FOOD LIPIDS Chemistry, Nutrition, and Biotechnology ppt

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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

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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

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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 Polymorphism of Fats........................................................................ 245

Patrick J. Lawler and Paul S. Dimick

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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. Eitenmiller

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

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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 Obesity................................................................................................... 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

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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 research 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 have 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

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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 coauthor 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 his 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.

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Contributors

Casimir C. Akoh

Department of Food Science and Technology

University of Georgia

Athens, Georgia

Angela D. Bell

Department of Chemistry

Auburn University

Auburn, Alabama

Eunok Choe

Department of Food and Nutrition

Inha University

Incheon, Korea

Eric A. Decker

Department of Food Science

University of Massachusetts

Amherst, Massachusetts

Anthony J. Del Vecchio

Monsanto, Inc.

Davis, California

Paul S. Dimick

Department of Food Science

Pennsylvania State University

University Park, Pennsylvania

Ronald R. Eitenmiller

Department of Food Science and Technology

University of Georgia

Athens, Georgia

Marilyn C. Erickson

Center for Food Safety

Department of Food Science and Technology

University of Georgia

Griffin, Georgia

J. Bruce German

Department of Food Science and Technology

University of California

Davis, California

Howard Perry Glauert

Department of Nutrition and Food Science

University of Kentucky

Lexington, Kentucky

Barbara Mullen Grossman

Department of Foods and Nutrition

University of Georgia

Athens, Georgia

Frank D. Gunstone

Scottish Crop Research Institute

Invergowrie, Dundee, Scotland

Dorothy B. Hausman

Department of Foods and Nutrition

University of Georgia

Athens, Georgia

Lawrence A. Johnson

Center for Crops Utilization Research

Department of Food Science and Human

Nutrition

Iowa State University

Ames, Iowa

Byung Hee Kim

Department of Food Science and Technology

University of Georgia

Athens, Georgia

Hyun Jung Kim

Department of Food Science and Technology

Ohio State University

Columbus, Ohio

David M. Klurfeld

United States Department of Agriculture

Agricultural Research Service

Beltsville, Maryland

Vic C. Knauf

Monsanto, Inc.

Davis, California

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David Kritchevsky (Late)

Wistar Institute

Philadelphia, Pennsylvania

Oi-Ming Lai

Department of Bioprocess Technology

Universiti Putra Malaysia

Serdang Selangor, Malaysia

Patrick J. Lawler

McCormick and Company, Inc.

Cockeysville, Maryland

Shengrong Li

Department of Chemistry

Auburn University

Auburn, Alabama

Yong Li

Department of Food Science

Purdue University

West Lafayette, Indiana

Dorris A. Lillard

Department of Food Science and Technology

University of Georgia

Athens, Georgia

Alejandro G. Marangoni

Department of Food Science

University of Guelph

Guelph, Ontario, Canada

D. Julian McClements

Department of Food Science

University of Massachusetts

Amherst, Massachusetts

Richard E. McDonald

Food and Drug Administration

National Center for Food Safety and

Technology

Summit-Argo, Illinois

Ronald P. Mensink

Department of Human Biology

Maastricht University

Maastricht, The Netherlands

David B. Min

Department of Food Science and Technology

Ohio State University

Columbus, Ohio

Kazuo Miyashita

Graduate School of Fisheries Sciences

Hokkaido University

Hakodate, Japan

Magdi M. Mossoba

Food and Drug Administration

Center for Food Safety and Applied Nutrition

College Park, Maryland

Kumar D. Mukherjee

Institute for Lipid Research

Federal Research Centre for Nutrition and Food

Munster, Germany

Sean Francis O’Keefe

Department of Food Science and Technology

Virginia Polytechnic Institute and State

University

Blacksburg, Virginia

Edward J. Parish

Department of Chemistry

Auburn University

Auburn, Alabama

Jogchum Plat

Department of Human Biology

Maastricht University

Maastricht, The Netherlands

David W. Reische

Dannon Company, Inc.

Fort Worth, Texas

Dérick Rousseau

School of Nutrition

Ryerson Polytechnic University

Toronto, Ontario, Canada

Fereidoon Shahidi

Department of Biochemistry

Memorial University of Newfoundland

St. John’s, Newfoundland, Canada

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P.K.J.P.D. Wanasundara

Agriculture Agri-Food Canada

Saskatoon Research Centre

Saskatoon, Saskatchewan, Canada

Udaya N. Wanasundara

POS Pilot Plant Corporation

Saskatoon, Canada

Kathleen Warner

National Center for Agricultural Utilization

Research

Agricultural Research Service

U.S. Department of Agriculture

Peoria, Illinois

Bruce A. Watkins

Department of Food Science

Purdue University

West Lafayette, Indiana

Steven M. Watkins

FAME Analytics

West Sacramento, California

Nikolaus Weber

Institute for Lipid Research

Federal Research Centre for Nutrition and Food

Munster, Germany

John D. Weete

West Virginia University

Morgantown, West Virginia

Wendy M. Willis

Yves Veggie Cuisine

Vancouver, British Columbia, Canada

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Part I

Chemistry and Properties

Akoh/Food Lipids: Chemistry, Nutrition, and Biotechnology 46632_C001 Final Proof page 1 21.1.2008 10:20pm Compositor Name: PJayaraj