Index

Page references in bold type refer to primary articles. References followed by t refer to material in tables.

Accelerated stability tests, 450t Aldehydes Aceituno oil, 233 from hydroperoxide decomposition, 389–390, Acetate-malonate pathway, 213–214 391t, 392t Acetic acid Alkoxy radical, 434 odorant in Irish sour cream butter, Alkylbenzenes, 548–549 397t Alkyl radical, 434 Acetyl-CoA carboxylase, 214 All beef packer tallow 2-Acetyl-3-ethylpyrazine specifications of commercial grades, 177t in , 398t Almond oil, 233 2-Acetyl-3-methylpyrazine Amaranthus oil, 233 in cocoa butter, 398t Amides 2-Acetyl-5-methylthiazole production from fatty acids, 28 in cocoa butter, 399t Amines 2-Acetyloxazole production from fatty acids, 28 in cocoa butter, 399t 2-Amino-1-methyl-6-(5- Acetylpyrazine hydroxy)phenylimidazo[4,5-b]pyridine in sesame oils, 407t (5-OH-PhIP), 537 Acidolysis, 12, 187 2-Amino-1-methyl-6-phenylimidazo Acrid flavor, 420t [4,5-b]pyridine (PhIP), 537 Active oxygen method, 450–451 2-Amino-9H-pyrido-[2,3-b]indole (PhIP), 538 Acylglycerols. See also Triacylglycerols Anhydrous milkfat compositon and structure, 6–9 fatty acid composition, 124t Adulteration linear regression coefficients for physical of animal fats, 173 properties, 155t quality assurance against, 567, 574 lipid composition, 123–125, 124t Alcohols mechanical properties, 122–123 from hydroperoxide decomposition, 393 mechanical properties at large deformation, Alcoholysis, 12, 187 153–154

Bailey’s Industrial Oil and Fat Products, Sixth Edition, Six Volume Set. Edited by Fereidoon Shahidi. Copyright # 2005 John Wiley & Sons, Inc.

607 608 INDEX

Anhydrous milkfat (Continued) in animal fats, 194–195 mechanical properties at small deformation, classification, 436–445 148–152 commonly used in foods, 441t, 455–474 microstructure, 135–148 estimation and analysis in foods, 474 nucleation and crystal growth, 126–131, evaluation methods, 445–455, 448–449t, 450t 146–148 mechanism, 434–436 particle-counting fractal dimension, box- multiphase systems, 451–452 counting fractal dimension, and mean potential hazards from approved, 547–550 microstructural element, 146t and quality assurance of fats and oils, 574 polymorphism, 131–134 regulatory status, 475–476, 477–482t, processing conditions, 125, 157–158 491–509 rheologically determined fractal dimensions safety, 476–483 and pre-exponential terms, 138t science, technology, and applications, thermal and structural behavior compared to 431–483 cream, 110t scope of use in food, 433–434 Animal depot lipids, 161–171 synergism, 443–445 Animal fat-based frying fats, 195–197, 196t technological considerations in using, Animal fat-based shortenings, 195–197, 196t 474–475 Animal fats, 161–205 Antioxidants: regulatory status, 491–509 acylglycerol components, 162–168, 163t, 166t Antioxidants: science, technology, and acylglycerol structure-function relationship, applications, 431–483 168–171 Appearance, of fats and oils, 571–572 antioxidants in, 194–195 Appetize, 168 and bovine spongiform encepthalopathy (BSE), Apricot oil, 234 197–200 Arachidic acid and conjugated linoleic acids (CLAs), 203–205 composition in selected animal fats, greases, fatty acid source, 3t and vegetable oils, 163t as fuels, 200–202 hydrogen abstraction rate constants (by t-BuO), most important commercial, 161–162 314t patterns and trends in production and use, scission products from room temperature 179–182 oxidation, 324t quality indicators for edible, 171–174 volatile aldehydes from autoxidation, 391t recent developments, 197–205 Arachidonic oil, 520 regulatory and commercial classifications, ARASCO, 520 174–179, 175t, 176t, 177t, 178t Ascorbic acid specifications of commercial grades, 177t acceptable daily intake (ADI), 483t, 509t and trans-fatty acids, 202–203 antioxidant commonly used in food, 460–461 worldwide production, 180t conventionally permitted in foods, 508t Animal greases, 162, 182 effect on oxidation of soybean oil, 458t naming conventions for inedible, 178t regulations governing use, 477t prices at randomly chosen times in period regulatory status, 505–506 2000–2003, 180t secondary antioxidant, 442t prices between 2000–2003, 181t D-Ascorbic acid, See Erythorbic acid specifications of commercial grades, 177t Ascorbic stearate trading grades for technical, 177t regulations governing use, 477t worldwide production, 180t Ascorbyl acid Animal oils effect on oxidation of soybean oil, 458t as fuels, 200–202 Ascorbyl palmitate p-Ansidine value, 368–369, 573 acceptable daily intake (ADI), 509t Anthrocyanidin, 471 antioxidant commonly used in foods, 460–463 Anthrocyanin, 471 conventionally permitted in foods, 508t Antioxidants, 19–20 effect on oxidation of soybean oil, 458t INDEX 609

regulations governing use, 477t Borage oil, 234 regulatory status, 498, 501–503 fatty acid composition, 234t secondary antioxidant, 442t Borneo tallow, 235, 237 Ascorbyl stearate Bovine spongiform encepthalopathy (BSE), acceptable daily intake (ADI), 509t 197–200 antioxidant commonly used in foods, Brown grease, 162 461–463 specifications of commercial grades, 177t conventionally permitted in foods, 508t Buffalo gourd oil, 235 Astaxanthin, 506 Burnt flavor, 420t Atherosclerosis n-Butanal role of dietary fat, 589–600 in Gulf menhaden oil, 406t Autooxidation, 432–433 Butanoic acid and antioxidant mechanisms, 434–436 odorant in Irish sour cream butter, 397t fatty acids, 16–17 2-Butenal lipid free radical, 387–388 volatile compound in vegetable oils, 395t Á5-Avenasterol, 473 cis-2-Butenal Avocado oil, 234 in Gulf menhaden oil, 406t Avrami analysis, 66–67 Butter fatty acid composition, 4t , 234 fatty acid source, 3t Barbecuing flavor compounds, 396t, 396–397, 397t toxic substances produced by, 545–547 saponification equivalent, saponification value, Barley , and unsaponifiable matter, 10t plant sterol source, 523t Buttery flavor, 377t, 420t Beany flavor, 377t, 420t Butylated hydroxyanisole (BHA), 20, 440 Beef fat acceptable daily intake (ADI), 483t, 509t influence of diet on fatty acid composition, 166t in animal fats, 195 positional distribution of fatty acids in, 169t antioxidant commonly used in foods, 441t, Beef tallow, 161–162 457–458 fatty acid composition, 163t conventionally permitted in foods, 508t Behenic acid effect on oxidation of soybean oil, 458t composition in selected animal fats, greases, maximum level permitted, 501t and vegetable oils, 163t physical properties, 456t Benzaldehyde potential hazards, 547–548 in Gulf menhaden oil, 406t properties, applications, and regulations, 495t Benzoic acids, 467–468 regulations governing use, 477–478t Betapol, 250 regulatory approval status in different countries, BHA, See Butylated hydroxyanisole 502–503t BHT, See Butylated hydroxytoluene regulatory responsibilities, 502t Bile salts, 522 regulatory status, 493–497 Biodiesel, 12, 200–201 Butylated hydroxytoluene (BHT), 20, 440 Bis(2-ethylhexyl)phthalate acceptable daily intake (ADI), 483t, 509t hazards of, 549–550 in animal fats, 195 Blackcurrant oil, 234 antioxidant commonly used in foods, 441t, fatty acid composition, 234t 458–459 Bland flavor, 420t conventionally permitted in foods, 508t Bleachable fancy tallow, 178t effect on oxidation of soybean oil, 458t specifications of commercial grades, 177t maximum level permitted, 501t Bleaching physical properties, 456t animal fats, 184 potential hazards, 547–548 Blending, 244–245 properties, applications, and regulations, Bond dissociation energy 496t lipids, 281t regulations governing use, 479t 610 INDEX

Butylated hydroxytoluene (BHT) (Continued) composition in selected animal fats, greases, regulatory approval status in different countries, and vegetable oils, 163t 502–503t formula, 3t regulatory responsibilities, 502t Caproic acid regulatory status, 493–497 formula, 3t 2-Butyl-3,6-dimethylpyrazine Caprylic acid in cocoa butter, 398t formula, 3t 2-Butyl-4-ethyl-5-methyloxazole Caraway oil, 235 in cocoa butter, 399t Carbohydrate-based surfactants tert-Butylhydroquinone (TBHQ), 440 from fatty acids, 30 acceptable daily intake (ADI), 483t, 509t Carbonyl compounds in animal fats, 195 from lipid oxidation, 369–370 antioxidant commonly used in foods, 441t, and quality assurance of fats and oils, 573 459 Cardboard flavor, 420t conventionally permitted in foods, 508t Cardiovascular disease effect on oxidation of soybean oil, 458t role of dietary fat, 589–600 maximum level permitted, 501t Carnosic acid, 20, 469–470 physical properties, 456t Carnosine, 469–470 properties, applications, and regulations, 499t Carnosol, 469 regulations governing use, 482t a-Carotene, 506, 507 regulatory approval status in different countries, b-Carotene, 507 502–503t antioxidant commonly used in food, 463–464 regulatory responsibilities, 502t regulatory status, 506 regulatory status, 497–498 secondary antioxidant, 442t 2-Butyl-4-methyl-5-ethyloxazole Carotenoids, 443 in cocoa butter, 399t antioxidants commonly used in foods, 441t, Butyloxyl radicals 463–464 alkene structure effect, 317t and quality assurance of fats and oils, 571, Butyric acid 572 common name and formula, 3t regulatory status, 506–508 secondary antioxidant, 442t Calcium ascorbate, 505 in vegetable oils, 218 Calendic acid Carrot, 235 in vegetable oils, 221t Cashew oil, 235 Calendula oil, 222t, 235, 253 Castor oil, 222t, 224–225 Camelina oil, 235 fatty acid composition, 4t Campesterol, 524 saponification equivalent, saponification value, Campesteryl fernlate, 473 iodine value, and unsaponifiable matter, Cancer 10t and trans-fatty acids, 536 Catalase, 443 , 235 Catalysts Canola oil, 222t for lipid oxidation initiation, 273–280 fatty acid composition of anhydrous milkfat Catalytic partial hydrogenation, 25–26 solutions, 124t Cattle fats, 161, 162 flavor compounds, 402–403 Cereals influence of diet on fatty acid composition of antioxidants from, 467–474 pork and beef fat, 166t plant sterol sources, 523t lipid composition of anhydrous milkfat diluted Charbroiling with, 124t toxic substances produced by, 545–547 volatile compounds in, 395t Chelating agents, 442–443 Canthaxanthin, 506 Chemistry of fatty acids, 1–38 Caprenin, 532 Cherry oil, 235 Capric acid Chia oil, 235 INDEX 611

Chicken fat Conjugated acid oils, 224 fatty acid composition, 163t Conjugated dienes, 364–365 positional distribution of fatty acids in, 169t Conjugated , 536 Chicken fats, 161 biological function, 580–581 Chinese vegetable tallow, 235–236 food fortification with, 581 Chlorophylls Conjugated trienes, 364–365 and quality assurance of fats and oils, 571, 572 Copper Choice white grease, 175, 178t as catalyst for fatty acid hydrogenation, 26 specifications of commercial grades, 177t as catalyst for hydroperoxide decomposition, Cholesterol, 521–522, 542t 442 in animal fats, 168 catalyst for lipid oxidation initiation, 273–277 and atherosclerosis, 592–593, 596–597 Coriander oil, 236 and coronary heart disease, 243 Corn oil, 226 Cholesterol oxidation products, 541–543 fatty acid composition, 4t, 221t Chylomicrons, 583 fatty acid source, 3t Cinnamic acids, 467–468 genetically modified, 257 Citric acid, 442 influence of diet on fatty acid composition of acceptable daily intake (ADI), 509t pork and beef fat, 166t conventionally permitted in foods, 508t plant sterol source, 523t effect on oxidation of soybean oil, 458t saponification equivalent, saponification regulations governing use, 480t value, iodine value, and unsaponifiable secondary antioxidant, 442t matter, 10t Cobalt solubility of synthetic antioxidants in, 456t catalyst for lipid oxidation initiation, 273–277 volatile compounds in, 395t Cocoa butter, 222t, 225–226 worldwide production, 180t fatty acid composition, 221t Corny flavor, 421t fatty acid source, 3t Coronary heart disease, 243 flavor compounds, 397–399, 398t, 399t and trans-fatty acids, 536 interesterification, 191 Cottonseed oil, 222t, 226–227 oxazoles and thiazoles in, 399t adulteration quality assurance, 574 polymorphic forms and their melting fatty acid composition, 4t, 221t temperatures, 51t fatty acid source, 3t polymorphism, 110–113 influence of diet on fatty acid composition of pyrazines in, 398t pork and beef fat, 166t triacylglycerol composition, 8t saponification equivalent, saponification oil, 222, 222t, 226 value, iodine value, and unsaponifiable fatty acid composition, 4t matter, 10t fatty acid source, 3t volatile compounds in, 395t saponification equivalent, saponification value, worldwide production, 180t iodine value, and unsaponifiable matter, 10t Coumesterol, 533–534 triacylglycerol composition, 8t Crambe oil, 222t, 236 typical fatty acid composition, 221t C-reactive protein, 597 worldwide production, 180t Creutzfeldt-Jacob (CJ) disease, 197, 198, 200 Cod liver oil b-Cryptoxanthin, 506 fatty acid composition, 4t Crystal growth, 64–65 saponification equivalent, saponification anhydrous milkfat, 126–131, 146–148 value, iodine value, and unsaponifiable Crystalline microstructure, 68 matter, 10t Crystallization of fats and oils, 45–73 Color controlling, 68–73 edible fats, 171–172 fat crystal networks (anhydrous milkfat), of fats and oils, 571–572 126–127 Conjugable oxidation products (COP) assay, kinetics, 60–64, 65–67 364, 366 lipid phase behavior, 46–56 612 INDEX

Crystal networks, fat, See Fat crystal networks Density Cumyloxyl radicals and quality assurance of fats and oils, 571 solvent effects on rate of abstraction and Deodorization B-scission, 222t animal fats, 186–187 Cuphea oil, 236, 252 DHA, See Docosahexaenoic acid Cutting-floor fats, 162 Diacetyl Cycloarteryl ferulate, 473 odorant in Irish sour cream butter, 397t Cyclooxygenases (COX), 582–583 Diacid triacylglycerols, 78 role of n-3 PUFAs in regulating, Diacylglycerols, 9 588–589 crystallization, 46, 47 Cyclopropenoid fatty acids, 532 production from interesterification, 250 quality assurance of fats and oils, 568–569 Dairy fats 1,3-Dibehenoyl-2-oleoyl-sn-glycerol (BOB) fatty acid source, 3t occurrence in TAGs, 100t 2,4-Decadienal 2,5-Dibutyl-4-methyloxazole from autooxidation of unsaturated fatty acids, in cocoa butter, 399t 390, 391t 4,5-Dibutyloxazole in Gulf menhaden oil, 406t in cocoa butter, 399t from isomerization of linoleic acid, 313t 1,3-Dicaproyl-2-lauroyl-sn-glycerol (CLC) in lard, 400t occurrence in TAGs, 100t sensory characteristics, 392t Dietary fat and health, 577–600 trans,cis-2,4-Decadienal biochemistry of polyunsaturated fatty acids, volatile compound in vegetable oils, 395t 582–583 trans,trans-2,4-Decadienal chronic disease, 586–589 odorant in Irish sour cream butter, 397t food fortification, 581–582 in sesame oils, 407t molecular actions, 583–586 in stored soybean oil, 401t role in cardiovascular disease and volatile compound in vegetable oils, 395t atherosclerosis, 589–600 d-Decalactone Dietary reference intakes (DRIs) odorant in Irish sour cream butter, 397t fats, 578 Decanal 2,3-Diethyl-5-methylpyrazine from autooxidation of unsaturated fatty acids, in sesame oils, 407t 391t 2,5-Diethyl-3-methylpyrazine sensory characteristics, 392t in cocoa butter, 398t n-Decanal 2,6-Diethyl-3-methylpyrazine in Gulf menhaden oil, 406t in cocoa butter, 398t Decatrienal Differential scanning calorimetry in Gulf menhaden oil, 406t for lipid oxidation measurement, 374–375 2,4,7-Decatrienal Diglycerides, See Diacylglycerols from autooxidation of unsaturated fatty acids, 6,7-Dihydro-5H-cyclopentapyrazine 391t in cocoa butter, 398t 2-Decenal Dimer acids from autooxidation of unsaturated fatty acids, from fatty acids, 30–31 391t 2,5-Dimethyl-4-butyloxazole sensory characteristics, 392t in cocoa butter, 399t cis-4-Decenal 2,3-Dimethyl-5-butylpyrazine in Gulf menhaden oil, 406t in cocoa butter, 398t trans-2-Decenal 2,3-Dimethyl-5-ethylpyrazine volatile compound in vegetable oils, 395t in cocoa butter, 398t trans-4-Decenal 2,5-Dimethyl-3-ethylpyrazine in Gulf menhaden oil, 406t in cocoa butter, 398t Decenol 2,5-Dimethyl-5-isobutylpyrazine volatile compound in vegetable oils, 395t in cocoa butter, 398t INDEX 613

4,5-Dimethyloxazole 3,6-Dodecadienal in cocoa butter, 399t from autooxidation of unsaturated fatty acids, 2,3-Dimethylpyrazine 391t in cocoa butter, 398t 3,6,9-Dodecatrienal 2,5-Dimethylpyrazine from autooxidation of unsaturated fatty acids, in cocoa butter, 398t 391t 2,6-Dimethylpyrazine cis-6-Dodeceno-g-lactone in cocoa butter, 398t odorant in Irish sour cream butter, 397t Dimorphotheca oil, 236 Dodecyl gallate, 440 1,3-Dioleoyl-2-palmitoyl-sn-glycerol (OPO) antioxidant commonly used in foods, 459 in mixtures, 104–108 physical properties, 456t 1,3-Dioleoyl-2-stearoyl-sn-glycerol (OSO), regulatory status, 497–498 98–99 Dry fractionation, 192, 245–246 in mixtures, 104–108 occurrence in TAGs, 100t Edible animal fats 1,2-Dipalmitoyl-3-decanoyl-sn-glycerol (PP10) quality indicators for, 171–174 occurrence in TAGs, 100t Edible tallow, 174, 181, 182 1,3-Dipalmitoyl-2-elaidoyl-sn-glycerol (PEP), Codex Alimentarius standards, 175t, 176t 99 prices at randomly chosen times in period 1,2-Dipalmitoyl-3-myristoyl-sn-glycerol (PP14) 2000–2003, 180t occurrence in TAGs, 100t prices between 2000–2003, 181t 1,3-Dipalmitoyl-2-oleoyl-sn-glycerol (POP) specifications of commercial grades, 177t in mixtures, 104–108 Edible vegetable oils occurrence in TAGs, 100t worldwide production, 180t a,a-Diphenyl-b-picrylhydrazyl radical, 453, 454 Eicosadienoic acid Directed interesterification, 188–189 composition in selected animal fats, greases, 1,3-Disaturated-2-unsaturated mixed acid and vegetable oils, 163t triacylglycerols, 94–98 Eicosanoids, 578 1,3-Distearoyl-2-elaidoyl-sn-glycerol (SES), 99 Eicosapentaenic acid (EPA) 1,3-Distearoyl-2-linoleoyl-sn-glycerol (SLS), autooxidation in micelles, 17 96–98 discrimination against in lipase reactions, 15 occurrence in TAGs, 100t essential fatty acid, 578, 579–580 thermal properties of polymorphs, 96t food fortification with, 581 1,3-Distearoyl-2-oleoyl-sn-glycerol (SOS), formula, 3t 94–98 mode of action against chronic disease, in mixtures, 104–108 588–589 occurrence in TAGs, 100t as n-3 PUFA, 579–580 thermal properties of polymorphs, 96t volatile aldehydes from autoxidation, 1,3-Distearoyl-2-ricinoleoyl-sn-glycerol (SRS), 391t 96–98 Elaidic acid thermal properties of polymorphs, 96t ball and stick model, 6 1,3-Distearoyl-2-rycinoleoyl-sn-glycerol (SRS) 2-Elaidoyl glycerol (OEO), 98–99 occurrence in TAGs, 100t Eleostearic acid 1,3-Diunsaturated-2-unsaturated mixed acid in vegetable oils, 221t triacylglycerols, 98–99 EPA, See Eicosapentaenic acid Docosahexaenoic acid (DHA) Epoxidation autooxidation in micelles, 17 fatty acids, 21–22 discrimination against in lipase reactions, 15 Epoxy acid oils, 224 essential fatty acid, 578, 579–580 trans-4,5-Epoxy-trans-2-decenal food fortification with, 581 odorant in Irish sour cream butter, 397t formula, 3t in stored soybean oil, 401t, 402t mode of action against chronic disease, 589 trans-4,5-Epoxy-trans-2-nonenal as n-3 PUFA, 579–580 in stored soybean oil, 401t, 402t 614 INDEX

Erucic acid, 253 mechanical properties at small deformation, adverse effects, 530–531 148–152 composition in selected animal fats, greases, microstructure, 135–148 and vegetable oils, 163t nucleation and crystal growth, 126–131, formula, 3t 146–148 in vegetable oils, 221t polymorphism, 131–134 Erucic acid oils, 223 processing conditions, 125, 157–158 Erythorbic acid, 460 Fat mixtures conventionally permitted in foods, 508t polymorphism, 100–108 regulatory status, 498, 501–503 Fat product, feed grade, 174–175 secondary antioxidant, 442t Fats. See also Animal fats; Fatty acids Essential fatty acids, 577–578 adverse effects, 515–530 Ester exchange reactions adverse effects of natural constituents of, fatty acids, 12–13 530–533 Esterification. See also Interesterification adverse products from overheated, 543–545 fatty acids, 11–12 characteristics, 571 Estolides chemical reactions in, 535–537 from fatty acids, 30, 31–32 composition, 568–569 Ethane crystallization of, 45–73 volatile compound in vegetable oils, 395t dietary fat and health, 577–600 6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, fatty acids in commodity, 3t 440 flavor components, 387–408 Ethoxylation manufacturing hazards in processing, 550–552 fatty acids, 29 oxidation and antioxidant mechanisms, Ethoxyquin, 440, 503 434–436 acceptable daily intake (ADI), 509t polymorphism in, 77–116 antioxidant commonly used in foods, 441t, quality assurance of, 565–574 459 quality parameters, 568t conventionally permitted in foods, 508t toxicity and safety, 513–552 2-Ethyl-3,5-dimethylpyrazine toxic substances produced during smoking, in sesame oils, 407t charbroiling, and barbecuing, 545–547 Ethylenediaminetraacetic acid (EDTA), 442 volatile compounds in commercial, 395t, acceptable daily intake (ADI), 509t 395–408 conventionally permitted in foods, 508t worldwide production, 180t secondary antioxidant, 442t Fat-soluble vitamins, 527–530 2-Ethyl-5-methylpyrazine Fatty acid 4:0 in sesame oils, 407t common name and formula, 3t 2-Ethyl-3,5,6-trimethylpyrazine composition of anhydrous milkfat, 124t in cocoa butter, 398t occurrence, 3t Eutectic mixtures, 84 Fatty acid 6:0 Evening primrose oil, 236, 518–519 common name and formula, 3t fatty acid composition, 234t composition of anhydrous milkfat, 124t Extra fancy tallow occurrence, 3t specifications of commercial grades, 177t Fatty acid 8:0 common name and formula, 3t False flax, 236, 253 composition of anhydrous milkfat, 124t Fancy tallow occurrence, 3t specifications of commercial grades, 177t in vegetable oils, 221t Fat crystal networks, 121–158 Fatty acid 10:0 lipid composition, 123–125, 124t common name and formula, 3t mechanical properties, 122–123 composition in selected animal fats, greases, mechanical properties at large deformation, and vegetable oils, 163t 153–154 composition of anhydrous milkfat, 124t INDEX 615

occurrence, 3t composition of anhydrous milkfat, 124t in vegetable oils, 221t melting point, 5t Fatty acid 12:0 Fatty acid 17:1 common name and formula, 3t composition of anhydrous milkfat, 124t composition in selected animal fats, greases, Fatty acid 18:0 and vegetable oils, 163t common name and formula, 3t composition of anhydrous milkfat, 124t composition in selected animal fats, greases, occurrence, 3t and vegetable oils, 163t in vegetable oils, 221t composition of anhydrous milkfat, Fatty acid 14:0 124t common name and formula, 3t effect of diet on composition of pork and composition in selected animal fats, greases, beef fat, 166t and vegetable oils, 163t in g-linolenic acid oils, 234t composition of anhydrous milkfat, 124t melting point, 5t effect of diet on composition of pork and beef occurrence, 3t fat, 166t positional distribution in animal depot fats, occurrence, 3t 169t positional distribution in animal depot fats, in vegetable oils, 221t 169t Fatty acid 18:1 in vegetable oils, 221t composition in selected animal fats, greases, Fatty acid 14:1 and vegetable oils, 163t composition in selected animal fats, greases, composition of anhydrous milkfat, 124t and vegetable oils, 163t effect of diet on composition of pork and beef composition of anhydrous milkfat, 124t fat, 166t Fatty acid 15:0 in g-linolenic acid oils, 234t composition of anhydrous milkfat, 124t in linseed and linola oils, 227t Fatty acid 15:1 in , 228t composition of anhydrous milkfat, 124t percentage in major commodity oils, Fatty acid Fatty acid 16:0 18:2, Fatty acid 18:3, 4t common name and formula, 3t positional distribution in animal depot fats, composition in selected animal fats, greases, 169t and vegetable oils, 163t in tall oil, 232t composition of anhydrous milkfat, 124t in vegetable oils, 221t effect of diet on composition of pork Fatty acid 18:1 9c and beef fat, 166t common name and formula, 3t in g-linolenic acid oils, 234t melting point, 5t melting point, 5t occurrence, 3t occurrence, 3t Fatty acid 18:1 9t in palm oil, 228t melting point, 5t percentage in major commodity oils, 4t Fatty acid 18:2 positional distribution in animal depot fats, 169t composition in selected animal fats, greases, in vegetable oils, 221t and vegetable oils, 163t Fatty acid 16:1 composition of anhydrous milkfat, 124t composition in selected animal fats, greases, effect of diet on composition of pork and beef and vegetable oils, 163t fat, 166t composition of anhydrous milkfat, 124t in g-linolenic acid oils, 234t effect of diet on composition of pork and in linseed and linola oils, 227t beef fat, 166t in palm oil, 228t positional distribution in animal depot fats, percentage in major commodity oils, 4t 169t positional distribution in animal depot fats, Fatty acid 17:0 169t composition in selected animal fats, greases, in tall oil, 232t and vegetable oils, 163t in vegetable oils, 221t 616 INDEX

Fatty acid 18:2 9c12c Fatty acid 22:6 common name and formula, 3t effect of diet on composition of pork and beef melting point, 5t fat, 166t occurrence, 3t Fatty acid 22:6 4c7c10c13c16c19c Fatty acid 18:2 9t12t common name and formula, 3t melting point, 5t occurrence, 3t Fatty acid 18:3 Fatty acid 24:0 composition in selected animal fats, greases, composition in selected animal fats, greases, and vegetable oils, 163t and vegetable oils, 163t composition of anhydrous milkfat, 124t Fatty acid 24:1 effect of diet on composition of pork and beef composition in selected animal fats, greases, fat, 166t and vegetable oils, 163t in linseed and linola oils, 227t Fatty acid g-18:3 in palm oil, 228t in g-linolenic acid oils, 234t percentage in major commodity oils, 4t Fatty acids positional distribution in animal depot fats, 169t in animal fats, 164–168 in vegetable oils, 221t and atherosclerosis, 596 Fatty acid 18:3 9c12c15c biosynthesis, 213–217 common name and formula, 3t bulk properties, 9 occurrence, 3t chain shortening and extension, 33–34 Fatty acid 19:0 chemistry of, 1–38 melting point, 5t in commodity fats and oils, 3t Fatty acid 20:0 common in vegetable oils, 221t composition in selected animal fats, greases, composition and structure, 2–6 and vegetable oils, 163t composition of anhydrous milkfat, 124t composition of anhydrous milkfat, 124t composition of major commodity oils, 4t melting point, 5t conjugation, 32–33 Fatty acid 20:1 crystallization, 47 composition in selected animal fats, greases, epoxidation, 21–22 and vegetable oils, 163t ester exchange reactions, 12–13 Fatty acid 20:1 13c esterification, 11–12 occurrence, 3t ethoxylation, 29 Fatty acid 20:2 free radical addition reactions, 38–39 composition in selected animal fats, greases, Friedel Crafts acylation, 37–38 and vegetable oils, 163t hydrogenation, 25–27 Fatty acid 20:4 hydrolysis, 11 composition in selected animal fats, greases, hydroperoxide positional distributions in and vegetable oils, 163t oxidizing, 300t effect of diet on composition of pork and beef hydroxylation, 22–23 fat, 166t isomerization, 32 Fatty acid 20:5 5c8c11c14c17c lipase catalyzed reactions, 13–16 common name and formula, 3t melting points showing effect of chain length occurrence, 3t and unsaturation, 5t Fatty acid 22:0 nomenclature, 2–3, 3t composition in selected animal fats, greases, novel chemistry for functionalizing alkyl chain, and vegetable oils, 163t 36–39 composition of anhydrous milkfat, 124t olefin metathesis, 34–36 Fatty acid 22:1 oxidation, 16–25 composition in selected animal fats, greases, oxidative cleavage, 23–25 and vegetable oils, 163t quality assurance of fats and oils, 569 in vegetable oils, 221t reduction, 25–27 Fatty acid 22:1 13c structure modification, 32–36 common name and formula, 3t sulfation, 29 INDEX 617

a-sulfonates, 29–30 animal fat-based, 195–197, 196t surface active compounds and oleochemicals, measurement of deterioration, 377–378 27–32 Frying oils cis-Fatty acids, 3, 5 sensory evaluation, 426 trans-Fatty acids, 3, 5 Fuels in animal fats, 164, 202–203 animal fats and oils as, 200–202 and cancer, 536 Furan and coronary heart disease, 536 from hydroperoxide decomposition, 393 and neonatal growth, 537 2-Furfurylthiol Fatty acid salts, 5 in sesame oils, 407t Fatty acid synthase, 215 Fatty alcohols, 27 Gadoleic acid Fisher-Turnbull analysis, 67 composition in selected animal fats, greases, Fish fats and vegetable oils, 163t fatty acid source, 3t Gallates, 440. See also Dodecyl gallate; Octyl Fish oils gallate; Propyl gallate fatty acid composition, 4t antioxidants commonly used in foods, 459 flavor compounds, 404–407, 406t regulatory approval status in different countries, saponification equivalent, saponification value, 502–503t iodine value, and unsaponifiable matter, 10t regulatory responsibilities, 502t Fishy flavor, 377t, 421t regulatory status, 497–498 Flavan-3-ols, 471 Gas chromatography-olfactometry (GC-O), 427 Flavanonol, 471 Genetically modified seed oils, 255–257 Flavone, 471 Genistein, 533–534 Flavonoids GLA, See g-Linolenic acid antioxidant commonly used in foods, 441t Glucose oxidase, 443 from green tea, 467, 470–474 Glutathione peroxidase, 443 Flavonol, 471 Glycerol, 1, 216 Flavonone, 471 solubility of synthetic antioxidants in, 456t Flavor and sensory aspects, 413–427 triacylglycerol formation, 6–9 Flavor components of fats and oils, 387–408 Glycerolysis, 12 Flaxseed oil, 227 Gold of pleasure oil, 236–237, 253 Fluorescence assay Grapeseed oil, 237 for lipid oxidation measurement, 371–373 Grassy flavor, 377t, 421t Foods Grease (animal), See Animal grease antioxidants commonly used in, 441t, 455–474 Green flavor, 421t antioxidant scope of use in, 433–434 Green tea flavonoids, 467, 470–474 fortification for nutrition, 581–582 Groundnut (peanut) oil, 222t, 228 Fourier transform infrared spectroscopy (FTIR) fatty acid composition, 4t, 221t for lipid oxidation measurement, 362–363 saponification equivalent, saponification value, Fractal dimension, fat crystal networks, 137–142 iodine value, and unsaponifiable matter, 10t Fractionation Guaiacol animal fats, 192–193 in sesame oils, 407t vegetable oils, 245–246 Gulf menhaden oil Free fatty acid/acid value, 573 volatile aldehydes, 406t animal fats, 172 Gum guaiac Free radical lipid oxidation initiation, 296–297 acceptable daily intake (ADI), 509t Friedel Crafts acylation, 37–38 Fried food flavor, 421t Hay flavor, 421t Fried foods oil, 237 sensory evaluation, 426–427 Heme proteins Fruity flavor, 421t lipid oxidation initiation, 289–296 Frying fats Hemp , 237 618 INDEX

2,4-Heptadienal Hexane from autooxidation of unsaturated fatty acids, volatile compound in vegetable oils, 395t 391t Hexanoic acid in Gulf menhaden oil, 406t odorant in Irish sour cream butter, 397t sensory characteristics, 392t 2-Hexenal in stored soybean oil, 401t sensory characteristics, 392t trans,cis-2,4-Heptadienal 3-Hexenal volatile compound in vegetable oils, 395t from autooxidation of unsaturated fatty acids, trans,trans-2,4-Heptadienal 391t volatile compound in vegetable oils, 395t cis-3-Hexenal Heptanal in stored soybean oil, 401t sensory characteristics, 392t trans-2-Hexenal volatile compound in vegetable oils, 395t in Gulf menhaden oil, 406t n-Heptanal volatile compound in vegetable oils, in Gulf menhaden oil, 406t 395t Heptane High density lipoproteins (HDL), 593–595 volatile compound in vegetable oils, 395t High erucic rapeseed oil 2-Heptenal fatty acid source, 3t sensory characteristics, 392t High oleic oils, 223 cis-2-Heptenal High-oleic safflower oil, 255 volatile compound in vegetable oils, 395t High-oleic sunflower oil, 255 trans-2-Heptenal Highsun, 232 in Gulf menhaden oil, 406t Homocysteine, 597–598 in lard, 400t Homogeneous nucleation, 57–58 in stored soybean oil, 401t fat crystal networks (anhydrous milkfat), 126, volatile compound in vegetable oils, 395t 127 trans-4-Heptenal Honesty seed oil, 237, 254 in Gulf menhaden oil, 406t Hull-like flavor, 421t Herbicides Hydrocarbons contaminants in fats and oils, 574 from lipid oxidation, 371–373 Heterocyclic amines, 537–538 in vegetable oils, 218 Heterogeneous nucleation, 58 Hydrogenated oil, 377t, 421t fat crystal networks (anhydrous milkfat), 126, Hydrogenation, 535–537 127 animal fats, 185–186 2,4,7,10,13-Hexadecapentaenal fatty acids, 25–27 from autooxidation of unsaturated fatty acids, vegetable oils, 246–248 391t Hydrolyzed animal fat, 174 2,4,7,10-Hexadecatetraenal Hydroperoxides, 387–388, 388–394 from autooxidation of unsaturated fatty acids, decomposition, 18–19, 389–393 391t of fatty acids and their esters, 388–394 2,4-Hexadienal formation by photooxidation, 436 in Gulf menhaden oil, 406t positional distributions in oxidizing fatty acids, Hexanal 300t from autooxidation of unsaturated fatty acids, 11-Hydroperoxylinoleate, 539 390, 391t Hydroxy acid oils, 224 from isomerization of linoleic acid, 313t Hydroxylation odorant in Irish sour cream butter, 397t fatty acids, 22–23 sensory characteristics, 392t Hydroxyl radical, 455 in stored soybean oil, 401t volatile compound in vegetable oils, 395t Idometric titration method, 361–362 n-Hexanal Illipe butter, 235, 237 in Gulf menhaden oil, 406t Inedible beef tallow, 178t in lard, 400t Inedible grease, 178t INDEX 619

Inedible tallow solubility of synthetic antioxidants in, 456t prices between 2000–2003, 181t specifications of commercial grades, 177t Initiation triacylglycerol composition, 8t lipid oxidation, 270, 273–303 volatile flavors from different treatments, Interesterification, 13 400t animal fats, 187–191 worldwide production, 180t vegetable oils, 248–250 Large deformation rheology Iodine value, 9, 172 anhydrous milkfat, 153–154 selected oils, 10t Lauric acid Irish sour cream butter composition in selected animal fats, greases, odorants in, 397t and vegetable oils, 163t Iron formula, 3t catalyst for lipid oxidation initiation, 273–280 in vegetable oils, 221t Isomerization, 535–537 Lauric oils, 222 fatty acids, 32 typical fatty acid composition, 221t Isopropenylpyrazine Lecithin in cocoa butter, 398t acceptable daily intake (ADI), 509t 2-Isopropyl-4,5-dimethyloxazole Lesquerella oil, 238, 254 in cocoa butter, 399t Light 2-Isopropyl-4,5-dimethylthiazole for lipid oxidation initiation, 280–285 in cocoa butter, 399t Light-struck oil, 377t 2-Isopropyl-4-ethyl-5-methyloxazole Lignans, 467, 468 in cocoa butter, 399t Lignoceric acid 2-Isopropyl-3-methylpyrazine composition in selected animal fats, greases, in cocoa butter, 398t and vegetable oils, 163t 2-Isopropyl-4-methylthizaole d-Limonene, 534 in cocoa butter, 399t Linola oil, 227 fatty acid composition, 227t Jojoba oil, 253–254 Linoleic acid, 215–216 composition in selected animal fats, greases, Kapok oil, 237–238 and vegetable oils, 163t 7-Ketocholesterol, 541–542 essential fatty acid, 215–216, 577–578 Ketones formula, 3t from hydroperoxide decomposition, 391–393 hydrogen abstraction rate constants (by t-BuO), Killing-floor fats, 162 314t Kokum oil, 238 isomerization during heating, 313t oxidation propagation mechanism with different Labiatae herb antioxidants, 469–470 solvents, 316t Lanostane, 542t scission products from room temperature Lard, 174 oxidation, 324t antioxidant addition, 195 in vegetable oils, 221t characteristics of meat-fat and meat-vegetable volatile aldehydes from autoxidation, 391t fat, 196t Linoleic acid oils, 222–223 Codex Alimentarius standards, 175t, 176t Linoleic acid paradox, 593 fatty acid composition, 4t, 163t Linolenic acid, 215–216 flavor compounds, 399, 400t composition in selected animal fats, greases, interesterification, 188, 189 and vegetable oils, 163t palmitate in, 170 hydrogen abstraction rate constants (by t-BuO), prices at randomly chosen times in period 314t 2000–2003, 180t scission products from room temperature prices between 2000–2003, 181t oxidation, 324t saponification equivalent, saponification value, in vegetable oils, 221t iodine value, and unsaponifiable matter, 10t volatile aldehydes from autoxidation, 391t 620 INDEX a-Linolenic acid (LNA) phase behavior in crystallization, 46–56 essential fatty acid, 215–216, 577–578, 579– Lipofrac, 192 580 Lipoprotein metabolism, 593–595 formula, 3t Lipoxygenases as n-3 PUFA, 579–580 for lipid oxidation initiation, 285–286 g-Linolenic acid (GLA), 518–520 LNA, See a-Linolenic acid discrimination against in lipase reactions, 15 Long-chain fatty acids, 4 fatty acid composition of oils based on, 234t Long-chain polyunsaturated fatty acids, 578 Linolenic acid oils, 223 Low density lipoproteins (LDL), 593–595 Linseed oil, 222t, 227 Lutein, 463, 507 fatty acid composition, 4t, 221t, 227t secondary antioxidant, 442t fatty acid source, 3t Lycopene, 463, 507 modified by conventional seed breeding, 255 secondary antioxidant, 442t saponification equivalent, saponification value, iodine value, and unsaponifiable matter, 10t Macadamia oil, 238–239 Lipases Mad cow disease, 197–200 for biodiesel production, 201–202 Mahua oil, 239 fatty acid reactions, 13–16 Malic acid for interesterification, 189–191, 249–250 secondary antioxidant, 442t Lipid emulsions Manganese nucleation, 63–64 catalyst for lipid oxidation initiation, 273–277 Lipid hydrolysis (fat splitting) , 239 animal fats, 193–194 Margaric acid Lipid oxidation. See also Antioxidants composition in selected animal fats, greases, free radical autooxidation, 387–388 and vegetable oils, 163t initiation, 270, 273–303 Margarines, 171 integrated reaction scheme, 341–343 Marigold oil, 239 lifetimes and hydrogen abstraction rates of Marine oils various radicals, 288t flavor compounds, 404–407, 406t measurement methods, 357–380 Meadowfoam oil, 239, 253 propagation, 270, 304–333 Meat fats, 161–162 radical chain reaction scheme overview, 269– Meat-fat shortenings, 196t 272 Meat-vegetable fat shortenings, 196t singlet oxygen, 393–394 Medium-chain fatty acids, 4 as target of antioxidants, 432–433 Melon flavor, 421t termination, 270, 333–341 Melon oil, 239 theoretical aspects, 269–343 Melting point Lipid oxidation: measurement methods, 357–380 and quality assurance of fats and oils, 571 Lipid oxidation: theoretical aspects, 269–343 Metal deactivators, 442–443 Lipid oxidation products, 539–541 Metallic flavor, 421t Lipids 4-Methyl-cholestane, 542t in animal fats, 161–171 2-Methyl-4,5-dibutyloxazole bioactive lipid-soluble constituents, 533–535 in cocoa butter, 399t biological functions, 577, 578–579 2-Methyl-6,7-Dihydro-5H-cyclopentapyrazine bond energies of hydrogens in acyl chains, 297t in cocoa butter, 398t composition of anhydrous milkfat, 123–125, 2-Methyl-4-ethyl-5-butyloxazole 124t in cocoa butter, 399t and endothelial cell dysfunction, 595, 599 2-Methyl-4-ethyl-5-propyloxazole energies of light at various wavelengths vs. in cocoa butter, 399t typical energies of bonds, 281t Methyl linolenate interaction with xenobiotics and chronic product distribution of autooxidized at 40C, disease, 516 309t modification, 244–259 solubility of synthetic antioxidants in, 456t INDEX 621

3-Methyl-2,4-nonanedione composition in selected animal fats, greases, in stored soybean oil, 401t and vegetable oils, 163t Methyl octanoate formula, 3t from isomerization of linoleic acid, 313t in vegetable oils, 221t Methyl oxononanoate Myristoleic acid from isomerization of linoleic acid, 313t composition in selected animal fats, greases, 2-Methyl-3-pentylpyrazine and vegetable oils, 163t in cocoa butter, 398t Methylpyrazine Natural antioxidants, 20, 456t, 460–474 in cocoa butter, 398t regulatory status, 503–508 Methyltrioxorhenium (MTO) catalyts, 21–22 Natural fats 2-Methyl-5-vinylpyrazine crystallization, 46 in cocoa butter, 398t polymorphism, 78, 108–115 2-Methyl-6-vinylpyrazine Natural oils in cocoa butter, 398t polymorphism, 78, 113–115 Microstructure Neem oil, 240 fat crystal networks, 135–148 Nervonic acid Milkfat. See also Anhydrous milkfat composition in selected animal fats, greases, mechanical properties, 122–123 and vegetable oils, 163t polymorphism, 108–110, 131–134 Networks, fat crystal, 121–158 Milkfat globle cream Nickel thermal and structural behavior compared to as catalyst for fatty acid hydrogenation, 26 anhydrous milkfat, 110t Nigella oil, 240 Mixed-acid triacylglycerols Niger oil, 240 defined, 78 2,4-Nonadienal polymorphism in, 90–100 in Gulf menhaden oil, 406t Monene acids, 215–216 in stored soybean oil, 401t Monoacid triacylglycerols 2,6-Nonadienal defined, 78 in Gulf menhaden oil, 406t polymorphism, 85–90 3,6-Nonadienal polymorphism in, 85–90 from autooxidation of unsaturated fatty acids, Monoacylglycerol citrate 391t regulations governing use, 480t cis,cis-3,6-Nonadienal Monoacylglycerols, 9 odorant in Irish sour cream butter, 397t crystallization, 46, 47 trans,cis-2,4-Nonadienal quality assurance of fats and oils, in stored soybean oil, 401t 568–569 trans,trans-2,4-Nonadienal Monoglycerides, See Monoacylglycerols odorant in Irish sour cream butter, 397t Monoisopropyl citrate in stored soybean oil, 401t regulations governing use, 480–481t Nonanal Monola, 230 from autooxidation of unsaturated fatty acids, Monoterpenes, 534–535 391t Monounsaturated fatty acids, 243, 517–518 sensory characteristics, 392t adverse effects, 517–518 volatile compound in vegetable oils, 395t Mowrah oil, 239 n-Nonanal Mustard oil, 239 in Gulf menhaden oil, 406t Musty flavor, 421t in lard, 400t Mutton fat Nonatrienal positional distribution of fatty acids in, 169t in Gulf menhaden oil, 406t Mutton tallow, 162 Nondirected interesterification, 188 fatty acid composition, 163t Nonedible tallow, 181 b-Myrcene, 535 prices at randomly chosen times in period Myristic acid 2000–2003, 180t 622 INDEX

2-Nonenal cis-2-Octenal sensory characteristics, 392t in Gulf menhaden oil, 406t 3-Nonenal in stored soybean oil, 401t from autooxidation of unsaturated fatty acids, trans-2-Octenal 391t in Gulf menhaden oil, 406t cis-2-Nonenal in lard, 400t odorant in Irish sour cream butter, in stored soybean oil, 401t 397t Octene in stored soybean oil, 401t volatile compound in vegetable oils, 395t cis-3-Nonenal 1-Octen-3-hydroperoxide in stored soybean oil, 401t in stored soybean oils, 401t, 402t trans-2-Nonenal 1-Octen-3-ol, 393 in Gulf menhaden oil, 406t in lard, 400t in lard, 400t volatile compound in vegetable oils, 395t odorant in Irish sour cream butter, 397t 1-Octen-3-one, 391 in stored soybean oil, 401t odorant in Irish sour cream butter, 397t Nuclear magnetic resonance (NMR) spectroscopy in stored soybean oils, 401t, 402t for lipid oxidation measurement, 375–376 Octyl gallate, 440 Nucleation, 47, 57–64 antioxidant commonly used in foods, 459 anhydrous milkfat, 126–131, 146–148 regulatory status, 497–498 NuSun, 232 Oenothera biennis linn oil, 518–519 fatty acid composition, 221t Oil-containing foods oil, 240 sensory evaluation, 426 Nutty flavor, 377t, 421t Oil palm, 255 Oils. See also Vegetable oils Oats adverse effects of natural constituents of, plant sterol source, 523t 530–533 Oats oil, 240 adverse products from overheated, 543–545 2,4-Octadienal characteristics, 571 in Gulf menhaden oil, 406t composition, 568–569 cis-1,5-Octadien-3-hydroperoxide crystallization of, 45–73 in stored soybean oil, 401t, 402t fatty acid composition of major commodity, 4t cis-1,5-Octadien-3-one fatty acids in commodity, 3t in stored soybean oil, 401t, 402t flavor components, 387–408 g-Octalactone manufacturing hazards in processing, 550–552 in lard, 400t oxidation and antioxidant mechanisms, odorant in Irish sour cream butter, 397t 434–436 Octanal plant sterol sources, 523t from autooxidation of unsaturated fatty acids, polymorphism in, 77–116 391t quality assurance of, 565–574 sensory characteristics, 392t quality parameters, 568t in stored soybean oil, 401t saponification equivalent, saponification value, volatile compound in vegetable oils, 395t iodine value, and unsaponifiable matter of n-Octanal major commodity, 10t in Gulf menhaden oil, 406t sensory evaluation, 423–426 in lard, 400t toxicity and safety, 513–552 Octane toxic substances produced during smoking, volatile compound in vegetable oils, charbroiling, and barbecuing, 545–547 395t volatile compounds in commercial, 395–408 Octenal worldwide production, 180t volatile compound in vegetable oils, 395t Oilseeds 2-Octenal antioxidants from, 467–474 sensory characteristics, 392t Oil stability index, 370–371 INDEX 623

Oiticica oil, 240 formula, 3t Olefin metathesis, 34–36 in vegetable oils, 221t oils, 222 ball and stick model, 6 Palmitoleic acid composition in selected animal fats, greases, composition in selected animal fats, greases, and vegetable oils, 163t and vegetable oils, 163t formula, 3t 1,3-Palmitoyl-2-oleoyl-sn-glycerol (POP), 96, 96t hydrogen abstraction rate constants (by t-BuO), , 222, 222t, 229 314t fatty acid composition, 4t scission products from room temperature fatty acid source, 3t oxidation, 324t fractionation, 246 in vegetable oils, 221t saponification equivalent, saponification value, volatile aldehydes from autoxidation, 391t iodine value, and unsaponifiable matter, 10t Oleic acid oils, 222–223 typical fatty acid composition, 221t Oleic oils, 252 worldwide production, 180t Oleins, 245 Palm oil, 222t, 228–229 Oleochemicals, 27–32 fatty acid composition, 4t, 221t, 228t Olestra, 532 fatty acid source, 3t Olive oil, 222t, 227–228 fractionation, 246 fatty acid composition, 4t, 221t polymorphism, 113–115 fatty acid source, 3t prices at randomly chosen times in period flavor compounds, 404 2000–2003, 180t saponification equivalent, saponification value, prices between 2000–2003, 181t iodine value, and unsaponifiable matter, 10t saponification equivalent, saponification value, triacylglycerol composition, 8t iodine value, and unsaponifiable matter, volatile compounds in, 395t 10t worldwide production, 180t worldwide production, 180t g-Oryzanol, 469, 531 Palm olein Oven storage test, 451 fatty acid composition, 221t, 228t Overheated oil, 421t Palm stearin Oxidation. See also Autooxidation; Lipid fatty acid composition, 221t, 228t oxidation Parsley oil, 240 and antioxidant mechanism, 434–436 Passionfruit oil, 240 fatty acids, 16–25 Peanut oil, 222t, 228, 229 Oxidative cleavage fatty acid composition, 4t, 221t fatty acids, 23–25 saponification equivalent, saponification value, Oxidative quality/stability tests, 572–573 iodine value, and unsaponifiable matter, Oxidized oil, 377t, 421t 10t Oxidograph, 360 volatile compounds after 8 days at 60C, 395t Oxygen scavengers, 443 worldwide production, 180t Oxyl radical 3,6,9,12-Pentadecatetraenal ease of abstraction with various double bond from autooxidation of unsaturated fatty acids, configurations, 329t 391t Ozone 3,6,9-Pentadecatrienal fatty acid oxidative cleavage, 23–24 from autooxidation of unsaturated fatty acids, for lipid oxidation initiation, 286–289 391t Pentanal Packaging materials sensory characteristics, 392t potential hazards of, 549–550 volatile compound in vegetable oils, 395t Painty flavor, 377t, 421t n-Pentanal Palmitic acid in Gulf menhaden oil, 406t composition in selected animal fats, greases, Pentane and vegetable oils, 163t volatile compound in vegetable oils, 395t 624 INDEX

Pentanoic acid and quality assurance of fats and oils, 570 in stored soybean oil, 401t sources in oils and cereals, 523t Pentanol Plastics volatile compound in vegetable oils, 395t potential hazards of packaging materials, Pentenal 549–550 volatile compound in vegetable oils, 395t Polarized microscopy cis-2-Pentenal fractal dimension of fat crystal networks, in Gulf menhaden oil, 406t 142–148 Pentene Polar lipids, 570 volatile compound in vegetable oils, 395t Pollutants 1-Penten-3-ol contaminants in fats and oils, 574 volatile compound in vegetable oils, 395t Polychlorinated biphenyls (PCBs), 515 1-Penten-3-one adverse health effects, 550–551 odorant in Irish sour cream butter, 397t in fats and oils, 574 2-Pentylfuran, 393 Polycyclic aromatic hydrocarbons (PAHs), 514 in lard, 400t from smoking, charbroiling, and barbecuing, volatile compound in vegetable oils, 395t 545–547 2-Pentylthiazole in vegetable oils, 218–219 in cocoa butter, 399t Polyene acids, 215–216 Perilla oil, 240 Polymers Peroxide value, 172, 361–364 and quality assurance of fats and oils, 573 and quality assurance of fats and oils, 572–573 Polymorphism (genetic), 585–586 Peroxisome proliferator-activated receptors Polymorphism in fats and oils, 77–116 (PPARs), 579, 584–585, 598 and crystallization, 48–51 Peroxyl radical, 272, 297–303 fat crystal networks (anhydrous milkfat), Peroxy radical, 434 131–134 Pesticides fat mixtures, 100–108 contaminants in fats and oils, 574 mixed-acid triacylglycerols, 90–100 Petroselinic acid monoacid triacylglycerols, 85–90 in vegetable oils, 221t natural fats, 108–115 Petroselinic acid oils, 252–253 triacylglycerols (TAGs), 78–85 Phenolic acids, 467–468 Polyphosphates, 442 antioxidant commonly used in foods, 441t n-3 Polyunsaturated fatty acids (n-3 PUFAs), Phenoxy radical, 439 518–520, 578, 579–580 (3-N-Phenylamino)-1,2-propanediol (PAP), 551 biochemistry, 582 Phosphates food fortification with, 581–582 acceptable daily intake (ADI), 509t mode of action against atherosclerosis, secondary antioxidant, 442t 592–593 Phospholipids, 570 mode of action against chronic disease, crystallization, 46, 47 587–589 defined, 9 n-6 Polyunsaturated fatty acids (n-6 PUFAs), 518, in vegetable oils, 217 577–578 Photooxidation, 435–436 mode of action against atherosclerosis, 593 fatty acids, 17–20 Polyunsaturated fatty acids (PUFA), 243, 244 Phytic acid, 442 adverse effects, 518–520 Phytoestrogens, 533–534 biochemistry, 582–583 Phytosterols, See Plant sterols essential fatty acids used for production, 578 Pig fats, 161 hydrogen abstraction rate constants (by t-BuO), Pine flavor, 421t 314t Pistachio oil, 241 Poppy oil, 241 Plant lipids, 165 Pork fat Plant sterols (phytosterols), 468–469, 522–525 influence of diet on fatty acid composition, 166t classification, 542t positional distribution of fatty acids in, 169t INDEX 625

Porphyrins Rapeseed oil (high erucic) lipid oxidation initiation, 289–296 fatty acid composition, 221t Poultry fats, 161, 178 Rapeseed oil (low erucic) specifications of commercial grades, 177t fatty acid composition, 221t Premier Jus, 174 Raw oil, 421t Codex Alimentarius standards, 175t, 176t Reactive nitrogen species, 492 Primary antioxidants, 436–441 Reactive oxygen species, 491 Prime steam lard, 183 Recovered , 178t Prime tallow Reducing agents, 443 specifications of commercial grades, 177t Reducol, 526 Prions, 197–198 Reduction Propagation fatty acids, 25–27 lipid oxidation, 270, 304–333 Reduction potential, 439t Propanal Refined and bleached color, 172 from autooxidation of unsaturated fatty acids, Refractive index 391t and quality assurance of fats and oils, 571 volatile compound in vegetable oils, 395t Rendered pork fat, 161, 174 Propane Codex Alimentarius standards, 175t, 176t volatile compound in vegetable oils, 395t Rendered tallow, 178t Propenal Rendering, 182–184 volatile compound in vegetable oils, 395t Reverted oil, 377t, 421t Propylene glycol Rice bran solubility of synthetic antioxidants in, 456t plant sterol source, 523t Propyl gallate, 20, 440 Rice bran oil, 230, 531 acceptable daily intake (ADI), 509t fatty acid composition, 221t antioxidant commonly used in foods, 441t, 459 Ricinoleic acid, 531–532 effect on oxidation of soybean oil, 458t in vegetable oils, 221t maximum level permitted, 501t Ricolenic acid, 4 physical properties, 456t Room odor, sensory evaluation, 426 properties, applications, and regulations, 500t Rosemarinic acid, 469 regulations governing use, 481t Rubber seed oil, 531 regulatory status, 497–498 Rubbery flavor, 421t Prostanoids, 582–583 Rumen-mediated fatty acid modification, 165–167 Pro-vitamins, 506 Ruthenium oxide PUFA, See Polyunsaturated fatty acids fatty acid oxidative cleavage catalysis, 24–25 Purslane oil, 241 Rye plant sterol source, 523t Quality assurance of fats and oils, 565–574 Safflower oil, 222t, 230 Rancid flavor, 421t fatty acid composition, 221t Rancid oil, 377t high-oleic, 255 Rapeseed oil, 229 volatile compounds after 8 days at 60C, 395t fatty acid composition, 4t, 163t Safflower oil (high oleic) fatty acid source, 3t fatty acid composition, 221t genetically modified, 257 Saffola, 230 influence of diet on fatty acid composition of SALATRIM, 532 pork and beef fat, 166t Sal fat oil, 241–242 modified by conventional seed breeding, Saponification equivalent 254–255 selected oils, 10t plant sterol source, 523t Saponification value, 9, 173 saponification equivalent, saponification value, selected oils, 10t iodine value, and unsaponifiable matter, 10t Sardine oil worldwide production, 180t flavor compounds, 404 626 INDEX

Saturated fatty acids anhydrous milkfat, 148–152 adverse effects, 243, 515–517 fractal dimension of fat crystal networks, 137– in animal fats, 165–168 142 de novo synthesis, 214–215 Small deformation rheometry, 148 Saturated mixed acid triacylglycerols Smoke point polymorphism, 90–93 and quality assurance of fats and oils, 571 Saturated monoacid triacylglycerols Smokey flavor, 421t polymorphism, 85–87 Smoking Saturated-unsaturated mixed acid triacylglycerols toxic substances produced by, 545–547 polymorphism, 94–99 Sodium ascorbate, 505 Scrapie, 197 Sodium erythorbate Sea buckthorn oil, 241 secondary antioxidant, 442t Secoisolariciresinol diglucoside (SDG), 468 Solid fat content Secondary antioxidants, 437, 441–443 fat crystal networks (anhydrous milkfat), 127– Secondary nucleation, 58–60 131 fat crystal networks (anhydrous milkfat), 126, Solid-solution mixtures, 82–84 127 Sour flavor, 421t Seeding, 70–71 Soybean oil, 222t, 231 Sensory evaluation, 413–427 aroma extract analysis of stored, 401t fried foods, 426–427 effect of antioxidants, 458t frying oils, 426 fatty acid composition, 4t, 163t, 221t lipid oxidation measurement, 376–377 fatty acid source, 3t oil-containing foods, 426 flavor compounds, 400–402, 401t, 402t oils, 423–426 genetically modified, 257 Sensory evaluation test facility, 416–418 hydroperoxides and epoxides in stored, 402t Sequestering agents, 442–443 influence of diet on fatty acid composition of Sesame oil, 222t, 231 pork and beef fat, 166t adulteration quality assurance, 574 prices at randomly chosen times in period effect of seed roasting time on odorants, 407t 2000–2003, 180t fatty acid composition, 4t, 221t prices between 2000–2003, 181t fatty acid source, 3t saponification equivalent, saponification value, flavor compounds, 407t, 407–408 iodine value, and unsaponifiable matter, 10t saponification equivalent, saponification value, triacylglycerol composition, 8t iodine value, and unsaponifiable matter, 10t volatile compounds after 8 days at 60C, 395t Sesamin, 468 worldwide production, 180t Sesaminol, 468 Special tallow Sesamol, 468 specifications of commercial grades, 177t Sesamolin, 468 Specialty vegetable oils, 232–242 Shea oil, 241 Sphingolipids, 570 Sheep fats, 161, 162 Stale flavor, 421t Shelf storage test, 450 Short-chain fatty acids, 4 ball and stick model, 6 Shortenings composition in selected animal fats, greases, animal fat-based, 195–197, 196t and vegetable oils, 163t characteristics of meat-fat and meat-vegetable formula, 3t fat, 196t in vegetable oils, 221t Signal transduction Stearidonic acid role of fats in, 583–584 essential fatty acid, 578, 579 Single nucleotide polymorphism (SNP), 585–586 Stearins, 245 b-Sitosterol, 473, 524 Sterols, 213, 521–527 Skatole in vegetable oils, 217–218 odorant in Irish sour cream butter, 397t Stigmasterol, 524 Small deformation rheology Stigmasteryl ferulate, 473 INDEX 627

Stillingia oil, 235 worldwide production, 180t Structured lipids, 191 Tallow fatty acid composition, 4t Structured triacylglycerols, 532–533 Tartaric acid Succinic acid acceptable daily intake (ADI), 509t secondary antioxidant, 442t secondary antioxidant, 442t Sulfation TBHQ, See tert-Butylhydroquinone fatty acids, 29 Termination Sulfites lipid oxidation, 270, 333–341 acceptable daily intake (ADI), 509t Terpenes, 213 secondary antioxidant, 442t a-Terpinene, 534 a-Sulfonates, 29–30 g-Terpinene, 534 Sulfur flavor, 421t Terpinolene, 534 Sunflower oil, 222t, 231–232 5,6,7,8-Tetrahydroquinoxaline fatty acid composition, 4t, 221t in cocoa butter, 398t fatty acid source, 3t Tetramethylpyrazine genetically modified, 257 in cocoa butter, 398t high-oleic, 255 Thermal oxidation, 435 saponification equivalent, saponification value, Thermoxidized palm oil (TPO), 543–545 iodine value, and unsaponifiable matter, 10t Thiobarbituric acid test, 366–367 volatile compounds after 8 days at 60C, 395t Thiobarbituric acid value, 573 worldwide production, 180t Tierkupper, 178t Sunola, 232 Titer, 173 fatty acid composition, 221t and quality assurance of fats and oils, 571 Superoxide dismutase, 443 Tobacco seed oil, 241–242 Superoxide radical, 455 a-Tocopherol, 20, 464–465, 465t, 504 Surface active compounds effect on oxidation of soybean oil, 458t fatty acid based, 27–32 mechanism, 466 Synthetic antioxidants, 20, 456t, 457–459 regulations governing use, 482t physical properties, 456t b-Tocopherol, 464–465, 465t, 504 regulations governing in Canada and U.S., g-Tocopherol, 464–465, 465t, 504 477–482t d-Tocopherol, 464–465, 465t, 504 regulatory status, 492–503 Tocopherols, 20 acceptable daily intake (ADI), 483t, 509t TAG, See Triacylglycerols antioxidants commonly used in foods, 441t, Tall oil, 231–232 464–465 fatty acid composition, 232t regulations governing use, 482t Tall oil , 232 regulatory responsibilities, 502t Tallow, 161–162, 181–182 regulatory status, 504–505 antioxidant addition, 195 in vegetable oils, 218 characteristics of meat-fat and meat-vegetable a-Tocotrienol, 464, 465t, 504 fat, 196t b-Tocotrienol, 464, 465t, 504 fatty acid composition, 163t g-Tocotrienol, 464, 465t, 504 fatty acid source, 3t d-Tocotrienol, 464, 465t, 504 influence of diet on fatty acid composition of Tocotrienols pork and beef fat, 166t antioxidant commonly used in foods, 441t, naming conventions for inedible, 178t 464–465 prices at randomly chosen times in period regulatory status, 504–505 2000–2003, 180t Top white tallow prices between 2000–2003, 181t specifications of commercial grades, 177t saponification equivalent, saponification value, Totox value, 369 iodine value, and unsaponifiable matter, 10t Toxicity and safety of fats and oils, specifications of commercial grades, 177t 513–552 trading grades for technical, 177t Toxic oil syndrome, 551–552 628 INDEX

Transcription factors in mixtures, 101–104 role of fats in, 584 occurrence in TAGs, 100t Transesterification, 187–188 Trolox, 380 Triacid triacylglycerols, 78 Tropical oils, 220

Triacylglycerol C10C12C10 worldwide production, 180t unit cell parameters, 92t Tung oil, 222t, 242

Triacylglycerol C16C16C14 unit cell parameters, 92t Ultraviolet light Triacylglycerols for lipid oxidation initiation, 280–282 in animal fats, 162–171 2,4-Undecadienal chain length structure, 81–82 in Gulf menhaden oil, 406t composition of fat crystal networks (anhydrous Undecanal milkfat), 123–125, 124t sensory characteristics, 392t composition of selected commodity oils, 8t Undecenal crystallization, 46, 57–68 volatile compound in vegetable oils, 395t crystallization control, 68–73 2-Undecenal formation, 216–217 from autooxidation of unsaturated fatty acids, lipid phase behavior, 46–56 391t phase equilibria, 82–84 sensory characteristics, 392t polymorphic form occurrence, 100t Unsaponifiable matter, 9, 570–571 polymorphism, 48–51, 78–85 animal fats, 172 polymorphism in mixed-acid, 90–100 selected oils, 10t polymorphism in monoacid, 85–90 Unsaturated fatty acids polymorphism in natural fats, 108–115 in animal fats, 165–168 positional distribution in animal depot fats, 169t Unsaturated monoacid triacylglycerols quality assurance of fats and oils, 568–569 polymorphism, 88–90 subcell structure, 80–81 thermal stability, 79–80 2-Vaccinoyl glycerol (OVO), 98–99 Tricaprin (CCC) Vanadium unit cell parameters of b form, 86t catalyst for lipid oxidation initiation, 274–277 2,4,7,10-Tridecatetraenal Variant Creutzfeldt-Jacob disease (vCJD), 198 from autooxidation of unsaturated fatty acids, Vegetable butters, 223 391t Vegetable oils, 213–259 2,4,7-Tridecatrienal and animal fat market, 179 from autooxidation of unsaturated fatty acids, biosynthesis, 213–217 391t classification, 219–242 Trielaidoyl-glycerol (EEE) common fatty acids in, 221t occurrence in TAGs, 100t by fatty acid type, 222t , See Triacylglycerols fractionation, 245–246 Trihydroxybutyrophenone (THBP), 503 hydrogenation, 246–248 Trilaurin (LLL) minor components, 217–219 in mixtures, 101–104 modification, 242–257 unit cell parameters of b form, 86t worldwide production, 180t Trimethylpyrazine Vernolic acid, 4, 224, 254 in cocoa butter, 398t in vegetable oils, 221t Triolein Vernolic oil, 222t polymorphism, 88t Very low density lipoproteins (VLDL), Trioleoyl-glycerol (OOO) 593–594 occurrence in TAGs, 100t Vitamin A, 527–528 Tripalmitin (PPP) Vitamin C, 460. See also Ascorbic acid in mixtures, 101–104 Vitamin D, 529–530 unit cell parameters of b form, 86t Vitamin E, 528–529. See also Tocopherols Tristearoyl-glycerol (SSS) Vitamin K, 530 INDEX 629

Walnut oil, 242 White grease, 162 Water fatty acid composition, 163t solubility of synthetic antioxidants in, prices between 2000–2003, 181t 456t specifications of commercial grades, 177t Watermelon flavor, 377t Woody flavor, 421t Waxy flavor, 421t Weedy flavor, 421t Yellow grease, 162, 175, 178t Wet fractionation, 192–193 fatty acid composition, 163t Wheat prices between 2000–2003, 181t plant sterol source, 523t specifications of commercial grades, 177t Wheat germ Yu-Cheng disease, 551 plant sterol source, 523t Wheatgerm oil, 242 Zeaxanthin, 506