FOOD LIPIDS Chemistry, Nutrition, and Biotechnology ppt

CRC Press is an imprint of the Taylor & Francis Group, an informa business Boca Raton London New York FOOD LIPIDS Chemistry, Nutrition, and Biotechnology THIRD EDITION Edited by Casimir C. Akoh • David B. Min Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page i 14.2.2008 6:50am Compositor Name: VBalamugundan CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2008 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10 9 8 7 6 5 4 3 2 1 International Standard Book Number-13: 978-1-4200-4663-2 (Hardcover) This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. 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Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Food lipids : chemistry, nutrition, and biotechnology / edited by Casimir C. Akoh and David B. Min. 3rd ed. p. ; cm. Includes bibliographical references and index. ISBN-13: 978-1-4200-4663-2 (hardcover : alk. paper) ISBN-10: 1-4200-4663-2 (hardcover : alk. paper) 1. Lipids. 2. Lipids in human nutrition. 3. Lipids Biotechnology. 4. Lipids Metabolism. I. Akoh, Casimir C., 1955- II. Min, David B. [DNLM: 1. Lipids chemistry. 2. Lipids physiology. 3. Biotechnology methods. 4. Food. 5. Nutrition Physiology. QU 85 F6865 2008] I. Title. QP751.F647 2008 612’.01577 dc22 2007031989 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page ii 14.2.2008 6:50am Compositor Name: VBalamugundan Contents Preface to the Third Edition vii Editors ix Contributors xi PART I Chemistry and Properties 1. Nomenclature and Classification of Lipids 3 Sean Francis O’Keefe 2. Chemistry and Function of Phospholipids 39 Marilyn C. Erickson 3. Lipid-Based Emulsions and Emulsifiers 63 D. Julian McClements 4. Chemistry of Waxes and Sterols 99 Edward J. Parish, Shengrong Li, and Angela D. Bell 5. Extraction and Analysis of Lipids 125 Fereidoon Shahidi and P.K.J.P.D. Wanasundara 6. Methods for trans Fatty Acid Analysis 157 Magdi M. Mossoba and Richard E. McDonald 7. Chemistry of Frying Oils 189 Kathleen Warner PART II Processing 8. Recovery, Refining, Converting, and Stabilizing Edible Fats and Oils 205 Lawrence A. Johnson 9. Crystallization and Polymorph ism of Fats 245 Patrick J. Lawler and Paul S. Dimick Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page iii 14.2.2008 6:50am Compositor Name: VBalamugundan iii 10. Chemical Interesterification of Food Lipids: Theory and Practice 267 Dérick Rousseau and Alejandro G. Marangoni PART III Oxidation and Antioxidants 11. Chemistry of Lipid Oxidation 299 Hyun Jung Kim and David B. Min 12. Lipid Oxidation of Muscle Foods 321 Marilyn C. Erickson 13. Polyunsaturated Lipid Oxidation in Aqueous System 365 Kazuo Miyashita 14. Methods for Measuring Oxidative Rancidity in Fats and Oils 387 Fereidoon Shahidi and Udaya N. Wanasundara 15. Antioxidants 409 David W. Reische, Dorris A. Lillard, and Ronald R. Eitenm iller 16. Tocopherol Stability and Prooxidant Mechanisms of Oxidized Tocopherols in Lipids 435 Hyun Jung Kim and David B. Min 17. Effects and Mechanisms of Minor Compounds in Oil on Lipid Oxidation 449 Eunok Choe 18. Antioxidant Mechanisms 475 Eric A. Decker PART IV Nutrition 19. Fats and Oils in Human Health 499 David Kritchevsky 20. Unsaturated Fatty Acids 513 Steven M. Watkins and J. Bruce German 21. Dietary Fats, Eicosanoids, and the Immune System 539 David M. Klurfeld Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page iv 14.2.2008 6:50am Compositor Name: VBalamugundan iv 22. Dietary Fats and Coronary Heart Disease 551 Ronald P. Mensink and Jogchum Plat 23. Conjugated Linoleic Acids: Nutrition and Biology 579 Bruce A. Watkins and Yong Li 24. Dietary Fats and Obesi ty 601 Dorothy B. Hausman and Barbara Mullen Grossman 25. Influence of Dietary Fat on the Development of Cancer 633 Howard Perry Glauert 26. Lipid-Based Synthetic Fat Substitutes 653 Casimir C. Akoh 27. Food Applications of Lipids 683 Frank D. Gunstone PART V Biotechnology and Biochemistry 28. Lipid Biotechnology 707 Nikolaus Weber and Kumar D. Mukherjee 29. Microbial Lipases 767 John D. Weete, Oi-Ming Lai, and Casimir C. Akoh 30. Enzymatic Interesterification 807 Wendy M. Willis and Alejandro G. Marangoni 31. Structured Lipids 841 Casimir C. Akoh and Byung Hee Kim 32. Genetic Engineering of Crops That Produce Vegetable Oil 873 Vic C. Knauf and Anthony J. Del Vecchio Index 899 Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page v 14.2.2008 6:50am Compositor Name: VBalamugundan v Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page vi 14.2.2008 6:50am Compositor Name: VBalamugundan Preface to the Third Edition The first edition of Food Lipids was published in 1998 and the second edition in 2002 by Marcel Dekker, Inc. Taylor & Francis Group, LLC, acquired Marcel Dekker and the rights to publish the third edition. We firmly believe that this book has been of interest and will help those involved in lipid resear ch and instruction. Many have bought the previous editions and we thank you for your support. The need to update the information in the second edition cannot be overstated, as more data and new technologies are constantly becoming available. We have received good comments and suggestions on how to improve the second edition. The response reassured us that there was indeed a great need for a textbook suitable for teaching food lipids, nutritional aspects of lipids, and lipid chemistry courses to food science and nutrition majors. The aim of the first and second editions remains unchanged: to provide a modern, easy-to-read textbook for students and instructors. The book is also suitable for upper-level undergraduate, graduate, and postgraduate instruction. Scien- tists who have left the university and are engaged in research and development in the industry, government, or academics will find this book a useful reference. In this edition, we have expanded on lipid oxidation and antioxidants, as these continue to be topics of great interest to the modern consumer. The title of Part III has also been changed to reflect the recent interest on the importance of antioxidants and health. Again, we have made every effort to select contributors who are internationally recognized experts. We thank them for their exceptional attention to details and timely submissions of their chapters. Overall, the text has been updated with new and available information. We removed some chapters and added new ones. Chapter 2 includes a brief discussion of sphingolipids, and Chapter 31 includes one on diacylglycerols. The new additions are Chapters 13, 16, 17, and 25. Although it is not possible to cover all aspects of lipids, we feel we hav e added and covered most topics that are of interest to our readers. The book still is divided into five main parts: Chemistry and Properties; Processing; Oxidation and Antioxidants; Nutrition; and Biotechnology and Biochemistry. We are grateful to the readers and users of the previous editions and can only hope that we have improved and updated the latest edition to your satisfaction. We welcome comments on the third edition to help us continue to provide our readers with factual information on the science of lipids. Based on the comments of readers and reviewers of the past editions, we have improved the third edition—we hope, without creating new errors, which are sometimes unavoidable for a book this size and complexity. We apologize for any errors in advance and urge you to contact us if you find mistakes or have suggestions to improve the readability and comprehension of this text. Special thanks to our readers and students, and to the editorial staff of Taylor & Francis Group, LLC, for their helpful suggestions toward improving the quality of this edition. Casimir C. Akoh David B. Min Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page vii 14.2.2008 6:50am Compositor Name: VBalamugundan vii Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page viii 14.2.2008 6:50am Compositor Name: VBalamugundan Editors Casimir C. Akoh is a distinguished research professor of food science and technology and an adjunct professor of foods and nutrition at the University of Georgia, Athens. He is the coeditor of the book Carbohydrates as Fat Substitutes (Marcel Dekker, Inc.), coeditor of Healthful Lipids (AOCS Press), editor of Handbook of Functional Lipids (CRC Press), the author or coauth or of over 162 referenced SCI publications, more than 30 book chapters, and the holder of three U.S. patents. He is a fellow of the Institute of Food Technologists (2005), American Oil Chemists’ Society (2006), and the American Chemical Society (2006). He serves on the editorial boards of five journals and is a member of the Institute of Food Technologists, the American Oil Chemists’ Society, and the American Chemical Society. He has received numerous international professional awards for h is work on lipids including the 1998 IFT Samuel Cate Prescott Award, the 2003 D.W. Brooks Award, and the 2004 AOCS Stephen S. Chang Award. He received his PhD (1988) in food science from Washington State University, Pullman. He holds MS and BS degrees in biochemistry from Washington State University and the University of Nigeria, Nsukka, respectively. David B. Min’s major research objective is to improve the oxidative and flavor stability of foods by understanding and controlling the chemical mechanisms for the flavor compound formation by a combination of GC, HPLC, IR, NMR, ESR, and MS. Dr. Min’s group painstakingly, conclusively, and scientifically developed the novel chemical mechanisms for the formation of sunlight flavor in milk, reversion flavor in soybean oil, and light sensitivity of riboflavin. He is a pioneer for the formation, reaction mechanisms and kinetics, quenching mechanisms and kinetics singlet oxygen in foods. He has published 6 books and more than 200 publications. He has been scientific editor of Journal of Food Science and Journal of the American Oil Chemists’ Society and has been on the editorial board of Journal of Critical Reviews on Food Science and Nutrition, Journal of Food Quality, Food Chemistry, International News on Fats and Oils, Food Science and Biochemistry, and Marcel Dekker Publications. He has received more than 30 national and international awards including the 1995 IFT Achievement Award of Lipid and Flavor Chemistry, the 1999 Distinguished Senior Faculty Research Award, the 2001 IFT Food Chemistry Lectureship Award, the 2002 Professor of the Year Award, and the 2004 Outstanding Teaching Award. He has been an elected member of the Korean National Academy of Science, and a fellow of the Institute of Food Technologists, the American Oil Chemists’ Society, the American Institute of Chemists, and the International Academy of Food Science and Technology. Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page ix 14.2.2008 6:50am Compositor Name: VBalamugundan ix Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page x 14.2.2008 6:50am Compositor Name: VBalamugundan [...]... oil (From Sebedio, J.L and Ackman, R.G., J Am Oil Chem Soc., 60, 1986, 1983.) Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 16 21.1.2008 10:20pm Compositor Name: PJayaraj 16 Food Lipids: Chemistry, Nutrition, and Biotechnology in vegetable oils and products made from vegetable oils (infant formulas) and include 9c,12t-18:2; 9t,12c-18:2; and 9t,12t-18:2, as well... prostaglandins originating from 20:3v6, 20:4v6, and 20:5v3, respectively The structures of the 1-, 2-, and 3-prostaglandins differ Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 12 21.1.2008 10:20pm Compositor Name: PJayaraj 12 Food Lipids: Chemistry, Nutrition, and Biotechnology COOH Arachidonic acid O COOH O OOH CHO HO PGG2 COOH O MDA OH + PGD2 COOH O HO COOH O... in Figure 1.8 is more accurate Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 14 21.1.2008 10:20pm Compositor Name: PJayaraj 14 Food Lipids: Chemistry, Nutrition, and Biotechnology O O O R1 R1 R1 R2 R2 R2 PGA PGB HO PGC HO O R1 O PGD R2 R1 R1 R2 HO R2 HO PGFα PGE COOH CH3 Prostanoic acid FIGURE 1.7 Prostanoic acid and prostaglandin ring nomenclature Tariaric (6-octadecynoic... Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition 46632_C000 Final Proof page xiv 14.2.2008 6:50am Compositor Name: VBalamugundan Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 1 21.1.2008 10:20pm Compositor Name: PJayaraj Part I Chemistry and Properties Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page... Pentacontane Hexacontane Heptacontane Octacontane Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 6 21.1.2008 10:20pm Compositor Name: PJayaraj 6 Food Lipids: Chemistry, Nutrition, and Biotechnology TABLE 1.2 IUPAC Rules for Hydrocarbon Nomenclature 1 Saturated unbranched acyclic hydrocarbons are named with a numerical prefix and the termination ‘‘ane.’’ The first four in... 1,3-Diacyl-sn-glycerol OH HO O R O (αЈ) 3-Monoacyl-sn-glycerol FIGURE 1.18 Mono- and diacylglycerol structures R1 HO OH R1 O O R2 O (αЈ,β) 2,3-Diacyl-sn-glycerol O Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 22 21.1.2008 10:20pm Compositor Name: PJayaraj 22 Food Lipids: Chemistry, Nutrition, and Biotechnology TABLE 1.7 Short Abbreviations for Some Common Fatty Acids... acids and alcohols, which are the building blocks for the simple and complex lipids Simple lipids, composed of fatty acids and alcohol components, include acylglycerols, ether acylglycerols, sterols, and their esters and wax esters In general terms, simple lipids can be hydrolyzed to two different components, usually an alcohol and an acid Complex lipids include glycerophospholipids (phospholipids),... compounds The systematic, common, and shorthand designations of some saturated fatty acids are given in Table 1.4 Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 10 21.1.2008 10:20pm Compositor Name: PJayaraj 10 2 Food Lipids: Chemistry, Nutrition, and Biotechnology Unsaturated Fatty Acids By far, the most common monounsaturated fatty acid is oleic acid (18:1v9), although... -10-(2-Hexylcyclopropyl)decanoic acid Lactobacillic acid / phytomonic acid FIGURE 1.11 Nomenclature for a cyclopropenoid fatty acid Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 18 21.1.2008 10:20pm Compositor Name: PJayaraj 18 Food Lipids: Chemistry, Nutrition, and Biotechnology Cyclopropyl 10-(2-Hexylcyclopropanyl)decanoic acid (lactobacillic or phytomonic acid) CH2 COOH Cyclopropenyl... of Pure and Applied Chemists (IUPAC) and International Union of Biochemistry (IUB) collaborative efforts have resulted in comprehensive nomenclature standards [6], and the nomenclature for lipids has been reported [7–9] Only the main aspects of the Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 5 21.1.2008 10:20pm Compositor Name: PJayaraj 5 Nomenclature and Classification . York FOOD LIPIDS Chemistry, Nutrition, and Biotechnology THIRD EDITION Edited by Casimir C. Akoh • David B. Min Akoh /Food Lipids: Chemistry, Nutrition, and. Institute of Chemists, and the International Academy of Food Science and Technology. Akoh /Food Lipids: Chemistry, Nutrition, and Biotechnology, Third Edition