Index

a-anions 221 anti-block agent 218, 237 acetate 23, 106 antioxidants 84, 173, 175, 176 acetate-malonate pathway 24 anti-slip agent 218, 237 acetylenic acids 10, 11, 159 Apis mellifera 85 acetylenic intermediates 30 apricot 66, 67 acid anhydrides 214 5, 6 acid chlorides 214 8,9, 29, 184 acidity 102 synthesis 31, 32 acidolysis 208,209, 213 Arachis hypogaea 67 ACP, see acyl carrier protein argentation tic 19 activated carbon 90 arsenites 18 acyl carrier protein 25 asci epic acid 7 acylation 47 Aspergillus niger 88, 97, 213 acylglycerols 36, 52 Aspergillus oryzae 213 acylpyrrolidide 154 auricolic acid 13, 14 alchornoic acid 15 autoxidation 162-167 alcohols 217,238 avenasterol 84 alcoholysis 208, 209 67 alepramic acid 14 aziridines 202 aleprestic acid 14 alepric acid 14 babassu oil 88 aleprolic acid 14 72 aleprylic acid 14 beeswax 84 Aleurites fordii 10 5, 6 alkanoic acids, crystal structure 130 bentonitite 90 alkylbenzoxazole 154 benzyl-sn- 54 alkyl dimethyloxazole 154 benzylidene glycerol 48 alkyl ketene dimers (AKD) 215 Betapol 55, 214 alkyl polyglucoside 217 BHA, see butylated hydroxyanisole allenic acids 10, 11, 39 BHT, see butylated hydroxy toluene allenic epoxides 187 biodiesel 241 allylic bromination 194 biohydrogenation 161 alklylic hydroperoxides 162, 163, 165 biosynthesis 24, 44 oil 66, 67, 69 blackcurrant oil 64, 65 alternation 130 bleaching 89, 90 amides 218, 238 Bligh and Dyer method 101 amine oxides 219, 220, 237 BOB, see oleodibehenin amines 219,220,237 boiling point 5 amphiphilic 234 bolekic acid 11 amphoterics 219, 237 borage oil 64, 65 analytical procedures 100 Borago officinalis 65 see also specific types of borates 18 anchovy oil 72, 74 Borneo tallow 66 anhydrous milk 96 bovine milk phosphatidylcholines 122 animal 72 branched-chain acids 12, 85 anionic surfactants 205, 237 Brassica alba 79 anisidine value 103, 104 Brassica campestris 68 annual crops 61 Brassica napus 68 anteiso acids 12, 26 brassicasterol 84 INDEX 245 bromination 193, 194 chromatography see specific forms of bromo acids 193 chromatorods 106 butanoic acid 4, 5, 25, 230 chrysobalanic acid 10 63, 229, 233 Chrysobalanus icaco 10 butterfat 63, 71 chylomicrons 224, 225 butylated hydroxyanisole 176, 177 citric acid 179 butylated hydroxytoluene 176 13C_nmr chemical shifts 144--146 butyl peroxyester 215, 216 CoA esters 25 4,5,230 65, 66, 75, 120, 124, 137 Butyrivibrio fibrosolvens 161 polymorphism 138 Butyrospermum parkii 66 substitute 213 by-products, as 61 62, 63, 65,66, 174 glycerol esters 114 caffeic acid 179 Cocus nucifera 66 calendic acid 10 72, 74, 174 Calendula officinalis 10 cod roe 83 calendula oil 80 columbinic acid 10 campesterol 84 complex lipids 35 camJclilla wax 84 component acids 69, 106 Candida cylindricae 97, 213 compound formation 134 Candida rugosa 207 confectionary fats, crystal structure 137 174 conjugated polyene acids 9 capelin oil 72, 74 Copernica cerifera 85 caper spurge 79 copra 66,88 Caprenin 56,213 coriolic acid 15 5 com oil 62, 63, 66, 69, 88, 174 5 Cornyebacterium acnes 94, 213 5 coronaric acid 15 carbon}i compounds, infrared absorption 62, 63, 66, 69, 76, 88. 174 139 cow milk fat 71 carboxyl group reactions 205, 220 Crambe abyssinicum 79 camauba wax 84 CrlllllIDe oil 79 camosic acid 179 crepenyic acid 10, 11 carotenes 82, 179 Criegee zwitterion 190 carrot 146 crystal form of glycerol esters 134, 135, Carthamus tinctorius 70 233 13, 14, 62, 63, 65, 153 crystallisation 17 Catalpa ovata 10 crystallographic data 132 catalpic acid 10 Cuphea sp. 78 cationic surfactants 205, 237 cutins 43 Cephalocroton cordofanus 15 cyclic acids 12 ceramides 36, 44, 46. 47 cyclisation 198 cerebroside, biosynthesis of 46 cyclopentene acids 13, 14,26 cerebrosides 36, 44 cyclopropane acids 203 cetoleic acid 7, 8 cyclopropene acids 181, 203 chain elongation 26 chaulmoogric acid 14 DAG, see diacylglycerols, synthesis of chemical shifts dairy spreads 232 13C 144, 145. 146 DCL (double chain length) structures IH 142 133,136 124 de novo biosynthesis 23, 25 chlorination 193 decanoic acid 5 chloro acids 193 degumming 89,90 chlorophyll 82 dehalogenation 195 chocolate 65 dehydrated castor oil 14 cholesterol 83 dehydrocrepenyic acid 11 oxidation 171 dehydrohalogenation 195 chromatographic refining 90 demospongic acids 10 246 INDEX densipolic acid 13, 14 elaido glycerides 93 deodorisation 89, 90 electron-impact mass spectroscopy 147, desaturation 27 148 deuterated acids, synthesis 31 electron spin resonance spectra 138 DGDG, see digalactosyldiacylglycerols eleostearic acid 10 DHA, see emulsifiers 234 diacyl peroxides 215, 216 endogenous fat 223 diacylglycerols 37,41 enzymes 97, 205 crystal structure 136 enzymic hydrolysis 41 synthesis 50, 51, 55 enzymic interesterification 97, 212 diamides 218, 239 enzymic oxidation, mechanism of 185 diamines 219, 220 EPA, see diazomethane 208 epithiostearic acid 202 dibasic acids 238, 240 epoxidation 186, 187 diepoxystearic acid 186 epoxide 189 dietary guidelines 226 epoxidised oils 147 dietary intake 226, 227 epoxy acids 15, 185-188 differential scanning calorimetry 129 epoxy oils 81 digalactosyldiacylglycerols 36, 39 epoxypropanol 48 diglycerides, see diacylglycerols epoxystearic acid 186 dihomo-y-linolenic acid 8, 29, 30 equivalent chain length 20, 21, 111 dihydroxystearic acid 189 Erlanga tomentosa 15 dilatometry 129 7,68,79,225 dimer acids 173, 200, 238 erythrogenic acid 11 dimer alcohols 217 essential fatty acids 223 dimerisation 200 ester waxes 43 dimorphecolic acid 15, 81 ester--ester interchange 208 dimorphotheca oil 81 esterification 207, 208 diols 189, 190 estolide 201 diphytanylglycerol 43 ethanediol esters 43 directed interesterification 97 ethanolamides 237 distillation 17 ether lipids 42 docosahexaenoic acid 8, 9, 29, 208 ether sulphate 217 docosanoic acid 5 ethoxylate 217 8, 28, 29 ethoxylated amides 218 docosenoic acid 7 ethylene diamine tetra- 179 dodecanoic acid 5 ethylene oxide adducts 219 do,~lble bond migration 92, 198 Euphorbia antisphylitica 85 doxylstearic acid 138 Euphorbia lagascae 15, 81 D P A. see docosapentaenoic acid Euphorbia lathyris 79 dry fractionation 95 even acids - polymorphism 132 evening primrose oil 64, 65 E numbers 177 exocarpic acid 11 EeL, see equivalent chain length exogenous fat 223 EDTA, see ethylene diamine tetra-acetic exotic oils 66 acid extraction 87, 88 EFA efficiency 28 egg lipids 82 factice 241 egg phosphatidylcholines 122 FAS, see synthetase eicosanoic acid 5 fat spreads 232 eicosanoid cascade 185 fats eicosanoid metabolites 29 absorption 224 eicosanoids 184 daily intake 62, 226, 227 eicosapentaenoic acid 8, 9, 29, 203 digestion 224 eicosatetraenoic acid, synthesis 31 splitting 207 eicosenoic acid 7 transport 224 Elaeis guinensis 68 use 241 7 fatty acid synthetase 25 INDEX 247

biosynthesis 23 half-fat 232 composition 73 half-hydrogenated intermediate 160 fatty acids halogenation 192 chemical synthesis 28 oil 67 cosmetic uses 238 HDL (high density lipoprotein) 225 dietary intake 227 helenynolic acid 10, 15 identification 16 Helianthus annus 70 isolation 16 heptanal 14 structure 3 herring oil 72,73,127, 174 62,63,72. 73 hexadecanoic acid 5 Flacourtiaceae, seed fats 13 hexadecenoic acid 7 flavour 165 hexahydroxystearic acid 189 fluoro- 16 hexanoic acid 5 fluoropalmitic acid 16 high-performance liquid chromatography Folch method 101 106, 109, 110, 114, 117, 119 food grade emulsifiers 235 higher monoene acids 79 Fourier transform infrared spectrometers HighSun oil 71 138 IH-nmr, chemical shifts 143 fractionation 95 honesty seed oil 8, 79 Friedel-Crafts reaction 203 hormelic acid 14 frying oils 234 HPLC, see high-performance liquid Fuller's earth 90 chromatography furanoid acids 15 human milk fat 71,73, 155,214 hydnocarpic acid 14 7 hydrazine reduction 159, 161 gallic esters 177 hydroformylation 203 gangliosides 36, 44 hydrogenated fats 147 gas chromatography 106, 111, 112, 113, hydrogenation 22, 89, 91, 157, 158, 160 115, 116 hydrogenolysis 217 Geotrichum candidum 97, 213 hydrolysis 206 GLA, see y-linolenic acid hydroperoxide 166-168, 185, 191 glycerides 36 hydrophilic regions of soap 236 glycerol dibehenate oleate 55 hydrophilisation 96 glycerol dioleate palmitate 55 hydrophobic regions of soap 236 glycerol esters hydroxy acids 13, 14,81, 185 biosynthesis 46 hydroxydecanoic acid 14 crystal structure 133 hydroxylation 189 glycerol monostearate 235 hyproperoxide lyase 183 glycerol triesters 133 glycerol tristearate 131 Iatroscan 106 glycerolysis 208, 210, 234 illipe butter 66 glyce;rophosphoric acid 39 imidazolines 219, 220 glycerophosphorylcholines 41 Impatiens balsamina 10 glycidol 48 infrared spectroscopy 129, 138, 139 Glycine max 70 inks 240 glycosyldiacylglycerols 39 interchangeability of oils and fat~ 76 glycosylglycerides 36 interesterification 96,97,208,210,211, gondoic acid 7 213 gorlic acid 14 invisible fat 223 Gossypium hirsutum 66 iodolactonisation 193 gourmet oils 66 isanic acid 11 GPC, see glycerophosophorylcholines isanolic acid 15 grapeseed oil 67 iso acids 12, 26 groundnut oil 62,63,67,69,76,88 isopropyl esters 108 Guerbet acids 201, 217 isopropylidine glycerol 48, 53, 55 Guerbet alcohols 201, 217 isoricinoleic acid 14 isostearic acid 201 half-fat butter 232 isotopically labelled acids, synthesis 32 248 INDEX

Jacaranda mimosifolia 10 Mallotus phillipinensis 10 jacaric acid 10 malonare 23 Jessenia 79 malvalic acid 13, 181 jojoba oil 8, 43, 79, 84 manaoic acid 14 margarine 97, 137, 232 kamlolenic acid 10 marigold oil 80 Koch reaction 203 mass spectrometry 147,150, 152, 154 kusum 6 MS-MS 154 MCT, see medium chain laballenic acid 11 Mead's acid 8, 9, 28 lactobacillic acid 12 meadowfoam oil 8, 80 lactones 85, 230 medium chain triglycerides 56, 213, 224 lamenallenic acid 11 melting behaviour 101 Lanza process 95 melting point 5, 93, 130, 132, 138 62,63,71,72,97, 174 menhaden oil 72, 74, 174 5, 25 mercury acetate 195 lauric oils 66, 73, 78 metal working fluids 239 LDL (low density lipoprotein) 225 metathesis 197 lecithin 90 methanolysis 208, 209 Lesquerella fondleri 81 methoxy mercuriacetates 196 lesquerolic acid 13, 14, 81 methyl dihomo-y-linolenate 30 leukotrienes 184 methyl esters 208, 241 licanic acid 10 use as solvent 241 5, 6 methyl y-linolenate 30 Umnanthes alba 8, 80 methylsterols 84 Lindlar's catalyst 31 'methyl terrace' 135 linola oil 80 methylmalonate 24 , and ester 8, 9, 28, 29, 73, MGDG, see monogalactosyldiacylglycerols 80,158, 169 milk fat 62, 71, 73, 229-232 a-linolenic acid, and ester 8,9,28, 158, minor components in oils and fats 82 170 molozonide 190 y-linolenic acid, and ester 8, 9, 28-30, monkey nut oil 67 65, 161, 208 mono-acid triacylglyerols 62, 63, 68, 69 long spacings 135 Unum usitatissimum 68 melting point 135 lipase 38 monoacylglycerols 37, 120, 210, 234, 235 absorption 224 crystal structure 135 lipid analysis 104 derivatives 235 lipid classes 105, 106 synthesis 49, 55 lipid consumption 62, 226, 227 monoene acids 6, 27 lipid digestion 224 melting point 132 lipid transport 224 n-9 family 27 lipids, definition of 1, 35 monogalactosyldiacylglycerols 36, 39 Lipofrac process 95 monoglycerides, see monoacylglycerols lipolysis 38, 120,207,224 Mucor javanicus 97, 213 lipoproteins 224, 225 Mucor miehei 97, 98, 208, 213 lipoxygenase 182, 183 mustard seed oil 67, 79 Lipozyme 208 mutton tallow 72 long spacings, in long-chain compound 5 unitcell 129 myrtle 178 Lophira alata 6 Lophira procera 6 near infrared spectroscopy 138 low resolution nmr spectroscopy 140 Nephelium lappaceum 6 lubricants 239 7, 8 Lunaria biennis 8, 79 neutral lipids 35, 107 neutralisation of a crude oil 89,90 67, 78 nickel catalyst 94 maize oil 66 nicotinic ester 154 INDEX 249

Niemann-Pick disease 44 ozonides 23, 191 nitrile 219, 220 ozonisation 191 nitrogen-containing compounds 201,219 ozonolysis 190, 192 nmr spectroscopy l3C 143, 146-148, 188 PA, see phosphatidic acids lH 129, 140, 142, 143, 188 packet (stick) margarine 233 nomenclature, of fatty acids 1 PAF, see platelet-activating factor non-ionic surfactants 205, 237 palm fruit 88 nylons 240 63 palm mid-fraction 96 oats 178 palm oil 62, 63, 64, 68, 69, 75, 78, 120, octadecanoic acid 5 126, 174 octadecatetraenoic acids 10 tocols 85 octadecatrienoic acids 10 palm olein 69,95 octadecenoic acids 6, 7 palm stearin 69, 95 melting points 131 palm sterols 84 synthesis 30 5, 73 octadecynoic acids, melting point of 131 6, 7 octanoic acid 5 palm kernel oil 62, 63, 66, 68, 88, 174 octanol 14 glycerol esters 114 octanone 14 paper making 239 odd acids, polymorphism 132 parinaric acid 10 Oenothera biennis 65 partial hydrogenation 22, 159 Oenothera lamarkiana 65 passionflower oil 67 oil PC, see phosphatidylcholines content of plant sources 88, 100 PE, see phosphatidylethanolamines usage 63, 241 67, 174 yield 64 oil 67 oil-bearing trees 61 pentaerythritol esters 240 oilfield chemicals 240 peracids, see peroxy acids, and esters oilseed crops 77 peroxide value 103, 104 Olea europea 68 peroxy acids, and esters 186, 215, 216 oleic acid, and ester 6,7,28,69,73, 157, peroxyacetic acid 186 167 peroxyformic acid 186 oleic oils 78 7,27,69,78,79,146 oleins 95 PG, see phosphatidylglycerols and also oleochemicals, annual production 230 propyl gallate oleodibehenin 55, 137 phenolic antioxidants 178 Olestra 57,214 phosphatidic acids 36, 39, 41 62,63,68,69,74,75,79,88,120, synthesis 59 174 phosphatidylcholine, preparation 59 triacylglycerol composition 117 phosphatidylcholines 36,40,41,81-83, Omnium oxidative stability instrument 122 104 phosphatidylethanolamines 36,40,41, oncobic acid 14 81-83 orange roughy oil 84 phosphatidylglycerols 36, 40 Oryza sativa 69 phosphatidylinositols 36, 40, 81, 83 ox tallow 120, 124 phosphatidylserines 36, 40 oxidation 103, 162 phosphoglycerides 36, 39 biological 180, 181 phospholipases 40, 41 oxidative deterioration 103 phospholipids oxidative fission 189 analysis 117 oxidative stability 103 sources, and composition 81 oxidised fats 166 synthesis 57, 58 oxophytodienic acid 182 phosphonic acid 40 oxosphinganine 46 phosphoric acid 179 oxygenated acids 13 photo-oxygenation 162, 164, 167 oxymercuration 195 physical refining 89, 90 250 INDEX phytanic acid 12 refining 88, 89 phytol-based acids 12 regiospecific enzymes 212 phytosphingosine 44 Rf values 107 PI, see phosphatidylinositides Rhizomucor miehei 207 picolinyl alcohol 151 Rhizopus arrhizus 97, 213 picolinyl esters 151, 152 Rhizopus delemar 97, 213 picolinyl oleate 152 Rhizopus niveus 97, 213 pig fat 120, 124 Ribes niger 65 10 62, 69 67 rice bran wax 84 plasticisers 188 ricinoleic acid 13, 14,69 platelet-activating factor 42 Ricinus communis 65 polar lipids 35, 107 Ritter reaction 203 polyamides 200 rosemary 178, 179 polyene acids 8, 10, 27 rosmaric acid 179 melting point 132 polyenes oil 69,70,79,88,147, 174 n-3 family 29 triacylglycerol composition 17 n-6 family 29 sage 178 polyethoxylated fatty acids 238 sal fat 66 polyethyleneoxide amines 238 salad oils 234 polyglycerol esters 236 Salatrim 56 polymethyl branched acids 12 salmon phosphatidylcholines 122 polymorphism 129, 137, 138,287 Salva nilotica 180, 181 polyoxyethylene esters 222 sampling 100 polyurethanes 188 sand eel 72 poppy seed oil 120 santalbic acid 11 primrose oil, see evening primrose oil Sapium sebiferum seed oil 39 pristanic acid 12 saponification 207 production (annual), oils and fats 61 saponification equivalent 102 production, of major oils 63 sapomification value 102 propanediol esters 43 sardine oil 72, 74 propionate 24 saturated acids 4 propyl gallate 177 Schleichera trifuga 6 propylene glycol 236 sebacic acid 14 prostacyclin 184 selacholeic acid 7 prostaglandins 29, 184 selectivity factors 92 protecting groups 48, 49 63,67,69,70,88, 174, 178, PS, see phosphatidylserines 179 Pseudomonas sp. 210 sesamol 178, 179 psychosine 46 Sesamum indicum 70 pumpkin oil 67 66 Punica granatum 10 sheep tallow 120 10 Shorea robusta 66 pyrulic acid 11 Shorea stenoptera 66 short spacings, in long-chained compound quaternary ammonium compounds 219, unit cell 129 220,237 short-chain compounds 168 silica 90 Raman spectra 138 silver ion chromatography 18, 111, 118 rambutan tallow 6 hplc 119 Rancimat 103, 104 silver ion systems 116 random distribution 211 Simmondsia chinensis 8 randomisatioo 96 single low oil 68 rapeseed oil 62,63,68,69,76,78, 82, 84, sitosterol 84 88, 120, 124, 127 slip melting point 101 tocols 85 sn, see stereospecifically numbered rat liver phosphatidylcholines 122 soft (tub) margarine 233 INDEX 251 solid fat content 102, 141 synlubes 240 solid fat index 102 synthesis solvent crystallisation 95 fatty acids 45 sorbitan esters 236 lipids 45 sorbitan tristearate 234 systematic names 62,63,69,70,76,82,88,124, 174 tall oil 62, 69, 71, 78, 200 tocols 85 tallow 62,63,71,78, 126, 174 triacylglycerol composition 117 triacylglycerol composition 117 soybean sterols 84 tallow-grease 63 speciality oils 66, 67 tandem mass spectrometry 149, 153 sperm 84 tariric acid 10, 11 sphinganine 46 TBA test 103 sphingenine 44,45, 47 TBHQ, see tertbutyl hydroquinone biosynthesis 46 TeL (triple chain length) structures 133, sphingolipidoses 44 136 sphingolipids 43, 44 tea 178 sphingomyelin 44, 47 tertbutyl hydroquinone 177 biosynthesis 47 tetracosanoic acid 5 sphingosine 36, 44 tetracosenoic acid 7ยท spreading fats 233 tetradecanoic acid 5 squalene 82, 83 tetrahydroxystearic acid 189 stabilisers 188 tetramethylalkanoic acids 12 Staphylococcus aureus 97, 213 textiles 239 steam deodorisation 196 Theobroma cacao 65,66 steam refining 90 thin-layer chromatography (tic) 18, 19, 5 108 8, 29 thiobarbituric acid test 104 stearins 95 three-quarter fat butter 232 stearolic acid 11 three-quarter fat margarine 232 sterculic acid 13, 181 threshold flavour values 166 stereomutation 90, 92, 196 thomboxane 184 stereospecific analysis 122-127 thyme 178 stereospecific processes 118 titre 101 stereospecifically numbered 35 tocols 83-85, 174, 178 sterol esters 36, 85 tocopherols 82-85,174,178 sterols 82, 84 tocotrienols 82-85, 174, 178 stick (packet) margarine 233 trans-acids 11, 102,225,229,232 stigmasterol 84 triacylglycerols 36, 37 stillingia oil 39 composition 74, 75, 76, 111, 114, 117 Stokes aster 15, 81 synthesis 52, 55 Strophanthus seed oils 13 trifluoroacetates 106 structured lipids 54 triglycerides, see triacylglycerols suberins 43 trihydroxymethylpropane esters 240 sucrose polyester 214,225 trilaurin 134 sugar cane wax 84 trimethylalkanoic acids 12 sugar esters 36 trimethylsilyl ethers 106 sulphate 217 triolein, hydrogenation 93 sulphonation 220 triterpenoid alcohols 85 sulphur-containing compounds 202 tub margarine 233 62, 63, 69, 70, 79, 82, 88, tuna 74 174 tung oil 10, 62 sterols 84 tocols 84 ultraviolet spectroscopy 137 Sunola 71 undecenoic acid 14 super refining 90 unit cell 130 surface-active agents 237 unsaponifiable fraction 103 surfactants 209, 234, 237 unsaturation 102 252 INDEX

urea crystallisation 17 67, 174 urethanes 123 tocols 85 urofuranic acids 16 wax esters 36, 116 waxes 84 7, 230 wheatgerm oil 67, 174 vegetable oils 69 tocols 85 vernolic acid 15, 81, 188 Wightia seed oils l3 Vernonia galamensis 81 Wijs' reagent 102 Vernonia sp. 15 winterisation 96 visible fat 223 Wittig reaction 31 vitamin A 82 wool wax 84 vitamin C 179 vitamin D 82 X-ray diffraction 129 vitamin E 82, 84, 85, 175 ximenynic acid 10, 11 vitamin K 82 VLDL (very low density lipoprotein) 225 Zea mays 66 von Rudloff oxidation 190 zoomaric acid 6,7