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Handbook of

Peter C.K. Cheung Editor-in-Chief

Bhavbhuti M. Mehta Editor

Handbook of

With 209 Figures and 179 Tables Editor-in-Chief Peter C.K. Cheung Food and Nutritional Sciences Program School of Life Sciences The Chinese of Hong Kong Shatin, New Territories Hong Kong, China

Editor Bhavbhuti M. Mehta Chemistry Department Sheth M.C. College of Dairy Science Anand Agricultural University Anand, Gujarat, India

ISBN 978-3-642-36604-8 ISBN 978-3-642-36605-5 (eBook) ISBN 978-3-642-36606-2 (print and electronic bundle) DOI 10.1007/978-3-642-36605-5

Library of Congress Control Number: 2015950199

Springer Heidelberg New York Dordrecht London # Springer-Verlag Berlin Heidelberg 2015 This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. The publisher, the authors and the editors are safe to assume that the advice and information in this book are believed to be true and accurate at the date of publication. Neither the publisher nor the authors or the editors give a warranty, express or implied, with respect to the material contained herein or for any errors or omissions that may have been made.

Printed on acid-free paper

Springer-Verlag GmbH Berlin Heidelberg is part of Springer Science+Business Media (www.springer. com) This book is dedicated to my family members: Carmen, Timothy, Rebekah, and Anthony. Peter C.K. Cheung

Preface

Food chemistry, unlike other branches of chemistry which focus on a particular class of compounds, is a very broad field that encompasses many different aspects. Food chemistry is involved not only in the determination of the chemical compo- sition of the raw materials and food products but also deals with the desirable and undesirable changes which occur in during their production and storage. Since food is a very complex matrix by its nature, the chemical reactions of its constituents are very complicated and affect the nutritional value, toxicological and safety aspects, as well as the sensory quality of the food. Food chemistry is also closely related to the technological and economic aspects in the food manufacturing industry, catering, and health food business. This Handbook is intended to be a comprehensive reference for the various chemical aspects of foods and food commodities. Apart from the traditional knowl- edge, this book will cover the most recent research and development of food chemistry in the areas of functional foods and , organic and geneti- cally modified foods, and . This Handbook is divided into the following seven parts:

Part 1: Introduction encompasses the overview of food chemistry, which includes the general properties of major and minor food components; the major categories of food additives including , dietary ingredients, processing aids, flavors, sweeteners, colors, and texturizers as well as the applications of these food additives in general. This part aims at providing some basic information for those who may not have the background knowledge of food chemistry and can be read as an independent introductory section. Part 2: Principles of Chemical of Food Components provides a very concise coverage of the basic chemical analysis of food components, which highlights some classical methods, sampling and sample prepa- ration, and instrumental food analysis. The purpose of this part is to outline some of the essentials of food analysis which are used to determine the chemical composition of food and food commodities mentioned in Part 3. Part 3: Chemical Composition of Food and Food Commodities is the major section in this Handbook, which consists of 12 categories including natural foods and food commodities from plant and animal origin as well as genetically modified

vii viii Preface

and organic ones. Some common processed food products are also included to reflect the diversity of food commodities. The information in this part should give the readers a comprehensive knowledge of the chemical composition of most of the major food groups listed in a food composition database. Part 4: Chemical and Toxicological Aspects of Food is a special section which aims at covering the various types of from plant and microbial origins as well as the different chemical toxicants that are likely to cause food contamination. Both the chemical nature and toxicological aspects of all these natural and man-made contaminants/toxicants are essential for evalu- ating the safety of our foods and food products. Part 5: Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and During Processing focuses on the possible chemical changes of food components in regard to their nutritional and toxicological aspects during conventional thermal processing methods including heating, freezing, and drying as well as the unconventional pressure-assisted thermal processing. Emphasis in this part is on the chemical degradation of food com- ponents leading to the formation of harmful substances during processing and their implications to and health risk. Part 6: Chemistry of Bioactive Ingredients in Functional Foods and Nutraceuticals highlights the chemical properties of natural bioactive substances that are from plant, animal, and microbial origin as well as synthetic ones. This information will be useful for those who want to apply these substances as bioactive ingredients in functional foods and nutraceuticals for human consumption. Part 7: Chemistry of Food Nanotechnology covers a few areas related to food nanotechnology including an introduction to food nanotechnology and its appli- cation in food safety via the development of as well as nanomaterials used for . It reflects the very rapid and promising development in food nanotechnology that would attract great attention in the near future.

This book should be appropriate for undergraduates and postgraduates in the academics and professionals from the various disciplines and industries who are interested in applying knowledge of food chemistry in their respective fields.

Peter C.K. Cheung Acknowledgments

We would like to express our most sincere thanks and appreciation to all the section editors for their strong commitment and hard work for this Handbook as well as all the chapter authors for their significant contribution. We also sincerely acknowl- edge the very professional and efficient support by Ms Nivedita Baroi from the Reference Editorial Office, Springer. The excellent editorial support from Ms Audrey Wong and her team from Springer (Singapore) has also greatly facilitated the preparation of this Handbook.

ix

Contents

Part I Introduction ...... 1

1 Overview of Food Chemistry ...... 3 Bhavbhuti M. Mehta and Peter C.K. Cheung 2 General Properties of Major Food Components ...... 15 Christofora Hanny Wijaya, Wahyu Wijaya, and Bhavbhuti M. Mehta 3 General Properties of Minor Food Components ...... 55 Christofora Hanny Wijaya, Wahyu Wijaya, and Bhavbhuti M. Mehta 4 Chemical Properties and Applications of Food Additives: Preservatives, Dietary Ingredients, and Processing Aids ...... 75 Pak Nam Albert Chan 5 Chemical Properties and Applications of Food Additives: , Sweeteners, Food Colors, and Texturizers ...... 101 Pak Nam Albert Chan

Part II Principles of Chemical Analysis of Food Components .... 131

6 Classical Wet Chemistry Methods ...... 133 Semih Otles and Vasfiye Hazal Ozyurt 7 Sampling and Sample Preparation ...... 151 Semih Otles and Vasfiye Hazal Ozyurt 8 Instrumental Food Analysis ...... 165 Semih Otles and Vasfiye Hazal Ozyurt

Part III Chemical Composition of Food and Food Commodities ...... 189

9 Chemical Composition of Bakery Products ...... 191 Cristina M. Rosell and Raquel Garzon

xi xii Contents

10 Chemical Composition of Beverages and Drinks ...... 225 Alan J. Buglass 11 Chemical Composition of Cereals and Their Products ...... 301 Zeynep Tacer-Caba, Dilara Nilufer-Erdil, and Yongfeng Ai 12 Chemical Composition of Eggs and Egg Products ...... 331 Hoon H. Sunwoo and Naiyana Gujral 13 Chemical Composition of and Oil Products ...... 365 Jill K. Winkler-Moser and Bhavbhuti M. Mehta 14 Chemical Composition of Fish and Fishery Products ...... 403 Zulema Coppes Petricorena 15 Chemical Composition of Food Products from Genetically Modified Organisms ...... 437 Wilna Jansen-van-Rijssen and E. Jane Morris 16 Chemical Composition of and Meat Products ...... 471 Ángel Cobos and Olga Dı´az 17 Chemical Composition of and Milk Products ...... 511 Bhavbhuti M. Mehta 18 Chemical Composition of Organic Food Products ...... 555 Flavio Paoletti 19 Chemical Composition of and Confectionery Products . . . 585 Andrea Hinkova, Zdenek Bubnik, and Pavel Kadlec 20 Chemical Composition of Vegetables and Their Products ...... 627 Monica Butnariu and Alina Butu

Part IV Chemical and Toxicological Aspects of Food Contamination ...... 693

21 Agricultural Chemical Pollutants ...... 695 April R. Van Scoy, James N. Seiber, and Ronald S. Tjeerdema 22 Contamination from Industrial Toxicants ...... 719 Corey M. Griffith, Nausheena Baig, and James N. Seiber 23 Plant-Associated Natural Food Toxins ...... 753 Steven M. Colegate, Dale R. Gardner, and Stephen T. Lee 24 Natural Food Toxins of Bacterial Origin ...... 785 Luisa W. Cheng, Kirkwood M. Land, and Larry H. Stanker Contents xiii

25 Model Fungal Systems for Investigating Food Plant ...... 809 Jong H. Kim and Kathleen L. Chan

Part V Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and Nutrients During Processing ...... 831

26 Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and Nutrients During Drying ...... 833 Nathamol Chindapan, Chalida Niamnuy, and Sakamon Devahastin

27 Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and Nutrients During Freezing ...... 867 To˜nu Pussa€

28 Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and Nutrients During Heating and Cooking ...... 897 Bhavbhuti M. Mehta

29 Pressure Effects on the Rate of Chemical Reactions Under the High Pressure and High Temperature Conditions Used in Pressure-Assisted Thermal Processing ...... 937 Vinicio Serment-Moreno, Kai Deng, Xulei Wu, Jorge Welti-Chanes, Gonzalo Velazquez, and J. Antonio Torres

Part VI Chemistry of Bioactive Ingredients in Functional Foods and Nutraceuticals ...... 965

30 Bioactive Substances of Plant Origin ...... 967 Yueliang Zhao, YiZhen Wu, and Mingfu Wang

31 Bioactive Substances of Animal Origin ...... 1009 Xinchen Zhang, Feng Chen, and Mingfu Wang

32 Bioactive Substances of Microbial Origin ...... 1035 Wenping , Xuntao Zhu, and Zhaoyong Ba

33 Synthetic Bioactive Substances ...... 1061 Shiming Li xiv Contents

Part VII Chemistry of Food Nanotechnology ...... 1085

34 An Introduction to Food Nanotechnology ...... 1087 Chi-Fai Chau 35 Applications of Nanotechnology in Developing Biosensors for Food Safety ...... 1103 Hsiao-Wei Wen 36 Advances of Nanomaterials for Food Processing ...... 1137 Hsin-Yi Yin and Wen-Che Tsai Index ...... 1161 About the Editors

Peter C.K. Cheung Food and Nutritional Sciences Program, School of Life Sciences, The Chinese Uni- versity of Hong Kong, Shatin, New Territories, Hong Kong, China Professor Peter C.K. Cheung obtained his B.Sc. (Hons.) degree from the University of Hong Kong, majoring in chemistry. He completed a master’s degree in food and drug chemistry and a Ph.D. degree in food from the University of New South Wales in Australia. He is currently the Program Director of Food and Nutritional Sciences in the School of Life Sciences at the Chinese University of Hong Kong. Professor Cheung’s expertise is on the chemistry and biology of bioactive food components. His research is focused on the structure and function of dietary fiber. He has particular interest in the chemical structure and biological functions of mushroom and fungal , especially their antioxidant, antitumor, immunomodu- latory, and prebiotic activities. Professor Cheung is serving as the associate editor of Bioactive Carbohydrates and Dietary Fiber and the editorial board member of the International Journal of Medicinal Mushrooms, Journal of Agricultural and Food Chemistry, Journal of Food Composition and Analysis, as well as and Human Wellness.He is the author or coauthor of over 100 SCI publications and is the editor of the book Mushrooms as Functional Foods.

xv xvi About the Editors

Bhavbhuti M. Mehta Dairy Chemistry Department, Sheth M.C. College of Dairy Science, Anand Agricul- tural University, Anand, Gujarat, India Dr. Bhavbhuti M. Mehta is an Assistant Professor in the Dairy Chemistry Department, Sheth M.C. College of Dairy Science at Anand Agricultural University, Anand, Gujarat, India. He did his B.Tech. (Dairy Tech- nology) and M.Sc. (Dairying) in the field of dairy chemistry as a major subject and dairy as a minor subject as well as Ph.D. in the field of dairy chemistry as a major subject and dairy technology as a minor subject from Sheth M.C. College of Dairy Science, Anand Agricultural University, Anand, Gujarat, India. He teaches various subjects on dairy and food chemistry at undergraduate as well as postgraduate levels. His major specialty is various physicochemical changes (process-induced changes) taking place during processing of milk and milk products and food chemistry in general. His research interests also include oxidation and its prevention (natural antioxidants), methods to measure various oxidative deteriorations, functional food ingredients, and neutraceuticals (e.g., milk fat globule membrane), natural alternatives to food additives (e.g., ice-structuring in ice cream and frozen desserts), role of various constituents in dairy and food products (viz. flavors, off-flavors, texture, structure, etc.), and chemistry and technology of milk and dairy products (e.g., , yoghurt, fat-rich dairy products, concentrated , dried milk, ice cream) in particular and food products in general. He is an associate editor of the Interna- tional Journal of Dairy Technology and an editorial board member and a referee/ reviewer in a number of journals. He has published a number of technical/research/ review papers/chapters/booklets/abstracts/monographs in national as well as inter- national journals, seminars, and conferences. He has edited one book published by the CRC Press, Taylor & Francis Group. Section Editors

Part 1: Introduction Peter C.K. Cheung Food and Nutritional Sciences Program, School of Life Sciences, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China Bhavbhuti M. Mehta Dairy Chemistry Department, SMC College of Dairy Science Anand Agricultural University, Anand, Gujarat, India Part 2: Principles of Chemical Analysis of Food Components Semih Otles Food Department, Faculty of Engineering Ege University, Bornova, Izmir, Turkey Part 3: Chemical Composition of Food and Food Commodities Peter C.K. Cheung Food and Nutritional Sciences Program, School of Life Sciences, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China Bhavbhuti M. Mehta Dairy Chemistry Department, SMC College of Dairy Science Anand Agricultural University, Anand, Gujarat, India Part 4: Chemical and Toxicological Aspects of Food Contamination John J. Beck Foodborne Detection and Prevention, USDA-ARS, WRRC, Albany, CA, USA Part 5: Nutritional and Toxicological Aspects of the Chemical Changes of Food Components and Nutrients During Processing Bhavbhuti M. Mehta Dairy Chemistry Department, SMC College of Dairy Science, Anand Agricultural University, Anand, Gujarat, India

xvii xviii Section Editors

Part 6: Chemistry of Bioactive Ingredients in Functional Foods and Nutraceuticals Mingfu Wang School of Biological Sciences, The University of Hong Kong, Hong Kong, China S.A.R. Part 7: Chemistry of Food Nanotechnology Chi Fai Chau Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan, R.O.C. Contributors

Yongfeng Ai Department of Food Science and Human , Michigan State University, East Lansing, MI, USA Zhaoyong Ba Department of Food Science, Pennsylvania State University, University Park, PA, USA Nausheena Baig Foodborne Toxin Detection and Prevention, Agricultural Research Service, Western Regional Research Center, U.S. Department of Agriculture, Albany, CA, USA Zdenek Bubnik Department of Carbohydrates and Cereals, Institute of Chemical Technology, Prague, Czech Republic Alan J. Buglass Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon, Republic of Korea Monica Butnariu Banat’s University of Agricultural Sciences and Veterinary Medicine, “Regele Mihai I al Romaˆniei”, Timisoara, Romania Alina Butu National Institute of Research and Development for Biological Sciences, Bucharest, Romania Kathleen L. Chan U.S. Department of Agriculture, Foodborne Toxin Detection and Prevention Research Unit, Agricultural Research Service, Albany, CA, USA Pak Nam Albert Chan School of Life Sciences, The Chinese University of Hong Kong, Tsuen Wan New Town, Hong Kong Chi-Fai Chau Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan, Republic of China Feng Chen Institute for Food and Bioresource Engineering, College of - ing, Peking University, Beijing, China Luisa W. Cheng Agricultural Research Service, U.S. Department of Agriculture, Foodborne Toxin Detection and Prevention Research Unit, Western Regional Research Center, Albany, CA, USA

xix xx Contributors

Peter C.K. Cheung Food and Nutritional Sciences Program, School of Life Sciences, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China Nathamol Chindapan Department of , Faculty of Science, Siam University, Bangkok, Thailand A´ ngel Cobos Department of , Nutrition and Food Science, Food Technology Division, Faculty of Sciences, University of Santiago de Compostela, Lugo, Spain Steven M. Colegate Agricultural Research Service, U.S. Department of Agriculture, Poisonous Plant Research Laboratory, Logan, UT, USA Zulema Coppes Petricorena Department of (DEPBIO), Faculty of Chemistry, UDELAR, Montevideo, Uruguay Olga Dı´az Department of Analytical Chemistry, Nutrition and Food Science, Food Technology Division, Faculty of Sciences, University of Santiago de Compostela, Lugo, Spain Kai Deng Food Group, Department of Food Science & Technology, Oregon State University, Corvallis, OR, USA Sakamon Devahastin Department of , Faculty of Engineering, King Mongkut’s University of Technology Thonburi, Bangkok, Thailand Dale R. Gardner Agricultural Research Service, U.S. Department of Agriculture, Poisonous Plant Research Laboratory, Logan, UT, USA Raquel Garzon Department of Food Science, Institute of Agrochemistry and Food Technology, Spanish Research Council, IATA-CSIC, Paterna, Valencia, Spain Corey M. Griffith Foodborne Toxin Detection and Prevention, Agricultural Research Service, Western Regional Research Center, U.S. Department of Agriculture, Albany, CA, USA Department of Chemistry, Environmental Toxicology Graduate Program, Univer- sity of California, Riverside, CA, USA Naiyana Gujral 3-142H KATZ Group for Health Research, Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, AB, Canada Andrea Hinkova Department of Carbohydrates and Cereals, Institute of Chemical Technology, Prague, Czech Republic Wilna Jansen-van-Rijssen Department of Paraclinical Sciences, Faculty of Veterinary Science, University of Pretoria, Onderstepoort, South Africa Pavel Kadlec Department of Carbohydrates and Cereals, Institute of Chemical Technology, Prague, Czech Republic Contributors xxi

Jong H. Kim U.S. Department of Agriculture, Foodborne Toxin Detection and Prevention Research Unit, Agricultural Research Service, Albany, CA, USA Kirkwood M. Land Department of Biological Sciences, University of the Pacific, Stockton, CA, USA Stephen T. Lee Agricultural Research Service, U.S. Department of Agriculture, Poisonous Plant Research Laboratory, Logan, UT, USA Shiming Li College of Life Sciences, Huanggang Normal University, Huanggang, Hubei, China Bhavbhuti M. Mehta Dairy Chemistry Department, SMC College of Dairy Science, Anand Agricultural University, Anand, Gujarat, India E. Jane Morris School of Biology, University of Leeds, Leeds, UK Chalida Niamnuy Deparment of , Faculty of Engineering, Kasetsart University, Bangkok, Thailand Dilara Nilufer-Erdil Department of Food Engineering, Faculty of Chemical and Metallurgical Engineering, Istanbul Technical University, Maslak, Istanbul, Turkey Semih Otles Faculty of Engineering, Food Engineering Department, Ege University, Bornova, Izmir, Turkey Vasfiye Hazal Ozyurt Faculty of Engineering, Food Engineering Department, Ege University, Bornova, Izmir, Turkey To˜nu Pu¨ssa Institute of Veterinary Medicine and Animal Sciences, Department of Food , Estonian University of Life Sciences, Tartu, Estonia Flavio Paoletti Centre of Research on Food and Nutrition (CRA-), Agricultural Research Council (CRA), Rome, Italy Cristina M. Rosell Department of Food Science, Institute of Agrochemistry and Food Technology, Spanish Research Council, IATA-CSIC, Paterna, Valencia, Spain James N. Seiber Department of Environmental Toxicology, College of Agricul- tural and Environmental Sciences, University of California, Davis, CA, USA Vinicio Serment-Moreno Centro de Biotecnologı´a FEMSA, Escuela de Ingenierı´a y Ciencias, Tecnolo´gico de Monterrey, Monterrey, NL, Mexico Larry H. Stanker Agricultural Research Service, U.S. Department of Agricul- ture, Foodborne Toxin Detection and Prevention Research Unit, Western Regional Research Center, Albany, CA, USA Hoon H. Sunwoo 3-142H KATZ Group for Health Research, Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, AB, Canada xxii Contributors

Zeynep Tacer-Caba Department of Food Engineering, Faculty of Chemical and Metallurgical Engineering, Istanbul Technical University, Maslak, Istanbul, Turkey Wenping Tang Department of Food Science, Rutgers University, New Bruns- wick, NJ, USA Ronald S. Tjeerdema Department of Environmental Toxicology, College of Agricultural and Environmental Sciences, University of California, Davis, CA, USA J. Antonio Torres Food Process Engineering Group, Department of Food Science & Technology, Oregon State University, Corvallis, OR, USA Wen-Che Tsai Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan April R. Van Scoy Department of Environmental Toxicology, College of Agricultural and Environmental Sciences, University of California, Davis, CA, USA Gonzalo Velazquez Instituto Polite´cnico Nacional, CICATA-Qro., Quere´taro, Qro., Mexico Mingfu Wang School of Biological Sciences, The University of Hong Kong, Hong Kong, China Jorge Welti-Chanes Centro de Biotecnologı´a FEMSA, Escuela de Ingenierı´ay Ciencias, Tecnolo´gico de Monterrey, Monterrey, NL, Mexico Hsiao-Wei Wen Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan Christofora Hanny Wijaya Food Chemistry Research Division, Department of Food Science and Technology, Bogor Agricultural University, Bogor, Indonesia Wahyu Wijaya Particle and Interfacial Technology Group, Department of Applied Analytical and , Faculty of Bioscience Engineering, Ghent University, Ghent, Belgium Jill K. Winkler-Moser Functional Foods Research Unit, United States Department of Agriculture (USDA), Agricultural Research Service (ARS), National Center for Agricultural Utilization Research (NCAUR), Peoria, IL, USA YiZhen Wu School of Biological Sciences, The University of Hong Kong, Hong Kong, China Xulei Wu Food Process Engineering Group, Department of Food Science & Technology, Oregon State University, Corvallis, OR, USA Hsin-Yi Yin Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan Contributors xxiii

Xinchen Zhang School of Biological Sciences, The University of Hong Kong, Hong Kong, China Yueliang Zhao School of Biological Sciences, The University of Hong Kong, Hong Kong, China Xuntao Zhu Department of Food Science, Nutrition and Management, Delaware Valley University, Doylestown, PA, USA