Food Lipids: Chemistry, Nutrition, and Biotechnology

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173. W.-C. Song and A. R. Brash. Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450. Science 253:781 (1991). 174. T. D. Simpson and H. W. Gardner. Allene oxide synthase and allene oxide cyclase, enzymes of the jasmonic acid pathway, localized in Glycine max tissues. Plant Physiol. 108:199 (1995). 175. H. W. Gardner. Lipoxygenase pathway in cereals. In: Advances in Cereal Science and Technology (Y. Poneranz, ed.). American Association of Cereal Chemists, St. Paul, MN, 1988, p. 161. 176. B. A. Vick and D. C. Zimmerman. Pathways of fatty acid hydroperoxide metabolism in spinach leaf chloroplasts. Plant Physiol. 85:1073 (1987). 177. J. J. Sanchez-Serrano and J. Leon. Molecular biology of jasmonic acid biosynthesis in plants. Plant Physiol. Biochem. 37:373 (1999). 178. P. Reymond, H. Weber, M. Damond, and E. E. Farmer. Differential gene expression in response to mechanical wounding and insect feeding in Arabidopsis. Plant Cell. 12:707 (2000). 179. M. Hayashi, K. Toriyama, M. Kondo, and M. Nishimura. 2,4-Dichlorophenoxybutyric acid-resistant mutants of Arabidopsis have defects in glyoxysomal fatty acid �-oxidation. Plant Cell. 10:183 (1998). 180. P. Feng and D. C. Zimmerman. Substrate specificity of flax hydroperoxide isomerase. Lipids 14:170 (1979). 181. B. A. Vick and D. C. Zimmerman. Lipoxygenase, hydroperoxide isomerase, and hydroperoxide cyclase in young cotton seedlings. Plant Physiol. 67:92 (1981). 182. W.-C. Song, C. D. Funk, and A. R. Brash. Molecular cloning of an allene oxide synthase: A cytochrome P-450 specialized for the metabolism of fatty acid hydroperoxides. Proc. Natl. Acad. Sci. U.S.A. 90:8519 (1993). 183. J. M. Anderson. Membrane-derived fatty acids as precursors to second messengers. In: Second Messengers in Plant Growth and Development (W. F. Boss and D. J. Morre, eds.) Alan R. Liss, New York, 1989, p. 181. 184. R. A. Weidhase, H. Kramell, J. Lehmann, H. Liebisch, W. Lerbs, and B. Parthier. Methyl jasmonate-induced changes in the polypeptide pattern of senescing barley leaf segments. Plant Sci. 51:177 (1987). 185. H. S. Mason and J. E. Mullet. Expression of two soybean vegetative storage protein genes during development and in response to water deficit, wounding and jasmonic acid. Plant Cell 2:569 (1990). 186. P. E. Staswick, J.-F. Huang, and Y. Rhee. Nitrogen and methyl jasmonate induction of soybean vegetative storage protein genes. Plant Physiol. 96:130 (1991). 187. E. Bell, R. A. Creelman, and J. E. Mullet. A chloroplast lipoxygenase is required for wound-induced jasmonic acid accumulation in Arabidopsis. Proc. Natl. Acad. Sci. U.S.A. 92:8675 (1995). 188. E. Falkenstein, B. Groth, A. Mithofer, and E. W. Weiler. Methyljasmonate and �linolenic acid are potent inducers of tendril coiling. Planta 185:316 (1991). 189. H. Gundlach, M. J. Muller, T. M. Kutchan, and M. H. Zenk. Jasmonic acid is signal transducer in elicitor-induced plant cell cultures. Proc. Natl. Acad. Sci. U.S.A. 89:2389 (1992). 190. E. E. Farmer, R. R Johnson, and C. A. Ryan. Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic acid. Plant Physiol. 98:995 (1992). 191. E. E. Farmer and C. A. Ryan. Interplant communication: Airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc. Natl. Acad. Sci. U.S.A. 87:7713 (1990). 192. H. Pena-Cortes, T. Albrecht, S. Prat, E. W. Weiler, and L. Willmitzer. Aspirin prevents wound-induced gene expression in tomato leaves by blocking jasmonic acid biosynthesis. Planta 191:123 (1993). Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.
193. B. A. Stelmach, A. Müller, P. Hennig, D. Laudert, L. Andert, and E. W. Weiler. Quantitation of the octadecanoid 12-oxophytodienoic acid, a signaling compound in plant mechanotransduction. Phytochemistry 47:539 (1998). 194. S. Blechert, C. Bockelmann, M. Füsslein, T. Schrader, B. Stelmach, U. Niesel, and E. W. Weiler. Structure–activity analyses reveal the existence of two separate groups of active octadecanoids in elicitation of the tendril-coiling response of Bryonia dioica Jacq. Planta 207:470 (1999). 195. S. Blechert, W. Brodschelm, S. Holder, L. Kammerer, T. M. Kutchan, M. J. Mueller, Z. Xia, and M. H. Zenk. The octadecanoic pathway: Signal molecules for the regulation of secondary pathways. PNAS. 92:4099 (1995). 196. R. Kramell, O. Miersch, R. Atzorn, B. Parthier, and C. Wasternack. Octadecanoidderived alteration of gene expression and the ‘‘oxylipin signature’’ in stressed barley leaves. Implications for different signaling pathways. Plant Physiol. 123:177 (2000). 197. H. Weber, B. A. Vick, and E. E. Farmer. Dinor-oxophytodienoic acid: A new hexadecanoid signal in the jasmonate family. Proc. Natl. Acad. Sci. U.S.A. 94:10473 (1997). 198. T. Koch, T. Krumm, V. Jung, J. Engelberth, and W. Boland. Differential induction of plant volatile biosynthesis in the lima bean by early and late intermediates of the octadecanoid-signaling pathway. Plant Physiol. 121:153 (1999). 199. H. W. Gardner. Biological roles and biochemistry of the lipoxygenase pathway. HortScience 30:197 (1995). 200. S. Avdiushko, K. P. C. Croft, G. C. Brown, D. M. Jackson, T. R. Hamilton-Kemp, and D. F. Hildebrand. Effect of volatile methyl jasmonate on the oxylipin pathway in tobacco, cucumber and Arabidopsis. Plant Physiol. 109:1227 (1995). 201. H. Zhuang, D. F. Hildebrand, and M. M. Barth. Evidence that methyl jasmonate induces senescence of broccoli buds through stimulation of lipid peroxidation. Presentation at the National Plant Lipid Cooperative Meetings, South Lake Tahoe, CA, 1995. 202. H. Zhuang, D. F. Hildebrand, and M. M. Barth. Methyl jasmonate influence on quality, physiology and volatile formation in broccoli florets. Presentation at the IFT Annual Meeting, New Orleans, 1996. 203. T. Matoba, A. Sakurai, N. Taninoki, T. Saitoh, F. Kariya, M. Kuwahata, N. Yukawa, S. Fujino, and K. Hasfgawa. n-Hexanol formation from n-hexanal by enzyme action in soybean extracts. J. Food Sci. 54:1607 (1989). 204. D. F. Hildebrand, H. Zhuang, T. R. Hamilton-Kemp, and R. A. Anderson. C 6-aldehydes in plant leaves and preliminary information on the in vivo control of their formation. In: Handbook of Plant and Crop Physiology (M. Pessarakli, ed.). Dekker, New York, 1995, p. 313. 205. H. W. Gardner and M. Hamberg. Oxygenation of 3(Z)-nonenal to (2E)-4-hydroxy-2nonenal in the broad bean (Vicia faba L.). J. Biol. Chem. 268:6971 (1993). 206. K. A. Hudak and J. E. Thompson. Subcellular localization of secondary lipid metabolites including fragrance volatiles in carnation petals. Plant Physiol. 114:705 (1997). 207. D. D. Rowan, J. M. Allen, S. Fielder, and M. B. Hunt. Biosynthesis of straight-chain ester volatiles in Red Delicious and Granny Smith apples using deuterium-labeled precursor. J. Agric. Food Chem. 47:2553 (1999). 208. D. F. Hildebrand, T. R. Hamilton-Kemp, J. H. Loughrin, K. Ali, and R. A. Andersen. Lipoxygenase 3 reduces hexanal production from soybean seed homogenates. J. Agric. Food Chem. 39:1357 (1990). 209. H. Zhuang, R. A. Andersen, T. R. Hamilton-Kemp, and D. F. Hildebrand. The impact of alteration of polyunsaturated fatty acid levels on C 6-aldehyde formation of Arabidopsis thaliana leaves. Plant Physiol. 111:805 (1996). Copyright 2002 by Marcel Dekker, Inc. All Rights Reserved.
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TM Food Lipids Chemistry, Nutrition
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FOOD SCIENCE AND TECHNOLOGY A Serie
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37. Omega-3 Fatty Acids in Health a
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90. Dairy Technology: Principles of
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Preface to the Second Edition Reade
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Preface to the First Edition There
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Contents Preface to the Second Edit
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20. Dietary Fats and Coronary Heart
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J. Bruce German Department of Food
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1 Nomenclature and Classification o
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described as 2-methyl-3-phytyl-1,4-
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Table 3 A Summary of Sequence Prior
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Table 5 Systematic, Common, and Sho
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saturation of EFA occurs (primarily
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Figure 5 Prostaglandin metabolites
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Figure 7 Prostanoic acid and prosta
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Figure 9 Eicosenoid isomers in part
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Figure 10 Nomenclature of cyclic fa
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Figure 13 Hydroxy fatty acid struct
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Figure 15 Furanoid fatty acid struc
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Table 7 Short Abbreviations for Som
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Figure 20 Steroid nomenclature. rep
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Figure 22 Cholesterol oxidation pro
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E. Phosphoglycerides (Phospholipids
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Figure 26 Glyceroglycolipid structu
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Figure 28 Structures of some vitami
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6. IUPAC. Nomenclature of Organic C
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2 Chemistry and Function of Phospho
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variant [1]. Phosphonolipids are ma
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nonelectrolytes, however, the perme
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pensations in that enthalpy lost by
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Table 3 Membrane Deterioration in A
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erols to generate semisolid or plas
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The interaction of phospholipids wi
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fatty acid occurs when Fe 3� at t
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4. M. C. Blok, L. L. M. van Deenen,
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47. N. Markova, E. Sparr, L. Wadso,
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87. R. J. Hsieh. Contribution of li
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3 Lipid-Based Emulsions and Emulsif
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may be composed of surface-active c
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2. Cloud Point When a surfactant so
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HLB=7� � (hydrophilic group num
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sion is known as the phase inversio
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strongly with each other rather tha
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� = � (1 � 2.5�) (3) 0 wher
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Figure 8 Biopolymer molecules or ag
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divide homogenization into two cate
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2� �P 1 = (4) r where � is th
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flow rate, decreasing the size of t
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sion be particularly small, it is u
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2. Electrostatic Interactions Elect
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profile of interdroplet pair potent
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Figure 12 Mechanisms of emulsion in
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[Eq. (9)], but at high droplet conc
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alteration in the system’s compos
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Food emulsions always contain dropl
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creaming and sedimentation in emuls
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Foams (E. Dickinson and G. Stainsby
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4 The Chemistry of Waxes and Sterol
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Shrinkage and flash point are two f
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lowing discussion on chemical analy
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violet chromophore. Application of
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Figure 1 Examples of naturally occu
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Scheme 1 Synthesis of mevalonic aci
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Scheme 3 Synthesis of farnesyl pyro
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Scheme 6 Biosynthesis of cholestero
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educe the risk of coronary heart di
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of cholesterol to bile acids (Schem
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Scheme 10 Metabolic alterations of
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sample preparation is usually emplo
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at levels of 1-100 �g per compone
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30. H. W. Chen, A. A. Kandutsch, an
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Biologically Significant Steroids (
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5 Extraction and Analysis of Lipids
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preparing nutritional labeling mate
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polar solvents, such as alkanols, f
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a ternary system consisting of chlo
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lipids from meat or hydrolytic prod
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perature under vacuum. Acid hydroly
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IV. ANALYSIS OF LIPID EXTRACTS Lipi
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ments, etc.) primarily involves chr
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2. Gas Chromatography The GC (or GL
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4. Supercritical Fluid Chromatograp
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Table 3 Solvent Systems that Could
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sibility of determining all compone
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the isolated trans band is another
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ionized molecule has the highest m/
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3. W. R. Bloor. Outline of a classi
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45. Association of Official Analyti
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90. M. N. Vaghela and A. Kilara. A
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132. C. G. Walton, W. M. N. Ratnaya
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6 Methods for trans Fatty Acid Anal
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where A = abc (1) 1 A = absorbance
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methyl elaidate weight equivalents
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method was modified by inclusion of
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may be packed or bound to a column,
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Figure 4 The C-18 region of the gas
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Table 2 Response Factors of Unsatur
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Figure 5 Separation of the phenacyl
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B. Gas Chromatography/IR Spectrosco
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Figure 7 Expanded IR spectral range
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CFAMs before converting them to the
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Figure 8 GC-EIMS chromatographic da
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flame ionization detection. The fat
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levels in excess of 50% of the tota
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22. A. Huang and D. Firestone. Dete
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59. E. G. Perkins and C. Smick. Oct
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97. Association of Official Analyti
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136. J. J. Myer and A. Kukis. Elect
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7 Chemistry of Frying Oils KATHLEEN
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Table 1 Effects of Physical and Che
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Figure 3 Oxidation reactions in fry
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or intermittent frying, oil filtrat
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for the ultimate criteria to evalua
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triacylglycerol polymers, and triac
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100 compounds identified in hydroge
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5. J. Pokorny. Flavor chemistry of
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50. Anonymous. Recommendations of t
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8 Recovery, Refining, Converting, a
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Figure 1 Depiction of hard screw pr
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Figure 2 Depiction of prepress solv
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Seed containing more than the criti
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Figure 5 Steps in processing soybea
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specification of 50% protein is met
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tent of prepress cake is 15-18%, an
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in successive passes through the be
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Figure 10 Additional commonly used
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that follow the DT. Drying at norma
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B. Extraction of Oil-Bearing Fruits
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1. Wet Rendering Wet rendering is t
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Figure 15 Process flow sheet for de
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Table 2 Properties of Some Crude an
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Figure 16 Process flow sheet for al
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Figure 17 Process flow sheet for va
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for problematic high wax contents (
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Figure 19 Oil processing facilities
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Figure 20 Depiction of physical ref
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4-7�C, and then to tanks with slo
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Figure 21 Hydrogenation reaction me
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ond, which may form in its original
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Figure 24 Plasticization of margari
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Figure 25 Equipment used in expande
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selectivity, others claim success i
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48. E. J. Campbell. Sunflower oil.
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9 Crystallization and Polymorphism
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Generally, it is accepted that both
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Figure 2 A point lattice. (Adapted
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structure.... The term ‘fat’ us
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Figure 6 Schematic representation o
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Figure 8 Polymorphic transitions of
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where A = B = C and all are saturat
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LMF was found to facilitate the tra
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Table 3 Nomenclature and Melting Po
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Other mixed-fat systems have been s
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Figure 12 Proposed intermediate str
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17. K. Larsson. The crystal structu
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59. G. G. Jewell. Vegetable fats. I
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10 Chemical Interesterification of
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however, since monoacylglycerols an
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D. The ‘‘Real’’ Catalyst Th
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Figure 3 Proposed reaction mechanis
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Figure 5 Kinetics of interesterific
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Table 1 Theoretical Triacylglycerol
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Cast et al. [55] demonstrated the r
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Solid: Liquid: SSS, 33.3% OOO, 8.3%
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Figure 11 Changes in the fatty acid
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fication and blending on butterfat-
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influence of interesterification on
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B. Margarines In the manufacture of
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Figure 16 Proportion of soild fat o
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Tautorus and McCurdy [102] demonstr
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ACKNOWLEDGMENTS The authors acknowl
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54. A. Kuksis, M. J. McCarthy, and
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101. S. Zalewski and A. M. Gaddis.
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11 Lipid Oxidation of Edible Oil DA
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Figure 1 Molecular orbital of tripl
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Figure 3 Singlet oxygen formation b
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tween substrate and triplet oxygen
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Figure 8 Conjugated and nonconjugat
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Figure 11 Conjugated hydroperoxide
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etween the oxygen and the oxygen of
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cadienal, trans,trans-2,4-decadiena
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Figure 14 Mechanism for the formati
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Copyright 2002 by Marcel Dekker, In
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Figure 18 Formation and reactions o
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Figure 19 Effect of 0, 0.25, 0.5, a
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Figure 21 Singlet oxygen quenching
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10. E. N. Frankel. Chemistry of aut
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52. A. L. Callison. Singlet oxygen
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12 Lipid Oxidation of Muscle Foods
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A. Initiation The direct reaction o
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undles), and endomysia (sheaths of
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sosomes, etc. A comparison of the l
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dative stability, comparisons betwe
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5. Hydrolysis of Lipids and Associa
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of iron from the heme pocket by coo
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Membrane systems that reduce iron c
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phases of storage [51,187,188]. In
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4. Glutathione While the traditiona
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G. Mathematical Modeling The pathwa
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with this chemical, treated salmon
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multicomponent alternatives [304,30
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and its extent was related to inten
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esponded similarly to vacuum packag
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31. M. L. Greaser, R. G. Cassens, W
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72. J. S. Elmore, D. S. Mottram, M.
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112. J. Kanner, H. Mendel, and P. B
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154. M. B. Korycka-Dahl and T. Rich
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193. P. Akhtar, J. I. Gray, T. H. C
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230. B. Bjerkeng and G. Johnsen. Fr
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271. C.-J. Huang, and M.-L. Fwu. De
Page 427 and 428: 313. M. G. Mast and J. H. MacNeil.
Page 429 and 430: 353. H. A. Ghanbari, W. B. Wheeler,
Page 431 and 432: 13 Fatty Acid Oxidation in Plant Ti
Page 433 and 434: 1. Fatty Acid Activation Prior to d
Page 435 and 436: L.) leaf peroxisomes exhibits highe
Page 437 and 438: Figure 2 The glyoxylate cycle in gl
Page 439 and 440: C. �-Oxidation of Specific Fatty
Page 441 and 442: cotyledons and partially purified.
Page 443 and 444: Catabolism of heptanoyl CoA as well
Page 445 and 446: Figure 6 Peroxisome catabolism of m
Page 447 and 448: onstrated that �-oxidations requi
Page 449 and 450: that the member of the enzyme famil
Page 451 and 452: Plant oxylipin pathway, also named
Page 453 and 454: Figure 9 Proposed scheme for lipoxy
Page 455 and 456: oleic acid. These results suggest t
Page 457 and 458: of the seed pod reversed senescnece
Page 459 and 460: Figure 11 ‘‘Heterolytic’’-t
Page 461 and 462: Since 1971, when this physiologic r
Page 463 and 464: Table 1 Physiological Effects of Ja
Page 465 and 466: erides, although PUFAs in both form
Page 467 and 468: 9-hydroperoxides and did not attack
Page 469 and 470: aerial parts of plants, constitutes
Page 471 and 472: 32. J. B. Ohlrogge and V. S. Eccles
Page 473 and 474: 74. L. J. Morris. The mechanism of
Page 475 and 476: 115. B. A. Vick. Oxygenated fatty a
Page 477: 153. T. K. Peterman and J. N. Siedo
Page 481 and 482: 230. M. Hamberg, C. A. Herman, and
Page 483 and 484: 14 Methods for Measuring Oxidative
Page 485 and 486: ated fatty acids during oxidation (
Page 487 and 488: Several other chemical methods have
Page 489 and 490: Figure 3 Relationship between perox
Page 491 and 492: distillate. In case of the distilla
Page 493 and 494: and ketones. This ion is formed fro
Page 495 and 496: (Fig. 9), foaming, color, viscosity
Page 497 and 498: Yen and Duh [69] and Chen and Ho [7
Page 499 and 500: Figure 10 1 H Nuclear magnetic reso
Page 501 and 502: to Marquez-Ruiz et al. [93], who us
Page 503 and 504: 35. F. Shahidi, J. Yun, L.J. Rubin,
Page 505 and 506: 77. H. Saito and K. Nakamura. Appli
Page 507 and 508: 15 Antioxidants DAVID W. REISCHE Th
Page 509 and 510: Hydroperoxide degradation leads to
Page 511 and 512: e cyclical, with regeneration of th
Page 513 and 514: A. Synthetic Antioxidants Synthetic
Page 515 and 516: Propyl gallate (PG) 212.20 White cr
Page 517 and 518: 4. 6-Ethoxy-1,2-dihydro-2,2,4-trime
Page 519 and 520: Figure 3 Structures of tocopherols
Page 521 and 522: Figure 4 Structures of ascorbic aci
Page 523 and 524: 4. Enzymatic Antioxidants Glucose o
Page 525 and 526: would be imprudent to discount any
Page 527 and 528: droxycoumarin (scopoletin), and hyd
Page 529 and 530:
Figure 7 Structures of sesame antio
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8. G. Minotti. Sources and role of
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50. K. Shimada, H. Muta, Y. Nakamur
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16 Antioxidant Mechanisms ERIC A. D
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For instance, the hydrogen of the h
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Figure 2 Mechanism by which one phe
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Figure 4 Formation of �-tocophero
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Figure 6 Formation of an epoxyquino
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gallate. The antioxidant mechanism
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Figure 8 Products formed from the o
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in food systems, transition metals
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An intersystem energy transfer occu
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V. ALTERATIONS IN LIPID OXIDATION B
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VII. ANTIOXIDANT INTERACTIONS Biolo
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26. J. Kanner, J. B. German, and J.
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68. J. Kanner, F. Sofer, S. Harel,
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17 Fats and Oils in Human Health DA
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Table 1 Classification of LDL Parti
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stearic) had been incorporated by i
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studies contains equal amounts (40-
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Table 5 Influence of 25% Caloric Re
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26. L. D. Cowan, D. L. O’Connell,
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fatty acid margarine on serum lipid
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nutrition examination survey. I. Ep
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18 Unsaturated Fatty Acids STEVEN M
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Figure 1 A generalized scheme for h
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Plant fatty acids provide a seminal
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plants [27]. However, the requireme
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The reciprocal response of the �6
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fatty acids and a dynamic system fo
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production of commercially viable o
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acids synthesized de novo, primaril
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Figure 4 The cis and trans configur
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VI. SYNTHESIS AND ABUNDANCE OF PUFA
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of eicosanoids. It is present in al
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usual NMIFA structures with potenti
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10. S. P. Baykousheva, D. L. Luthri
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47. M. J. T. Alaniz, I. N. T. d. Go
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86. R. J. Henderson and D. R. Toche
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19 Dietary Fats, Eicosanoids, and t
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synthesize EPA from linolenic acid
Page 611 and 612:
Figure 2 Immune responses as a func
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done predominantly in rodent specie
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guinea pigs showed increased immune
Page 617 and 618:
of energy from fat. Feeding the low
Page 619 and 620:
14. P. Purasiri, A. Murray, S. Rich
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20 Dietary Fats and Coronary Heart
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(HDLs). Each class has its own char
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70% of the total amount of choleste
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McGandy and coworkers [8] have care
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Figure 4 Effects of myristic and pa
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3. Polyunsaturated Fatty Acids Poly
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Figure 8 Effects of a mixture of sa
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chemoattractant protein-1 (MCP-1),
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Figure 11 In vitro LDL oxidation. F
Page 639 and 640:
Table 4 Fatty Acid Composition of a
Page 641 and 642:
Figure 12 Processes involved in thr
Page 643 and 644:
as compared with a diet rich in but
Page 645 and 646:
from cardiovascular disease [73,74]
Page 647 and 648:
Figure 16 Schematic representation
Page 649 and 650:
aggregation tendency induced by som
Page 651 and 652:
35. D. R. Janero. Malondialdehyde a
Page 653 and 654:
68. B. J. Burrl, R. M. Dougherty, D
Page 655 and 656:
21 Conjugated Linoleic Acids: Nutri
Page 657 and 658:
method that works optimally in all
Page 659 and 660:
adipose tissue contained two major
Page 661 and 662:
providing rats with 0.5% and 1% CLA
Page 663 and 664:
with the control group. Interesting
Page 665 and 666:
feeding. These findings suggest tha
Page 667 and 668:
In contrast to the antioxidative pr
Page 669 and 670:
esponsible, at least in part, for t
Page 671 and 672:
Yamasaki et al. studied CLA and ant
Page 673 and 674:
17. J. K. G. Kramer, P. W. Parodi,
Page 675 and 676:
55. C. Ip, S. F. Chin, J. A. Scimec
Page 677 and 678:
90. J. S. Munday, K. G. Thompson, a
Page 679 and 680:
126. J. Singh, R. Hamid, and B. S.
Page 681 and 682:
22 Dietary Fats and Obesity DOROTHY
Page 683 and 684:
For example, some have reported tha
Page 685 and 686:
the fat component and the other hal
Page 687 and 688:
shows that there is a negative corr
Page 689 and 690:
C. Influence of Dietary Fat on Fatt
Page 691 and 692:
Figure 1 Signal transduction cascad
Page 693 and 694:
mals indicate that high-fat feeding
Page 695 and 696:
processes. Numerous studies provide
Page 697 and 698:
monier (252) suggested that in cert
Page 699 and 700:
4. National Task Force on Obesity.
Page 701 and 702:
46. F. Lucas, K. Ackroff, and A. Sc
Page 703 and 704:
90. D. Mela. Sensory preference for
Page 705 and 706:
133. D. R. Romsos and G. A. Leveill
Page 707 and 708:
169. T. Ide, H. Kobayashi, L. Ashak
Page 709 and 710:
207. A. B. Awad and E. A. Zepp. Alt
Page 711 and 712:
246. Y. B. Kim, R. Nakajima, T. Mat
Page 713 and 714:
23 Lipid-Based Synthetic Fat Substi
Page 715 and 716:
operations, and in theory, can repl
Page 717 and 718:
Table 3 Types of Lipid-Based Fat Su
Page 719 and 720:
Figure 1 Structure of sucrose polye
Page 721 and 722:
Figure 3 Synthetic scheme for olest
Page 723 and 724:
Figure 5 Structure of sorbitol poly
Page 725 and 726:
Figure 8 Structure of raffinose pol
Page 727 and 728:
Figure 11 Structure of methyl galac
Page 729 and 730:
Table 4 Some Properties of Sucrose
Page 731 and 732:
Figure 15 Structure of trialkoxytri
Page 733 and 734:
Figure 19 Structure of polysiloxane
Page 735 and 736:
inversely related to the degree of
Page 737 and 738:
Table 8 Some Nutritional Uses of No
Page 739 and 740:
genetic assay in Chinese hamster ov
Page 741 and 742:
IX. PERSPECTIVES With the approval
Page 743 and 744:
30. L. Osipow, F. D. Snell, D. Marr
Page 745 and 746:
72. K. W. Miller and P. H. Long. A
Page 747 and 748:
24 Food Applications of Lipids FRAN
Page 749 and 750:
Table 3 Typical Fatty Acid Composit
Page 751 and 752:
are significant differences in oil
Page 753 and 754:
Table 6 Production and Disappearanc
Page 755 and 756:
and margarine should be pronounced
Page 757 and 758:
Table 8 Approximate Fatty Acid Comp
Page 759 and 760:
egions of the world. In addition to
Page 761 and 762:
50-55% fat. Production figures for
Page 763 and 764:
utter with up to 5% of another fat
Page 765 and 766:
market with high overrun and good s
Page 767 and 768:
11. D. Hettinga. Butter. In: Bailey
Page 769 and 770:
25 Lipid Biotechnology KUMAR D. MUK
Page 771 and 772:
Table 1 Lipid Content and Levels of
Page 773 and 774:
as 80% lipids of which about 90% ar
Page 775 and 776:
Table 6 Wax Esters Formed by Acinet
Page 777 and 778:
Some other biosurfactants include e
Page 779 and 780:
Figure 6 Microbial production of hy
Page 781 and 782:
Figure 9 Microbial production of ke
Page 783 and 784:
Figure 12 Microbial production of k
Page 785 and 786:
Table 8 Specificity of Triacylglyce
Page 787 and 788:
Figure 16 Lipase-catalyzed transest
Page 789 and 790:
Figure 20 Preparation of structured
Page 791 and 792:
Figure 24 Preparation of monoacylgl
Page 793 and 794:
Fatty acid esters of polyols are us
Page 795 and 796:
Figure 29 Specificity constants in
Page 797 and 798:
Figure 31 Preparation of concentrat
Page 799 and 800:
Figure 35 Enrichment of very long c
Page 801 and 802:
B. Phospholipases Figure 38 shows t
Page 803 and 804:
Lysophosphatidic acid has been prep
Page 805 and 806:
Figure 41 Transesterification of ph
Page 807 and 808:
Figure 46 Enzymatic production of h
Page 809 and 810:
Figure 50 Hydration of linoleic aci
Page 811 and 812:
Figure 51 Principle of enzymatic de
Page 813 and 814:
13. E. Molina Grima, J. A. Sánchez
Page 815 and 816:
53. M. Powalla, S. Lang, and V. Wra
Page 817 and 818:
96. R. Schuch and K. D. Mukherjee.
Page 819 and 820:
138. K. D. Mukherjee and I. Kiewitt
Page 821 and 822:
179. U. T. Bornscheuer, H. Stamatis
Page 823 and 824:
222. H. Stamatis, V. Sereti, and F.
Page 825 and 826:
265. S. R. Moore and G. P. McNeill.
Page 827 and 828:
303. C. Virto, I. Svensson, and P.
Page 829 and 830:
343. E. Blee and F. Schuber. Regio-
Page 831 and 832:
26 Microbial Lipases JOHN D. WEETE
Page 833 and 834:
ation. Fungal lipases typically exi
Page 835 and 836:
of buffer A containing 1 M ammonium
Page 837 and 838:
without shaking for 30 minutes, whe
Page 839 and 840:
the C domain of the protein through
Page 841 and 842:
Figure 2 (Continued) Figure 3 Schem
Page 843 and 844:
on the substrate and presence or ab
Page 845 and 846:
Table 3 Selectivities of Multiple E
Page 847 and 848:
lanuginosa, C. antarctica B, Rhizop
Page 849 and 850:
10. C. T. Hou and T. M. Johnston. S
Page 851 and 852:
53. C. C. Akoh. Enzymatic synthesis
Page 853 and 854:
94. D. M. Lawson, A. M. Brzozowski,
Page 855 and 856:
135. B. K. Yang and J. P. Chen. Gel
Page 857 and 858:
27 Enzymatic Interesterification WE
Page 859 and 860:
esterification of butterfat at 40
Page 861 and 862:
also found to decrease the crystall
Page 863 and 864:
T c than animal fats. The T c for v
Page 865 and 866:
in the oxyanion hole is the amino a
Page 867 and 868:
of the interface as a measure of su
Page 869 and 870:
Figure 11 Catalytic mechanism for l
Page 871 and 872:
Figure 13 Triacylglycerol products
Page 873 and 874:
imization of interesterification, a
Page 875 and 876:
supports include high losses of act
Page 877 and 878:
is a thin layer located directly ne
Page 879 and 880:
volume per year. The volumetric act
Page 881 and 882:
and removal of reactants and produc
Page 883 and 884:
vinyl chloride. In a membrane such
Page 885 and 886:
of the enzyme. Animal and plant lip
Page 887 and 888:
esters as surface active agents dur
Page 889 and 890:
14. P. Kalo, H. Huotari, and M. Ant
Page 891 and 892:
57. F. Pabai, S. Kermasha, and A. M
Page 893 and 894:
94. J. Kurashige. Enzymatic convers
Page 895 and 896:
28 Structured Lipids CASIMIR C. AKO
Page 897 and 898:
Figure 2 Structure of a physical mi
Page 899 and 900:
2. Medium Chain Fatty Acids and Tri
Page 901 and 902:
Figure 4 Pathway for eicosanoid bio
Page 903 and 904:
leukotrienes (hydroxy fatty acids a
Page 905 and 906:
Figure 7 Structure of Benefat (bran
Page 907 and 908:
cause of the huge capital investmen
Page 909 and 910:
Figure 8 Reaction scheme showing ac
Page 911 and 912:
alters the native conformation of t
Page 913 and 914:
Table 6 Advantages of Enzymatic App
Page 915 and 916:
Figure 13 Stereochemical configurat
Page 917 and 918:
IV. NUTRITIONAL AND MEDICAL APPLICA
Page 919 and 920:
Table 9 Factors That Affect Outlook
Page 921 and 922:
27. G. O. Burr and M. D. Burr. A ne
Page 923 and 924:
69. M. Reslow, P. Aldercreutz, and
Page 925 and 926:
113. C. J. Gollaher, E. S. Swenson,
Page 927 and 928:
29 Biosynthesis of Fatty Acids and
Page 929 and 930:
olive (Olea europea), and avocado (
Page 931 and 932:
Table 2 (Continued) Fatty acid a Sp
Page 933 and 934:
2. Basic Features The functional un
Page 935 and 936:
Hydroxy-Acyl ACP dehydrase (Crotony
Page 937 and 938:
Figure 1 Steps of fatty acid biosyn
Page 939 and 940:
The three KAS isoforms are assigned
Page 941 and 942:
chain length acyl-ACP residues, and
Page 943 and 944:
10-carbon and 14- to 16-carbon acyl
Page 945 and 946:
In developing castor seed, BC and A
Page 947 and 948:
(viz., seed, fruit) genes, and this
Page 949 and 950:
Figure 4 Fatty acid modification re
Page 951 and 952:
12-MO, the cDNA for the enzyme has
Page 953 and 954:
Table 5 Enzyme Activities Involved
Page 955 and 956:
of reactivity is also supported by
Page 957 and 958:
tems, PTAP is a likely candidate fo
Page 959 and 960:
ifying 18:1 �9 and deacylating 18
Page 961 and 962:
oils (rich in 18:3 �6,9,12), and
Page 963 and 964:
eticulum subpopulations also finds
Page 965 and 966:
CPT (DAG ↔ PC) Extensive involvem
Page 967 and 968:
available (cf. Sec. V.C.4 and Ref.
Page 969 and 970:
erol backbone of triacylglycerols c
Page 971 and 972:
14. E. Heinz. Biosynthesis of polyu
Page 973 and 974:
56. R. C. Clough, A. L. Matthis, S.
Page 975 and 976:
91. R. J. Heath and C. O. Rock. Eno
Page 977 and 978:
124. R. Schuch, F. M. Brück, M. Br
Page 979 and 980:
Kader and P. Mazliak, eds.). Kluwer
Page 981 and 982:
197. Y. Cao, K. Oo, and A. H. C. Hu
Page 983 and 984:
241. M. C. Dobarganes, G. Márquez-
Page 985 and 986:
30 Genetic Engineering of Crops Tha
Page 987 and 988:
existing genes in the host plant ge
Page 989 and 990:
It becomes the plant breeder’s jo
Page 991 and 992:
previously mentioned low-linolenic
Page 993 and 994:
develop and apply methods, evaluate
Page 995 and 996:
enzyme with high activity for placi
Page 997 and 998:
activity in the oil palm mesocarp s
Page 999 and 1000:
Figure 4 Commercial applications of
Page 1001 and 1002:
and mildness. Because the perennial
Page 1003 and 1004:
In the context of developing increa
Page 1005 and 1006:
occurs esterified at the sn-2 posit
Page 1007 and 1008:
as high as coconut or palm kernel o
Page 1009 and 1010:
systems. Key to assessing the oppor
Page 1011 and 1012:
property encouraged us to look for
Page 1013 and 1014:
mercial lauric fats based on both P
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