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F O U R T H E D I T I O N FOOD LIPIDS Chemistry, Nutrition, and Biotechnology F O U R T H E D I T I O N FOOD LIPIDS Chemistry, Nutrition, and Biotechnology Casimir C. Akoh CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2017 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 on acid-free paper Version Date: 20160725 International Standard Book Number-13: 978-1-4987-4485-0 (Hardback) This book contains information obtained from authentic and highly regarded sources. Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the valid- ity of all materials or the consequences of their use. The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint. Except as permitted under U.S. Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or uti- lized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopy- ing, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http:// www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. 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 Names: Akoh, Casimir C., date. Title: Food lipids : chemistry, nutrition, and biotechnology / [edited by] Casimir C. Akoh. Description: Fourth edition. | Boca Raton : Taylor & Francis, 2017. Identifiers: LCCN 2016030889| ISBN 9781498744850 (hardback : alk. paper) | ISBN 9781498744874 (e-book) Subjects: LCSH: Lipids. | Lipids in human nutrition. | Lipids--Biotechnology. | Lipids--Metabolism. Classification: LCC QP751 .F647 2017 | DDC 572/.57--dc23 LC record available at https://lccn.loc.gov/2016030889 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface...............................................................................................................................................ix Editor ................................................................................................................................................xi Contributors ...................................................................................................................................xiii Section i chemistry and Properties Chapter 1 Nomenclature and Classification of Lipids ..................................................................3 Sean Francis O’Keefe and Paul J. Sarnoski Chapter 2 Chemistry and Properties of Lipids and Phospholipids .............................................37 Bianca Pérez, Jingbo Li, and Zheng Guo Chapter 3 Lipid-Based Emulsions and Emulsifiers ....................................................................73 David Julian McClements Chapter 4 Chemistry of Waxes and Sterols ..............................................................................109 Edward J. Parish and Wendell S. Grainger Chapter 5 Extraction and Analysis of Lipids ............................................................................131 Fereidoon Shahidi, P. Ambigaipalan, and P.K.J.P.D. Wanasundara Chapter 6 Analysis of Fatty Acid Positional Distribution in Triacylglycerols ..........................167 Yomi Watanabe and Kazuaki Yoshinaga Chapter 7 Methods for Trans Fatty Acid Analysis ...................................................................185 Magdi M. Mossoba, Cynthia T. Srigley, Richard E. McDonald, Hormoz Azizian, and John K.G. Kramer Chapter 8 Physical Characterization of Fats and Oils ..............................................................219 Fernanda Peyronel, Edmund D. Co, and Alejandro G. Marangoni Chapter 9 Frying Oil Chemistry ...............................................................................................261 Felix Aladedunye, Usha Thiyam-Hollander, and N.A. Michael Eskin Section ii Processing and Food Applications Chapter 10 Processing and Modification Technologies for Edible Oils and Fats .......................297 Selma Türkay and Neşe Şahin-Yeşilçubuk v vi Contents Chapter 11 Crystallization Behavior of Fats: Effects of Processing Conditions ........................327 Ashwini Wagh and Silvana Martini Chapter 12 Chemical Interesterification of Food Lipids: Theory and Practice ..........................349 Dérick Rousseau, Saeed M. Ghazani, and Alejandro G. Marangoni Chapter 13 Enzymatic Purification and Enrichment of Polyunsaturated Fatty Acids and Conjugated Linoleic Acid Isomers ....................................................................381 Yuji Shimada and Toshihiro Nagao Chapter 14 Microbial Lipid Production ......................................................................................403 Ayşe Saygün, Neşe Şahin-Yeşilçubuk, Necla Aran, Yong-Ro Kim, and Suk-Hoo Yoon Chapter 15 Food Applications of Lipids .....................................................................................421 N.A. Michael Eskin and Gary R. List Chapter 16 Encapsulation Technologies for Lipids ....................................................................453 Neşe Şahin-Yeşilçubuk and Casimir C. Akoh Section iii oxidation and Antioxidants Chapter 17 Rethinking Lipid Oxidation .....................................................................................479 Karen M. Schaich Chapter 18 Polyunsaturated Lipid Oxidation in Aqueous Systems ............................................499 Kazuo Miyashita Chapter 19 Methods for Measuring Oxidative Rancidity in Fats and Oils ................................519 Fereidoon Shahidi, Jiankang Wang, and Udaya N. Wanasundara Chapter 20 Antioxidants and Their Mechanisms of Action .......................................................543 Ryan J. Elias and Eric A. Decker Chapter 21 Effects and Mechanisms of Minor Compounds in Oil on Lipid Oxidation .............567 Eunok Choe Section iV nutrition Chapter 22 Digestion, Absorption, and Metabolism of Lipids ...................................................591 Charlotte Lauridsen Contents vii Chapter 23 Omega-3 Polyunsaturated Fatty Acids and Health ..................................................603 Michelle A. Briggs, Kate J. Bowen, and Penny M. Kris-Etherton Chapter 24 Dietary Fatty Acids, Lipid Mediators, Immunity, and Inflammation ......................627 Philip C. Calder Chapter 25 Dietary Fats and Coronary Heart Disease ...............................................................639 Ronald P. Mensink and Jogchum Plat Chapter 26 Conjugated Linoleic Acid .........................................................................................667 Sun Jin Hur and Yeonhwa Park Chapter 27 Dietary Fats and Obesity ..........................................................................................689 Dorothy B. Hausman and Barbara Mullen Grossman Chapter 28 Influence of Dietary Fat on the Development of Cancer ..........................................727 Howard Perry Glauert Chapter 29 Brain Lipids in Health and Disease..........................................................................747 Jessica H. Hall and John L. Harwood Chapter 30 Biotechnologically Enriched Cereals with PUFAs in Ruminant and Chicken Nutrition ..............................................................................................765 Milan Čertík, Tatiana Klempová, Dušan Jalč, Zora Váradyová, and Slavomír Marcinčák Section V Biotechnology and Biochemistry Chapter 31 Lipid Biotechnology and Biochemistry....................................................................781 Sampson Anankanbil, Fan Suo, Peter Ruhdal Jensen, and Zheng Guo Chapter 32 Enzyme-Catalyzed Production of Lipid-Based Esters for the Food Industry: Emerging Processes and Technologies ....................................................................825 Ran Ye Chapter 33 Microbial Lipases .....................................................................................................853 Oi-Ming Lai, Eng-Tong Phuah, Yee-Ying Lee, Casimir C. Akoh, and John D. Weete Chapter 34 Enzymatic Interesterification ...................................................................................899 Wendy M. Willis, Saeed M. Ghazani, and Alejandro G. Marangoni viii Contents Chapter 35 Structured Lipids ......................................................................................................941 Casimir C. Akoh and Byung Hee Kim Chapter 36 Production of Edible Oils through Metabolic Engineering .....................................973 Randall J. Weselake, Helen K. Woodfield, Catherine J. Field, and John L. Harwood Chapter 37 Genetically Engineered Cereals for the Production of Polyunsaturated Fatty Acids ......................................................................................................997 Milan Čertík, Tatiana Klempová, Daniel Mihálik, Katarína Ondreičková, Marcela Gubišová, and Ján Kraic Index .............................................................................................................................................1011 Preface 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 and subsequent editions. I firmly believe that this book has provided those involved in lipid research and instruction with a valuable resource for materials and information. On behalf of my late former coeditor, Professor David B. Min, I thank all those who bought the previous editions and hope that you will find the fourth edition equally or more interesting and helpful. Before describing the content of the current edition, I would like to pay tribute to Professor Min, who worked very hard with me in seeing to the successful recruitment of potential authors and the publication of the previous editions. I miss him dearly and dedicate this fourth edition to his memory and his contributions to our knowledge on lipids, especially, lipid oxidation. Taylor & Francis Group and I felt the need to update the information in the third edition and include more recent topics of interest to the readers and users of this text/reference book. We continue to believe, based on the sales of the previous editions and the comments of instructors and those who purchased and used the book, that this textbook is and will continue to be suitable for teaching food lipids, nutritional aspects of lipids, and lipid chemistry/biotechnology courses to food science and nutrition majors. The aim of the first, second, third, and fourth editions remains unchanged: to provide a modern, easy-to-read textbook for students and instructors and a reference book for professionals and practitioners with an interest in lipids. The book is also suitable for upper-level undergraduate, graduate, and postgraduate instruction. Scientists and professionals, who have left the university and are engaged in research and development in the industry, government, regulatory, or academics will find this book a useful reference. In this edition, I have deleted some chapters and renamed some chapters and/or had new authors rewrite some of the old chapters with updated references and added many new chapters to reflect current knowledge and interests. In other words, the new edition represents a substantial change from the previous editions. Section I increased from seven to nine chapters and Section II from three to seven, Section III decreased from eight to five, Section IV still has nine chapters but some are new, and Section V increased from five to seven. A great effort was made to recruit and select contributors who are internationally rec- ognized experts. I thank the new authors and the prior authors who updated their chapters for their exceptional attention to detail and timely submission of their manuscripts. Overall, there are 37 chapters in the fourth edition, and the text has been updated with new and available information. Again, some chapters were removed and new ones added. The new additions or modifications are Chapters 2, 6, 8 through 11, 13 through 17, 20, 22 through 24, 26, 28 through 32, 36, and 37. It is almost impossible to cover all aspects of lipids. I feel that with the added chapters, the book covered most topics that are of interest to our readers. The book is divided into five main sections: chemistry and properties, processing and food applications, oxidation and antioxidants, nutrition, and biotechnology and biochemistry. I remain grateful to the readers and users of the previous editions and sincerely hope that the much improved and updated fourth edition will meet your satisfaction. Comments on this edition are welcomed. Based on the comments of readers and reviewers of the past editions, I hope that the current edition is an improvement with new chapters and new ways of studying and utilizing lipids to benefit our profession and consumers. I apologize in advance for any errors and urge you to contact me or the publisher if you find mistakes or have suggestions to improve the readability and comprehension of this text. Special thanks go to our readers and to the editorial staff at Taylor & Francis Group, LLC, for their expertise, suggestions, and completing the publication on time. Casimir C. Akoh ix