, 144, 147 choice of derivatives, 144 choice of liquid phases, 145 equivalent chain-length values, 147 isopropylidenes, 144, 178 relative retention times, 147 resolution of isomers, 145 separation factors, 145 trifluoroacetates, 144 trimethylsilyl ethers, 144, 146, 147

monoalkylglycerols acetates, 147, 148 choice of derivatives, 148 choice of liquid phases, 142 equivalent chain-length values,

147 isopropylidenes, 148 relative retention times, 147, 148 resolution of isomers, 418 trifluoroacetates, 144 trimethylsilyl ethers, 147, 148

neutral lipids profiles, 140 response factors, 157

quantitation acylglycerols, 156-157 fatty acids, 383, 384 relative response factors, 156,

157 sterols, 349

response factors, IS sitosteryl butyrate, 349 total lipid profiles, 140 triacylgiycerols

acetoxytriacylglycerols, ISS alkylacylgiycerols, ISS branched-chain, 154, ISS capillary columns, 154 choice of liquid phase, 154 conventional columns, 154 epoxy, ISS hydrogenated, 154 nonpolar liquid phases, 154 polar liquid phases, ISS relative recoveries, 156, 157 relative retention times, ISS separation by carbon number, 154,

ISS separation by unsaturation, 154, ISS

use of internal standards, 156, 157

lllllu

Gas-liquid chromatography / mass spectrometry (see also Mass spectrometry and individual listings of lipid classes)

tdkylacylgiycerols, 176 diacylglycerols

acetates, 171, 172 t-butyldimethylsilyl ethers, 173, 174,

176 positional isomers, 175 trimethylsilyl ethers, 172-174 underivatized, l71-173 unsaturated, 174-175

fatty acids I3C-Iabeled, 108-109 t-butyldimethylsilyl esters, 5 deuterated, 108 methyl esters, 108 perdeuterated, 108 stable isotope-labeled, 108 trimethylsilyl esters,S

monoacylglycerols acetates, 159 trimethylsilyl ethers, 160-163

monoalkenylglycerols cyclic acetals, 169 trimethylsilyl ethers, 169-171

monoalkylglycerols acetates, 166 dimethoxy derivatives, 163, 164 isomeric, 168-169 trimethylsilyl ethers, 166-169

triacylglycerols, 179 Glycerol

assay of, 129, 130 dehydrogenation, 130 kinase, 130 triacetyl, 129

sn-Glycerol-l-benzyl ether, 239 sn-Glycerol-3-benzyl ether, 239 sn-Glycerol-I,2-isopropylidene, 238 sn-Glycerol-2,3-isopropylidene, 238 sn-Glycerol-3-phosphate

acyltransferase acyl donor specificity, 291, 292 inhibition by clofibrate, 319 microsomal, 292 mitochondrial, 295

levels effect of clofibrate, 319 effect of epinephrine, 317 effect of nutritional state, 316

Glycosphingolipids composition of fatty acids

epidermal cells, 398 man, 398 pig, 398

Goat milk positional distribution of fatty acids in

triacylglycerols, 210, 211

l1Ulex

Gorlic [13-(2-cyclopentenyl)-6-tridecenoic] acid,21

Graafian follicles composition of fatty acids

cow, 391 pig, 391

Grignard degradation generation of diacylglycerols, 126, 187,200,

202 procedure, 202

Guinea pig tissue lipids composition of fatty acids

erythrocytes, 394 lung, 388 milk,403 pancreas, 393

Hamster mucosal lipids biosynthesis

alkylacylglycerols, 301 diacylglycerols, 301

Harbor seal oil composition of fatty acids, 219 positional distribution of fatty acids, 219

Heart lipids composition of fatty acids

man, 416 pig, 414 rabbit, 415 rat, 408, 410 sheep, 414

positional distribution of fatty acids in triacylglycerols

man, 221 pig, 218

Heneicosanoic acid 13C-labeled, 88 I'C-Iabeled, 89 perdeuterated, 81

Heptadecanoic acid deuterated, 80 as internal standard, 384

Herring oil composition of fatty acids, 219 positional distribution of fatty acids,

219 resistance to hydrolysis with pancreatic lipase,

3,200,201 Hexadecanoic acid, see Palmitic acid 1-Hexadecanoy 1-2-butanoy l-rac-g1ycerol

equivalent chain-length values, 135 Rf values, 135

Hexafluoroacetate trihydrate, 277, 278 'H-Iabeled fatty acids (see also Chemical

synthesis) biosynthesis, 85 mass spectrometry, 107-110 table of, 80, 81, 85

3H-labeled fatty acids (see also Chemical synthesis)

biosynthesis, 99, 101 scintillation counting, 102 table of, 97, 98

455

Hormelic [15-(2-cyclopentenyl)pentadecanoic] acid, 43

Hormonal factors effect on g1ycerolipid biosynthesis, 317

Hormone sensitive lipase metabolic control, 327 occurrence, 327

Horse depot fat positional distribution of fatty acids, 217

Human tissue lipids composition of fatty acids

adipose tissue, 416, 419 adrenals, 419 aorta, 416 bile, 407 brain, 417, 427 chylomicrons, 405 cultured cells, 423 epidermal cells, 398 erythrocytes, 394 fecal lipids, 433 heart muscle, 416 lipoproteins, 429 liver, 416 lung, 388 milk fat, 403 myocardium, 416 pancreas, 393 plasma, 222 skeletal muscle, 401, 418 skin, 423, 432 spermatozoa, 397

positional distribution of fatty acids in triacylglycerols

adipose tissue, 221 aorta, 221 heart muscle, 221 lipoproteins, 220, 222 liver, 221 milk fat, 221 plasma, 221

Hydnocarpic [11-(2-cyclopentenyl)undecanoic] acid,21

Hydrases positional specificity, 63 sources of, 62 substrate specificity, 62

Hydrazine reduction double bonds, 51 triple bonds, 83

Hydrocarbons Rf values, 134

Hydrogenation (see also Chemical synthesis) triacylglycerols, 127

456

Hydrogenation (cont'd) triacylglycerols (cont'd)

nonselective, 353 selective, 353

unsaturated fatty acids, 81-84, 94-99 Hydroxy fatty acids

Coryolic, 224 equivalent chain length of esters, 38 optical rotation, 60 Rjvalues, 8 thin-layer chromatography, 8, II

Hyperlipoproteinemia triacylglycerols

positional distribution of fatty acids, 222

Illipe butter composition of fatty acids, 363

Infrared spectroscopy acyl glycerols

chain length, 180 geometric configuration, 180 positional isomers, 180

band assignments, 180 fatty acids

band assignments, 53, 54 conjugated, 180 deuterated, III, 112 geometric isomers, 112, 180 solid state, 112 substitution products, 180

Intestinal enzymes acyltransferases

diacylglycerol, 301 monoacylglycerol, 304

kinase diacylglycerol, 200, 270 glycerol, 130

rat, 215, 303, 305 sheep, 215 synthetase

triacylglycerol, 215, 303, 304 transacylase

monoacylglycerol, 30 I, 304 Isobutyric (2-methylpropanoic) acid

retention times, 13 Isolation of lipid classes

acylglycerols gas-liquid chromatography, 144 silicic acid/boric acid column chromatog­

raphy, 268 thin-layer chromatography, 267, 268

fatty acids crystallization, 12, 268 distillation, 12, 268 preparative chromatography, II, 268

Isopropylidene group introduction, 127, 236, 245 removal, 239, 245

1,2-Isopropylidene-3-acyl-sn-glycerols chemical synthesis, 250 physical constants, 251, 254 table of, 251, 254

1,2-Isopropylidene-sn-glycerol chemical synthesis, 235, 238, 239

Index

conversion into 2,3-isopropylidene-sn-glycerol, 241

2,3-Isopropylidene-I-acyl-sn-glycerols chemical synthesis, 250 physical constants, 251 table of, 251

2,3-Isopropylidene-sn-glycerols chemical synthesis, 236, 238, 239

Isovaleric (3-methylbutanoic) acid gas-liquid chromatography, 13, 15 retention time, 13, 15

Keto acids equivalent chain length of esters, 39 natural, 38 synthetic, 38, 39

Kidney lipids composition of fatty acids

pig, 421 rat, 408 sheep, 414

positional distribution of fatty acids, 218 Kinase

diacylglycerol, 200, 270 glycerol, 130 monoacylglycerol, 296

Kinetic problems enzyme solubility, 322, 323 .ubstrate solubility, 323

Lauric (dodecanoic) acid 14C-Iabeled, 89 dideuterated, 80 gas-liquid chromatography, 147 occurrence, 358, 359, 363-365, 371-373 positional distribution in triacylglycerols, 209,

210,215,221,224,225 tritiated, 97

Lecithin, see Phosphatidylcholine Lignoceric (tetracosanoic) acid

gas-liquid chromatography, 392, 394, 398, 399,411,419,421,422,433,434

positional distribution in triacylglycerols, 229 Linoleic (cis-9 ,cis-12-octadecadienoic) acid

l3C-Iabeled, 88, 109 14C-Iabeled, 89, 101 equivalent chain length of esters, 24 isomeric, 85, 98 occurrence, 358, 359, 363-367, 369-373 perdeuterated, 85

Index

Linoleic acid (cont'd) positional distribution in triacylglycerols, 209-

215,217-222,225-227,229 thin-layer chromatography, 10 tritiated, 98

Linolelaidic (trans-9 ,trans-12-octadecadienoic) acid

equivalent chain length of esters, 24 selective acylation, 309 thin-layer chromatography, 9, 10

Linolenic ( cis-9 ,cis-12,cis-15-octadecatrienoic) acid

13C-Iabeled, 88, 110 I4C-Iabeled, 89, 10 I equivalent chain lengths of esters, 28 occurrence, 358, 359, 363-367, 369-373 perdeuterated, 85 positional distribution in triacylglycerols, 210,

213,215,217,218,221,222,225-227 selective acylation of positional isomers, 309 thin-layer chromatography, 9, 10

'Y-Linolenic (cis-6,cis-9 ,cis-12-octadecatrienoic) acid

equivalent chain length of esters, 28 thin-layer chromatography, 9, 10 tritiated, 98

homo--y-Linolenic (cis-8,cis-11 ,cis-l4-eico-satrienoic) acid

equivalent chain length of esters, 28 positional distribution in triacylglycerols, 227 thin-layer chromatography, 9

Linseed oil positional distribution of fatty acids, 225

Lipases (see also Phospholipases and entries under individuallipases)

castor bean, 3 Geotrichu11J candidum, 3, 64 hepatic, 3, 270, 327 hormone-sensitive, 3, 327 lipoprotein, 3, 64, 270, 325 monoacylglycerol, 5, 328 pancreatic, 3, 64, 270, 324 pharyngeal, 3, 270, 324 Rhyzopus arrhizus, 3 stereospecificity, 64, 270

Lipoprotein lipase assay, 271, 325 fatty acid specificity, 325 hydrolysis of alkylacylglycerols, 326 positional specificity, 325, 326 stereospecificity, 371, 325, 326

Lipoproteins composition of fatty acids

man, 429 rat, 430

positional distribution of fatty acids man, 222

Lipoxidases assay of cis,cis-polyunsaturation

fats, 351 flaxseed, 62 margarines, 350 meats, 351 peanut, 62 procedure, 350 shortenings, 351 vegetable oils, 350

calculation, 351 specificity,

positional, 62, 351 stereo-, 62 substrate, 61, 62, 350

sources of, 62

Liquid-liquid chromatography diacylglycerols, 141, 142 fatty acids, II high resolution, 141 with mass spectrometry, 141 triacylglycerols, 141

Liquid phases McRynolds constants, 142 nonpolar

457

Apiezon L (ApL), 12, 16, 18,20,22,29,31-35,39

Apiezon M (ApM), 17 Dexil (carborane alkylsiloxane), 154 JXR (methylsiloxane), 153, 154 OV-17 (50% phenylmethylsiloxane), 154 OV-IOI (methylsiloxane), 25, 33, 154 Poly-S179 (polyamide), 154 QF-I (fluoroalkylsiloxane), 38 SE-30 (methylsiloxane), 15, 17,25,32,33,38,

154 XF-1I50 (silicone fluid), 22, 24, 29

polar BDS (butanediol succinate), 16, 18,23,27,29 Carbowax (polyethyleneglycol), 23, 24, 25 CDX (cyclodextrin esters), 23, 27, 28, 31, 36 CN (cyanoalkylsiloxane), 24, 31 DEGS (diethyleneglycol succinate), 15, 17,

22-29,31-36,39 EGA (ethyleneglycol adipate), 24 EGS (ethyleneglycol succinate), 23, 24,27,

28,31,36,38 EGSS-X (ethyleneglycolsuccinate-siloxane),

15, 23,27,28, 155 FFAP (free fatty acid phase), 25, 32, 33 NPGA (neopentyglycol adipate), 24, 29 NPGS (neopentylglycol succinate), 20, 22,

24,31 PEGA (polyethyleneglycol adipate), 16, 17,

20, 25, 28, 33 PPE (polyphenyl ether), 15, 24, 26, 29, 31 Reoplex (polypropyleneglycol adipate),16

458

Liquid phases (cont'd) polar (cont' d)

Silar IOC (100% cyanopropylsiloxane), 25, 30, 32, 33, 34, 43

Silar 5CP (50% cyanopropyl, 50% phenyl­siloxane), 145-147, 150, 151, 155, 163

SP-l000 (Carbowax plus terephthalic acid), 148

TCPE (tetracyano ethylated pentaerythritol), 22,24,29

tricresyl phosphate, 13 trimer acid, 13 TXP (trixylenyl phosphate), 15 Ucon-LB-550-X (polypropyleneglycol), 13 Versamid (polyamide resin), 16 XE-60 (cyanoalkylsiloxane), 21, 22, 25, 26,

29,33,35 Liquid scintillation counting

radioactive carbon, 102 scintillation solvents, 102 tritium, 102

Liver lipids composition of fatty acids

chicken, 386 man, 416 pig, 386, 412 rabbit, 415 rat, 214, 386, 408, 410 sheep, 414

positional distribution in triacylglycerols man, 221 pig, 212-214, 221 rabbit, 213 rat, 213 sheep, 213

Lobster oil composition offatty acids, 219 positional distribution of fatty acids, 219

Lung lipids composition of fatty acids

chicken, 388 cow, 388 dog, 388 frog, 388 guinea pig, 388 man, 388 mouse, 388 rabbit, 388 rat, 388 sea lion, 388 turtle, 388

Lymphocytes composition of fatty acids

calf, 395 phosphatidylcholine, 395 phosphatidylethanolamine, 395 pig, 395 rabbit, 395

Macadamia oil composition of fatty acids, 365

Mackerel oil composition of fatty acids, 219 positional distribution of fatty acids, 219

Maize oil, see Com oil D-Mannitol

1,2:5,6-diisopropylidene, 237 as source of enantiomeric glycerols, 235

L-Mannitol 1,2:5,6-diisopropylidene, 237 formation from quebrachitol, 236, 237 as source of enantiomeric glycerols, 235

Margaric acid, see Heptadecanoic acid Margarines

composition of fatty acids diet, 370 dietetic margarine, 370 liquid, 370 mayonnaise, 370 salad dressing, 370 sandwich spread, 370 stick, 369 tub,369

content of trans acids, 368 preparation, 354

Marine oils composition of fatty acids

cod,373 herring, 373 menhaden oil, 373

positional distribution of fatty acids cod,219 harbor seal, 219 herring, 219 lobster, 219 mackerel,219 menhaden oil, 373 periwinkle, 219 sea whale, 219 skate, 219 squid, 219

Mass spectrometry alkylacylglycerols

major ions, 176 base peak, 40 chemical ionization, 108, 179 diacylglycerols

acetates, 172 t-butyldimethylsilyl ethers, 174-175 major ions, 172, 173 underivatized, 171-173

dual isotope, 110 electron impact, 158-179 fatty acids

acetylenic, 44 acylium ion, 40

lrukx

lrula

Mass spectrometry (COnl'd) fatty acids (cont'd)

anthracene, 43 benzyl esters, 44 branched,41 t-butyldimethylsilyl esters, 41 cyclic, 42 deuterated, 49, 107 epoxy, 45 location of unsaturation, 42-44 methyl esters, 40, 107 monoethylenic, 43 polyethylenic, 43 pyrrolidides, 42, 43 ring location, 42, 43 saturated, 40, 41 stable-isotope-Iabeled, 48, 49 trimethylsilyl esters, 41

field desorption, 179 field ionization, 108, 179 with gas-liquid chromatography, 158 general principles, 158 McLafferty rearrangement, 40 monoacylglycerols

major ions, 157-161 trimethylsilyl ethers, 162

monoalkenylglycerols major ions, 169, 170 trimethylsilyl ethers, 170

monoalkylglycerols dimethoxy derivatives, 164 isopropylidenes, 165 major ions, 163-167, 169 trimethylsilyl ethers, 167

triacylglycerols diisovaleroyl, 178 direct probe, 177, 178 estolides, 177, 178 hydrogenated, 178 long-chain, 177 short-chain, 178

Mayonnaise composition of fatty acids, 370 general composition, 355

Menhaden oil composition of fatty acids, 373 deacylation with pancreatic lipase, 201 gas-liquid chromatography, 154

Methods of derivation of lipids (see also Chemical synthesis)

acetonation, 127 acetylation, 127 alkylation,S, 346 benzylation, 5 bromination, 83, 106, 256 p-bromophenacylation, 5 butylation, 346, 348 t-butyldimethylsilylation, 128

Methods of derivation of lipids (conl'd) deuteration, 51, 83 epoxidation, 45, 52 hydrogenation, 127, 353 methoxylation, 129 methylation,S, 346, 347 naphthacylation, 5 p-phenylphenacylation, 5 trifluoroacetylation, 129 trimethylsilylation, 5, 128

Microbial lipids composition of fatty acids, 21 positional distribution of fatty acids in

triacylglycerols bacteria, 228, 229 yeasts, 228, 229

Microsomal lipids composition of fatty acids

brain, 427 chicken, 407 liver, 426 man, 401, 416, 427 myocardium, 416 ox,424 rabbit, 401 rat, 401, 426 skeletal muscle, 401

Milk lipids composition of fatty acids

cow, 372, 403 dog, 403 goat, 210, 403 guinea pig, 403 horse, 403 pig, 210, 212, 403 sheep, 403

positional distribution of fatty acids nonruminant milk fats, 210, 221 ruminant milk fats, 209-211

stereospecific analysis, 209-211, 221

Mitochondrial lipids composition of fatty acids

adrenals, 399 elephant, 399 ox, 424 pig, 399 rat, 399, 426

Molecular rotation 3-acyl-sn-glycerols, 275 1,2-diacetyl-3-acyl-sn-glycerols, 277 1,2-diacyl-3-myristoyl-sn-glycerol, 277 1,2-isopropylidene-3-acyl-sn-glycerols, 275

459

Monoacylglycerols (see also Chemical synthesis, Gas-liquid chromatography, Mass spec­trometry, Thin-layer chromatography)

acyltransferase nature of products, 304

460

Monoacylglycerols (cont'd) acyltransferase (cont'd)

stereospecificity, 302, 304 substrate specificity, 302, 303

kinase nature of products, 296 stereospecificity, 296 substrate specificity, 296

lipase occurrence, 328 substrate specificity, 328 transacylase, 304

triacylglycerol synthetase stereochemical course, 315 tissue distribution, 312

Monoalkenylglycerols, see Chemical synthesis, Gas-liquid chromatography, Mass spec­trometry, Thin-layer chromatography, Physical properties

Monoalkylglycerols, see Chemical synthesis, Gas­liquid chromatography, Mass spectrom­etry, Thin-layer chromatography

Monoethylenic fatty acids (see also Gas-liquid chromatography, Mass spectrometry, Thin-layer chromatography)

elaidic,25 erucic, 23 geometric isomers, 22 oleic, 23 positional isomers, 22 vaccenic, 23

Monoglycerides, see Monoacylglycerols Montanic (octacosanoic) acid

occurrence, 25 Myocardium lipids

composition of fatty acids man, 416 microsomes,416

Myristelaidic (trans-9-tetradecenoic) acid equivalent chain lengths of esters, 23

Myristic (tetradecanoic) acid I3C-Iabeled, 88 14C-Iabeled, 89 deuterated, 80 occurrence, 358, 359, 363, 364, 371-373 positional distribution in triacylglycerols,

209,210,212,213,215,217,222,225, 227,229

tritiated, 97 Myristoleic (cis-9-tetradecenoic) acid

equivalent chain length of esters, 23 occurrence, 371-373

Nervonic (l5-tetracosenoic) acid equivalent chain lengths of esters, 23 occurrence, 394, 411, 419, 422, 424, 432-

434

Neutral lipids composition of fatty acids

brain, 414 chicken, 388 cultured cells, 423 dog, 388 fetal, 414 frog, 388 guinea pig, 388 heart, 414 kidney, 414 liver, 414 lung, 414 man, 388, 423 maternal, 414 mouse, 388 rabbit, 388 rat, 388 sea lion, 388 sheep, 388

Nomenclature of lipids fatty acids, 1, 341, 342 stereospecific numbering, 235 triacylglycerols, 234

Nonadecanoic acid I3C-Iabeled, 88 I'C-Iabeled, 90 deuterated, 81 tritiated, 98

Nuclear magnetic resonance spectroscopy chemical shift of protons, 57, 1I5, 182 diacylglycerols, 279 fatty acids

conjugated, 182 I3C spectra, 57, 1I3 double-bond location, 114 group assignments, 57, 113

monoacylglycerols, 279 triacylglycerols

diisovaleroyl, 182 enantiomeric shift difference, 229, 278 high performance, 278 lanthanide shift, 181, 182 location of acetate, 181 long-chain, 181 positional isomers, 181-182 short-chain, 182 signal shift reagents, 278

Index

Nut lipids (see also separate entries for individual fats)

composition of fatty acids almond, 365 beechnut, 365 brazil, 365 cashew, 365 chestnut, 365 filbert, 365 macadamia, 365

Index

Nut lipids (cont'd) composition of fatty acids (cont'd)

pecan, 365 pilinut, 365 pine, 365 pistachio, 365 walnut, 365

Nutritional factors effect on lipid biosynthesis, 316

Octadecanoic acid, see Stearic acid I-Octadecanoyl-2-acetyl-rac-glycerol

equivalent chain length values, 135 RJvalues, 135

Octanoic acid, see Caprylic acid Oil processing

bleaching, 354 color reversion, 352 deodorization, 352 finishing, 352 hydrogenation, 353 imparting firmness, 354 interesterification, 353, 354 trans isomerization, 354, 368 nonselective hydrogenation, 353 solvent extraction, 352 winterization, 353

Oleic (cis-9-octadecenoic) acid 13C-Iabeled, 88, 114 14C_Iabeled, 89, 101 deuterated, Ill, 112 equivalent chain length of esters, 342, 343 infrared, 111, 112 isomers, 85, 98 occurrence, 358, 359, 363-367, 369-373 :.Jruclear magnetic resonance spectroscopy, 113 perdeuterated, 85, 112 positional distribution in triacylglycerols, 209,

215, 217-222, 225-227, 229 selective acylation of isomers, 308, 309 tritiated, 98

Olive oil composition of fatty acids, 359 positional distribution of fatty acids, 225 sources, 361

Optical rotation concentration dependence, 278 diacylglycerols, 58, 199 fatty acids, 58 monoacylglycerols, 58 triacylglycerols, 58, 198

Optical rotatory dispersion 1,2-diacetyl-3-myristoyl-sn-glycerol, 273 1,2-dimyristoyl-3-acetyl-sn-glycerol, 273 1,2-dipalmitoyl-sn-glycerol, 273 enantiomeric acylglycerols, 198, 273 1,2-isopropylidene-sn-glycerol, 273 3-palmitoyl-sn-glycerol, 273

Ovarian lipids composition of fatty acids

cow, 391 pig, 391

Ox tissue lipids composition of fatty acids

adipose tissue, 387, 392 bile, 467 cytoplasm, 424 erythrocytes, 394 heart, 424 lung, 388 microsomes, 424 milk,403 mitochondria, 424 nuclei,424 ovaries, 391 pancreas, 393 serum, 420 spermatozoa, 397 testes, 390 thymus, 395 thyroid, 392

positional distribution of fatty acids in triacylglycerols

adipose tissue, 217 milk fat, 209, 211

Oxidative cleavage location of double bonds, 126 ozonolysis, 51 permanganate-periodate oxidation, 127 potassium permanganate, 51 reductive ozonolysis, 126 sodium periodate, 51

Ozonolysis double bond location, 51 reductive ozonolysis, 126

Palmitelaidic (trans-9-hexadecenoic) acid equivalent chain lengths of esters, 23

Palmitic (hexadecanoic) acid 13C_Iabeled, 108, 109 14C-Iabeled, 101 occurrence, 363-367, 369-373 perdeuterated, 80 positional distribution in triacylglycerols,

209-215,217-222, 225-227, 229 tritiated, 97

Palmitoleic (cis-9-hexadecanoic) acid 13C_Iabeled, 88 14C-Iabeled, 89, 101 equivalent chain length ot' esters, 23 isomers of, 85, 89, 101 occurrence, 358, 359, 363-367, 370-373 perdeuterated, 85 positional distribution in triacylglycerols,

210, 212-215, 216-221, 225-227, 229

461

462

Palm kernel oil composition of fatty acids, 363

Palm oil composition of fatty acids, 363

2-Palmitoyl-3-oleoyl-sn-glycerol, 311 Pancreatic lipase

fatty acid specificity, 20 I positional specificity, 200, 271 procedure, 201, 202 stereospecific analysis of triacylglycerols, 201,

270 yield of diacylglycerols, 201

Pancreatic lipids composition of fatty acids

guinea pig, 393 man, 393 ox, 393 phospholipids, j93 steryl esters, 393 triacylglycerols, 393

formation of methyl esters, 393 Peanut oil

composition of fatty acids, 359 hydrogenated, 354 interesterified, 187, 226 positional distribution of fatty acids, 224, 226 sources, 357 triacylglycerol composition, 185, 186

Pecan nut oil composition of fatty acids, 365

Periwinkle oil positional distribution of fatty acids, 219

Petroselaidic (trans-6-octadecenoic) acid equivalent chain length of esters, 23

Petroselinic (cis-6-0ctadecenoic) acid equivalent chain length of esters, 23

Pharmacological factors effect on lipogenesis, 317-319

Pharyngeal lipase stereospecificity, 324

Phosphatidic acid biosynthesis, 293

acyltransferases, 292, 293 inhibition by monoacylglycerols, 315 kinases, 204, 296, 297

phosphohydrolases cytosolic, 305

hepatic, 306 intestinal, 305 mitochondrial, 306 rat, 306 relative activity, 306 substrate specificity, 305, 306

Phosphatidylcholine acetolysis, 125 composition of fatty acids

adipose tissue, 387

Phosphatidylcholine (cont'd) composition of fatty acids (cont'd)

bile, 407 calf, 395 chicken, 401 chylomicrons, 430 cytoplasm, 424 dog, 407, 433 epidermal cells, 398 feces, 433 fetal, 418 Golgi,426 heart, 424 hepatoma, 402 lipoproteins, 430 liver, 402, 426 lymphocytes, 395 man, 398, 407, 418 microsomes, 424, 426 mitochondria, 424, 426 mouse, 402 nuclear, 424 ox, 387, 407, 424 pig, 387, 395, 399, 407 plasma membranes, 402, 426 postnatal, 418 rabbit, 395,401 rat, 387, 399, 401, 402, 407, 426, 430 sarcotubular membranes, 401 sheep, 407 skeletal muscle, 401, 418 soy lecithin, 343

Index

dephosphorylation with phospholipase C, 124 Phosphatidylethanolamine

acetolysis, 125 composition of fatty acids

adipose tissue, 387 brain, 417, 427 calf, 395 chicken, 40 I Golgi,426 gray matter, 417, 427 liver, 426 lymphocytes, 395 man, 401, 417, 427 microsomes, 426 mitochondria, 426 myelin, 427 pig, 395 plasma membranes, 426 rabbit, 395, 401 rat, 401, 426 sarcoplasmic membranes, 401 skeletal muscle, 40 I synaptosomes, 427 variation with age, 417 white matter, 417, 427

dephosphorylation with phospholipase C, 124

Index

Phosphatidylphenols deacylation with phospholipase A2, 203 preparation, 203 stereospecific analysis of triacylglycerols,

203-207 thin-layer chromatography, 204

Phosphatidylserine acetolysis, 125 composition of fatty acids

chicken, 401 Golgi,426 liver, 426 man, 401 microsomes, 426 rabbit, 401 rat, 401, 426 sarcotubular membranes, 401 skeletal muscle, 40 I

dephosphorylation with phospholipase C, 124 Phospholipases

phospholipase A2 fatty acid specificity, 3, 203 positional specificity, 204, 260, 270, 271 procedure, 204 substrate specificity, 260, 270 stereospecific analysis of acylglycerols, 200,

270 phospholipase C

dephosphorylation of glycerophospho­lipids, 124

substrate specificity, 125, 260 Phospholipids

acetolysis, 125 composition of fatty acids

adenoma, 419 adipose tissue, 392 adrenals, 410, 411, 415, 419 boar, 397 bull, 397 chicken, 388 cow, 388 dog, 388 elephant, 399 epidermal cells, 398 fetal, 414 frog, 388 Graafian follicles, 391 guinea pig, 388, 393 heart, 408, 410, 415 kidney, 408 lipoproteins, 429 liver, 408, 410, 415 lung, 388 man, 388, 393, 398,419, 429 maternal, 414 mouse, 388, 390 ox, 390, 392, 393, 415 pig, 390, 391, 398

Phospholipids (com'd) composition of fatty acids (com'd)

plasma, 429 rabbit, 388, 392, 397 ram, 397 sea lion, 388 serum, 429 skeletal muscle, 408 spleen, 415 testes, 390, 415 thyroid, 392 turtle, 388 WI-38 cells, 423

463

WI-38VA 13A cells, 423 dephosphorylation with phospholipase C,

124 Piezoelectric effect

definition, 280 diacylglycerols, 280 enantiomers, 280 monoacylglycerols, 280 piezoelectricity, 280 piezoelectrometer, 280 racemates, 280 triacylglycerols, 280

Pig tissue lipids composition of fatty acids

adipose tissue fat, 387, 412, 413 adrenals, 412 bile, 407 blood,412 epidermal cells, 398 erythrocytes, 394 heart, 412 kidney, 412 liver, 386, 412 lymphocytes, 395 milk, 412 mitochondria, 399 ovaries, 391 testes, 390

positional distribution of fatty acids in triacylglycerols

adrenals, 218 blood, 212 heart, 218 inner back fat, 212 kidney, 218 liver, 212 milk, 210, 212 outer back fat, 218

Pilinut oil composition of fatty acids, 365

Pine nut oil composition of fatty acids, 365

Pistachio nut oil composition of fatty acids, 365

Plant oils, see Seed oils, Vegetable oils

464

Plasma lipids composition of fatty acids, 429 lipoproteins, 430 man, 429 positional distribution of fatty acids in triacyl­

glycerols, 222 Plasma membrane lipids

composition of fatty acids hepatoma, 402 liver, 402 mouse, 402 phosphatidylcholines, 402 rat, 402 triacylglycerols, 402

Polarimetry allenic acids, 272 diacylglycerols, 272 epoxy acids, 61 hydroxy acids, 60 methyl-branched acids, 58, 59 monoacylglycerols, 255, 256 triacylglycerols, 272

Polyethylenic acids equivalent chain length of esters, 28 resistance to pancreatic lipase, 3

Positional distribution of fatty acids (see also Stereospecific analysis and entries Jor indi­vidual Jats, animal tissues, and species)

diacylglycerols, 163 triacylglycerols

adipose tissue, 217 animal milk fats, 209, 210, 211 bacteria, 229 butteroil, 209 egg yolk, 220 human tissues, 221 intestine, 215 liver, 213, 214 marine oils, 219 pig tissues, 212, 218 plasma lipoproteins, 222 seed oils, 215, 226, 227 yeast, 229

Preparation of derivatives, see methods of derivation of lipids

Propionic (propanoic) acid occurrence, 13 relative retention time, 13, 15 steam distillation, 12

Protected seed oils effect on milk fat composition, 211

Protective groups benzyl, 247 benzylidene, 246 carbonate, 248 isopropylidene, 245 p-nitrobenzoyl, 248

Protective groups (cont'd) selection of, 244 tetrahydropyranyl, 248 2,2,2-trichloroethoxycarbonyl, 247 triphenylmethyl (trityl), 246

Purification of lipids DEAE cellulose, 131 fatty acid methyl esters, 4 free fatty acids, 7 removal of nonlipids

antioxidants, 131, 383 silica gel, 132 spray reagents, 7, 383

Sephadex G-25, 131 thin-layer chromatography, 132 total lipids, 382

Puromycin effect of fat absorption, 318 effect on lipid biosynthesis, 318

Pyrolysis deutero esters, 49 double bond location, 49 of ozonides, 51

Pyruvate kinase determination of glycerol, 130

Quantitative analysis diacylglycerols

absolute amounts, 139, 156 elution profiles, 140 gas-liquid chromatography, 156 recoveries, 156-158 response factors, 157

fatty acids absolute amounts, 347, 383, 384 elution profiles, 383 gas-liquid chromatography, 347, 348,

383,384 recoveries, 347, 383, 384, 436 response factors, 347

Index

use of internal standards, 139, 347, 384 glycerol, 130 sterols

as butyrates, 348, 349 triacylglycerols

absolute amounts, 139, 156 elution profiles, 140 gas-liquid chromatography, 156-158 recoveries, 156-158 response factors, 157 use of internal standards, 156

Rabbit tissue lipids composition of fatty acids

adipose tissue, 392, 415 adrenal, 415

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Rabbit tissue lipids (cont'd) composition of fatty acids (cont'd)

erythrocytes, 394 heart, 415 liver, 415 lung, 388 lymphocytes, 397 skeletal muscle, 401 spermatozoa, 397 spleen, 415 testes, 415 thymus, 395 thyroid, 392

positional distribution of fatty acids in triacyl­glycerols

adipose tissue, 217 liver, 213

Racemates, 263 Radioactive lipids

analysis of, 102-107 I'C-labeled, acylglycerols

biosynthesis, 99 chemical synthesis, 265, 266 fatty-acid-labeled, 265 glycerol-labeled, 266

I'C-labeled alkylacylglycerols biosynthesis, 301 chemical synthesis, 266, 267 fatty-acid-labeled, 267 glycerol-labeled, 266

I'C-labeled fatty acids biosynthesis, 99 chemical synthesis, 92 table of, 89, 90

3H-labeled acylglycerols biosynthesis, 10 I chemical synthesis, 265, 266 fatty-acid-labeled, 265 glycerol-labeled, 266

3H-labeled alkylacylglycerols biosynthesis, 303 chemical synthesis, 266, 267 fatty-acid-labeled, 267 glycerol-labeled, 267, 303

3H-labeled fatty acids biosynthesis, 99 chemical synthesis, 94-97 table of, 97, 98

Radiochemical purity determination, 105 3H/ I·C ratio, lOS

Radio-gas-liquid chromatography fatty acids

apparatus, 103 I·C detection, 104, 207

3H detection, 104 glycerol esters, 326

Raman spectroscopy cis I trans isomer content, 181 determination of unsaturation, 181

Random distribution of fatty acids diacylglycerols

I-random 2-random, 183 2-random 3-random, 183

triacylglycerols I-random 2-random 3-random, 183 1,2-random 3-random, 183 1,2,3-random, 183 1,3-random 2-random, 183

Rapeseed oil composition of fatty acids, 359 hydrogenated, 354

465

positional distribution of fatty acids, 224, 226 sources, 360

Rat tissue lipids composition of fatty acids

adipose tissue, 386, 387 adrenals, 399, 410, 411 bile, 407 chylomicrons, 405 crypt cells, 421 Ehrlich ascites, 422 feces, 435 Golgi,426 heart, 408, 410, 420 hepatoma, 402 kidney, 408 lipoproteins, 430 liver, 386, 402, 408, 410, 422 lung, 388 microsomes, 426 mitochondria, 426 plasma membranes, 426 skeletal muscle, 401, 408 skin, 434 testes, 390 villus cells, 421

positional distribution of fatty acids in triacyl-glycerols

adipose tissue, 217 intestinal mucosa, 215 liver, 213, 214

Reductive hydrogenolysis lithium aluminum hydride, 126 Vitride reagent, 125

Relative retention times (see also Gas-liquid chromatography)

diacylglycerols, 140, 152 fatty acids, 13, 15 monoacylglycerols, 147 steryl esters, 140 triacylglycerols, 140, ISS

Reversed-phase chromatography column, 139

466

Reversed-phase chromatography (com'd) detection of lipids, 139 resolution of lipids, 139 thin-layer, 139

Rf values (see also Thin-layer chromatography) definition, 132 effect of chain length, 135 effect of substitution, 135 table of, 134

Ricinelaidic (trans-9,12-hydroxy-octadecenoic) acid, 39

Ricinoleic (cis-9,12-hydroxy-octadecenoic) acid, 39

Safflower oil composition of fatty acids, 358 sources, 360

Salad dressing composition of fatty acids, 355

Salad oils composition of fatty acids,

commercial, 366 household, 366

Saponification recommended procedure, 2, 350, 351

Sarcotubular membrane lipids composition of fatty acids, 401

chicken, 40 I rabbit, 401 rat, 401

Sea lion lipids lung

composition of fatty acids, 388 Seed oils (see also Vegetable oils)

composition of fatty acids corn, 358 cottonseed, 358 estolides, 227 olive, 359 peanut, 226, 359 rapeseed, 226, 359 safflower, 358 Sapium sebiferum, 227 sesame, 359 soybean, 358

positional distribution of fatty acids cocoa butter, 225 coconut oil, 225 corn, 225 linseed, 225 Monnina emarginata, 227 olive, 225 peanut, 226 rapeseed, 226 Sapium sebiferum, 227 soybean, 226

Separation factors definition, 143 in gas-liquid chromatography, 145 in thin-layer chromatography, 133-139

Sesame oil composition of fatty acids, 359 sources, 361

Shea nut oil composition of fatty acids, 363

Sheep tissue lipids composition of fatty acids

bile, 407 fetal, 414 maternal, 414 milk fat, 403 spermatozoa, 397

Index

positional distribution of fatty acids in triacyl-glycerols

liver, 213 lymph,215 milk fat, 210

Shortenings composition of fatty acids

commercial, 367 household, 367

Skate oil positional distribution offatty acids, 219

Skeletal muscle lipids composition of fatty acids man, 418 rat, 408

Skin lipids composition of fatty acids

man, 432 rat, 434

Source of enantiomeric sn-glycerols D-mannitol, 235 L-mannitol, 235 quebrachitol, 237 D-serine, 238 L-serine, 238

Soybean oil composition of fatty acids, 358, 366 hydrogenated, 353 positional distribution of fatty acids, 225 sources, 356

Soy lecithin composition of fatty acids, 343

Specific rotation alkylalkenylglycerols, 240 diacylglycerols, 259, 261 dialkylglycerols, 240 1,2-isopropylidene-3-acyl-sn-glycerols, 251, 254 2,3-isopropylidene-I-acyl-sn-glycerols, 251 monoacylglycerols, 252-254 monoalkylglycerols, 240 triacylglycerols, 262, 264

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Spectrophotometry infrared,53 ultraviolet, 53

Spermatozoa lipids composition of fatty acids

boar, 397 bull,397 man, 397 phospholipids, 397 rabbit, 397 ram, 397

content of aldehydes, 397 Sphingomyelin

composition of fatty acids epidermal cells, 398 Ehrlich ascites, 422 liver, 422 man, 398 pig, 398 plasma membrane, 422 rat, 422

Spleen lipids composition of fatty acids

rabbit, 415 Squid oil

positional distribution offatty acids, 219 Stable-isotope-Iabeled fatty acids (see also

Deuterated fatty acids) biosynthesis, 85, 91 chemical synthesis, 78 table of, 80, 81

Stearic (octadecanoic) acid 13C-labeled, 88 I'C-labeled, 89, 101 deuterated, 80, 81 occurrence, 35~ 359, 363-36~ 369-373 positional distribution in triacylglycerols, 209-

215,217-222,225-227,229 tritiated, 97, 98

I-SteaFoyl-2-linoleoyl-sn-glycerol, 311 Stereospecific analysis (see also Positional distri­

bution of fatty acids, Triacylglycerols) accuracy, 205, 206 application

animal fats, 208-220 human tissue lipids, 220-224 marine oils, 219 microorganisms, 228 plant oils, 224 yeast, 228

calculations, 183 methods

chemical, 198, 264 enzymatic, 199, 200, 205 internal standards, 207 physical, 198 recommended procedure, 205

Stereospecific (sn) numbering rules, 123, 198

Sterols butyl esters, 348-350 gas-liquid chromatography, 140, 348-350 quantitation, 348, 349 Rj values, 134 standards, 348, 349

Steryl esters gas-liquid chromatography, 140 1V values, 134

Storage of radioactive lipids methods of preservation, 107 self-radio lysis, 107

Sunflower seed oil composition of fatty acids, 358, 366 sources, 360

Synthesis, see Chemical synthesis

Tariric (6-octadecynoic) acid mass spectrometry, 44

Testes composition of fatty acids

mouse, 390 ox,39o pig, 390 rabbit, 415 rat, 390

Tetradecanoic acid, see Myristic acid 1-Tetradecanoyl-2-hexanoyl-rac-glycerol

equivalent chain-length values, 135 1V values, 136

467

Thin-layer chromatography (see also AgN03 thin­layer chromatography, Arsenite thin­layer chromatography, Borate thin-layer chromatography, Reversed phase chroma­tography)

autoradiography, 105 charring, 133, 139 choice of adsorbent, 132 choice of solvent, 133, 134 quantitation, 139 recovery of lipid, 133 Rj values of neutral lipids, 134, 135

Thyroid lipids composition of fatty acids

OX, 392 rabbit, 392

Total fatty acids erythrocytes

cat, 394 dog, 394 guinea pig, 394 hamster, 394 man,394 mink, 394 monkey, 394

468

Total fatty acids (cont'd) erythrocytes (cont'd)

ox, 394 pig, 394 rabbit, 394

feces rat, 435

heart rat, 420

mucosal cells crypt, 421 rat, 421 villus, 421

skin surface man, 432 rat, 434

Triacetylglycerol gas-liquid chromatography, 129 mass spectrometry, 130 preparation, 129, 130

Triacylglycerols (see also Absolute configura­tion, AgN03 thin-layer chromatography, Biosynthesis, Chemical synthesis, Gas­liquid chromatography, Optical rotation, Piezoelectric effect, Positional distribu­tion of fatty acids, Stereospecific analysis, and entries under individual sources)

adenoma, 419 adipose tissue, 392, 412, 413, 415, 416 adrenals, 399, 411, 412, 415, 419 aorta, 416 blood, 412 chicken, 386 chylomicrons, 405, 430 circular dichroism, 198 cow, 391, 403 cytoplasmic, 424 dog, 403, 405, 413 elephant, 399 fecal, 433 fetal serum, 429 Graafian follicles, 391 guinea pig, 393, 403 heart, 408, 415, 416, 421 hepatic, 386, 408, 412, 415, 416 kidney, 408, 412 lipoproteins, 429, 430 man, 393,403,405; 416, 419, 429, 433 mass spectrometry, 176-179 melting points, 343 microsomal, 416, 424 milk, 403, 412 mitochondrial, 416, 424 mouse, 390 myocardium, 416 nomenclature, 198 nuclear, 424

Index

Triacylglycerols (cont'd) nuclear magnetic resonance spectroscopy, 199 optical rotatory dispersion, 198, 262 ovaries, 391 pancreas, 393 physical constants, 262-264 pig, 386, 390, 391, 399, 412, 413 rabbit, 392, 415 rat, 386, 390, 399, 405, 408, 411, 430 Rf values, 134 skeletal muscle, 408 spleen, 415 synthetase

activation, 312 intestinal, 312 purification, 312 rat, 312

synthetic, 262-264 testicular, 415 thyroid, 392

2,2,2-Trichloroethoxycarbonyl group introduction, 247 removal, 247

Triethylenic acids conjugated, 29 equivalent chain length of esters, 28

Trifluoroacetylation, 129 Trimethylsilylation,

acylglycerols, 128 alkylglycerols, 128 fatty acids, 5 procedure, 128

Triphenylmethyl (trityl) group introduction, 246 removal, 246, 268

Tritium labeled lipids, see Radioactive lipids Turtle tissue lipids

lung composition" of fatty acids, 388

UltraVIOlet spectroscopy band assignments, 56 determination of conjugation, 53, 56

Unsaturated fatty acids, see Acetylenic acids, Allenic acids, Diethylenic acids, Ethylenic acids, and Polyethylenic acids

Vaccenic (cis-11-octadecenoic) acid equivalent chain length of esters, 23

trans-Vaccenic (trans-11-octadecenoic) acid equivalent chain length of esters, 23

Vegetable oils composition of fatty acids, 356, 358, 359 content of atypical fatty acids, 224 positional distribution of fatty acids, 225-227 table of, 356

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(+)Vernolic (cis-I2,I3-epoxyoleic) acid enzymic hydration, 62, 63

Vitride reagent, I31

Walnut oil composition of fatty acids, 365

Wax esters Rf values, 134

Whale oil composition of fatty acids, 219 positional distribution of fatty acids, 219

Wheat flour fat positional distribution of fatty acids, 225

Wittig reaction, 83, 93

X-ray diffraction determination of acylglycerol structure

enantiomers, 279 polymorphs, 279 racemates, 279

Yeast triacylglycerols

469

positional distribution of fatty acids, 228, 229