Food chemistry by fennema 3rd ed

Pag e i Food Chemistry Third Edition Edited by Owen R Fennema University of WisconsinMadison Madison, Wisconsin M ARCEL DEKKER, INC NEW YORK • BASEL • HONG KONG Pag e ii Library of Congress Cataloging-in-Publication Data Food chemistry / edited by Owen R Fennema — 3rd ed p cm — (Food science and technology) Includes index ISBN 0-8247-9346-3 (cloth : alk paper) — ISBN 0-8247-9691-8 (paper : alk paper) Food—Analysis Food—Composition I Fennema, Owen R II Series: Food science and technology (Marcel Dekker, Inc.); v 76 TX541.F65 1996 664'.001'54—dc20 96-19500 CIP The publisher offers discounts on this book when ordered in bulk quantities For more information, write to Special Sales/Professional Marketing at the address below This book is printed on acid-free paper Copyright © 1996 by Marcel Dekker, Inc All Rights Reserved Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage and retrieval system, without permission in writing from the publisher Marcel Dekker, Inc 270 Madison Avenue, New York, New York 10016 Current printing (last digit): 10 PRINTED IN THE UNITED STATES OF AMERICA Pag e iii Preface to the Third Edition More than a decade has passed since the publication of the second edition of Food Chemistry, so the appropriateness of an updated version should be apparent The purposes of the book remain unchanged: it is primarily a textbook for upper division undergraduates and beginning graduate students who have sound backgrounds in organic chemistry and biochemistry, and is secondarily a reference book Information on food analysis is intentionally absent, except where its presence fits logically with the topic under discussion As a textbook for undergraduates, it is designed to serve as the basis of a two-semester course on food chemistry with the assumption that the instructor will make selective reading assignments as deemed appropriate Individual chapters in the book should be useful as the basis of graduate-level courses on specialized topics in food chemistry The third edition differs in several important respects from the second The chapters prepared by first-time contributors are totally new These cover such topics as proteins, dispersions, enzymes, vitamins, minerals, animal tissues, toxicants, and pigments Chapters by contributors to the second edition have been thoroughly revised For example, in the chapter “Water and Ice,” a major addition deals with molecular mobility and glass transition phenomena The result is a book that is more than 60% new, has greatly improved graphics, and is better focused on material that is unique to food chemistry Chapters have been added on the topics of dispersions and minerals In the second edition, treatment of dispersions was accomplished in the chapters “Lipids,” “Proteins,” and “Carbohydrates,” and minerals were covered in the chapter “Vitamins and Minerals.” Although this was organizationally sound, the result was superficial treatment of dispersions and minerals The new chapters on these topics provide depth of coverage that is more consistent with the remainder of the book Associated with these changes is a chapter, written by a new contributor, that is now devoted solely to vitamins It is my belief that this chapter represents the first complete, in-depth treatise on vitamins with an emphasis on food chemistry I would be remiss not to thank the contributors for their hard work and tolerance of my sometimes severe editorial oversight They have produced a book that is of first-rate quality After twenty years and two previous editions, I am finally satisfied that all major topics are covered appropriately with regard to breadth and depth of coverage, and that a proper focus on reactions pertaining specifically to foods has been achieved This focus successfully dis- Pag e iv tinguishes food chemistry from biochemistry in the same sense that biochemistry is distinct from, yet still dependent on, organic chemistry Although I have planned and edited this edition with great care, minor errors are inevitable, especially in the first printing If these are discovered, I would very much appreciate hearing from you so that corrections can be effected promptly OWEN R FENNEMA Pag e ix Contents Preface to the Third Edition iii Preface to the Second Edition v Preface to the First Edition vii Contributors xi Introduction to Food Chemistry Owen R Fennema and Steven R Tannenbaum Water and Ice Owen R Fennema 17 Dispersed Systems: Basic Considerations Pieter Walstra 95 Carbohydrates James N BeMiller and Roy L Whistler 157 Lipids Wassef W Nawar 225 Amino Acids, Peptides, and Proteins Srinivasan Damodaran 321 Enzymes John R Whitaker 431 Vitamins Jesse F Gregory III 531 Minerals Dennis D Miller 617 Pag e v Preface to the Second Edition Considerable time has passed since publication of the favorably received first edition so a new edition seems appropriate The purpose of the book remains unchanged—it is intended to serve as a textbook for upper division undergraduates or beginning graduate students who have sound backgrounds in organic chemistry and biochemistry, and to provide insight to researchers interested in food chemistry Although the book is most suitable for a two-semester course on food chemistry, it can be adapted to a one-semester course by specifying selective reading assignments It should also be noted that several chapters are of sufficient length and depth to be useful as primary source materials for graduate-level specialty courses This edition has the same organization as the first, but differs substantially in other ways The chapters on carbohydrates, lipids, proteins, flavors, and milk and the concluding chapter have new authors and are, therefore, entirely new The chapter on food dispersions has been deleted and the material distributed at appropriate locations in other chapters The remaining chapters, without exception, have been substantially modified, and the index has been greatly expanded, including the addition of a chemical index Furthermore, this edition, in contrast to the first, is more heavily weighted in the direction of subject matter that is unique to food chemistry, i.e., there is less overlap with materials covered in standard biochemistry courses Thus the book has undergone major remodeling and refinement, and I am indebted to the various authors for their fine contributions and for their tolerance of my sometimes severe editorial guidance This book, in my opinion, provides comprehensive coverage of the subject of food chemistry with the same depth and thoroughness that is characteristic of the better quality introductory textbooks on organic chemistry and biochemistry This, I believe, is a significant achievement that reflects a desirable maturation of the field of food chemistry OWEN R FENNEMA Pag e vii Preface to the First Edition For many years, an acute need has existed for a food chemistry textbook that is suitable for food science students with backgrounds in organic chemistry and biochemistry This book is designed primarily to fill the aforementioned need, and secondarily, to serve as a reference source for persons involved in food research, food product development, quality assurance, food processing, and in other activities related to the food industry Careful thought was given to the number of contributors selected for this work, and a decision was made to use different authors for almost every chapter Although involvement of many authors results in potential hazards with respect to uneven coverage, differing philosophies, unwarranted duplication, and inadvertent omission of important materials, this approach was deemed necessary to enable the many facets of food chemistry to be covered at a depth adequate for the primary audience Since I am acutely aware of the above pitfalls, care has been taken to minimize them, and I believe the end product, considering it is a first edition, is really quite satisfying—except perhaps for the somewhat generous length If the readers concur with my judgment, I will be pleased but unsurprised, since a book prepared by such outstanding personnel can hardly fail, unless of course the editor mismanages the talent Organization of the book is quite simple and I hope appropriate Covered in sequence are major constituents of food, minor constituents of food, food dispersions, edible animal tissues, edible fluids of animal origin, edible plant tissues and interactions among food constituents—the intent being to progress from simple to more complex systems Complete coverage of all aspects of food chemistry, of course, has not been attempted It is hoped, however, that the topics of greatest importance have been treated adequately In order to help achieve this objective, emphasis has been given to broadly based principles that apply to many foods Figures and tables have been used liberally in the belief that this approach facilitates understanding of the subject matter presented The number of references cited should be adequate to permit easy access to additional information To all readers I extend an invitation to report errors that no doubt have escaped my attention, and to offer suggestions for improvements that can be incorporated in future (hopefuly) editions Since enjoyment is an unlikely reader response to this book, the best I can hope for is that readers will find it enlightening and well suited for its intended purpose OWEN R FENNEMA Pag e x 10 Colorants J H von Elbe and Steven J Schwartz 651 11 Flavors Robert C Lindsay 723 12 Food Additives Robert C Lindsay 767 13 Toxic Substances Michael W Pariza 825 14 Characteristics of Milk Harold E Swaisgood 841 15 Characteristics of Edible Muscle Tissues E Allen Foegeding, Tyre C Lanier, and Herbert O Hultin 879 16 Characteristics of Edible Plant Tissues Norman F Haard and Grady W Chism 943 17 Summary: Integrative Concepts Petros Taoukis and Theodore P Labuza 1013 Appendices A International System of Units (SI), The Modernized Metric System 1043 B Conversion Factors (Non-SI Units to SI Units) 1047 C Greek Alphabet 1048 Index 1051 Pag e xi Contributors James N BeMiller Department of Food Science, Purdue University, West Lafayette, Indiana Grady W Chism Department of Food Science and Technology, The Ohio State University, Columbus, Ohio Srinivasan Damodaran Department of Food Science, University of Wisconsin—Madison, Madison, Wisconsin Owen R Fennema Department of Food Science, University of Wisconsin—Madison, Madison, Wisconsin E Allen Foegeding Department of Food Science, North Carolina State University, Raleigh, North Carolina Jesse F Gregory III Department of Food Science and Human Nutrition, University of Florida, Gainesville, Florida Norman F Haard Department of Food Science and Technology, Institute of Marine Resources, University of California, Davis, California Herbert O Hultin Department of Food Science, University of Massachusetts, Amherst, Massachusetts Theodore P Labuza Department of Food Science and Nutrition, University of Minnesota, St Paul, Minnesota Tyre C Lanier Department of Food Science, North Carolina State University, Raleigh, North Carolina Robert C Lindsay Department of Food Science, University of Wisconsin—Madison, Madison, Wisconsin Dennis D Miller Department of Food Science, Cornell University, Ithaca, New York Pag e xii Wassef W Nawar Department of Food Science, University of Massachusetts, Amherst, Massachusetts Michael W Pariza Department of Food Microbiology and Toxicology, Food Research Institute, University of Wisconsin—Madison, Madison, Wisconsin Steven J Schwartz* Department of Food Science, North Carolina State University, Raleigh, North Carolina Harold E Swaisgood Department of Food Science, North Carolina State University, Raleigh, North Carolina Steven R Tannenbaum Department of Chemistry, Division of Toxicology, Massachusetts Institute of Technology, Cambridge, Massachusetts Petros Taoukis Department of Chemical Engineering, National Technical University of Athens, Athens, Greece J H von Elbe Department of Food Science, University of Wisconsin—Madison, Madison, Wisconsin Pieter Walstra Department of Food Science, Wageningen Agricultural University, Wageningen, The Netherlands Roy L Whistler Department of Biochemistry, Purdue University, West Lafayette, Indiana John R Whitaker Department of Food Science and Technology, University of California, Davis, California * Present affiliation: The Ohio State University, Columbus, Ohio definition of, 87 muscle contraction and, 897 Release and antistick agents, 814-815 Restriction enzymes, 519, 520 Retinoids, 545, 546, 547 Retrogradation of starch, 196, 198 Reversible (lyophilic) colloid, 98 Reversion flavors, 308-309 Rheology at the interface, 110 Riboflavin: as a colorant, 717 Pag e 1064 [Riboflavin] stability of, 533 See also Vitamin B2 Rice, lipid content of, 958 Root crops, 967 Rosanoff structure of D-aldose, 161 Rubbery state, definition of, 87 S Saccharin, 794 Safety of food, chemical and biochemical reactions affecting, 7-10 Saffron, 717 Salts, 776-778 in animal-based foods, 778 in meat gels, 936-937 in milk, 853-854 in processed dairy foods, 777-778 Salty taste, 733-734 Sanitizing agents, 815 Sarcomeric proteins, 892, 895-896 Saturated fatty acids, 227 Schaal oven test, 279 Schardinger dextrins, 200 Scheele, Carl Wilhelm, 2-3 Scientific knowledge, interpretation of, 13-14 Seafood, flavor sensations from, 754-755 Sedimentation, 119-121 Selenium: functions in food, 643 RDAs for, 627 Sequestrants See Chelates b-Sheet structure of proteins, 340-342 Shelf life, estimation of, 80-81 Shelf-life case studies, 1028-1037 dehydrated products, 1030-1033 dry dessert mix, 1030-1031 mashed potatoes, 1031-1033 frozen pizza, 1033-1037 Shelf-life modeling, 1016-1029 food-quality function, 1018-1019 principles, 1016-1018 [Shelf-life modeling] simple shelf-life plot approach, 1023-1027 temperature effects, 1019-1023 tests in shelf-life estimates (ASLT principles), 1028-1029 Shiitake mushrooms, flavor sensations from, 740-741 Shikimic acid pathway, flavor sensations from, 743-745 Sitosterol, 959 Small-molecule surfactants, 103 Smoluchowski equation, 61, 121 Smooth (involuntary) muscle, structure of, 890 Societal role of food chemists, 13-14 Sodium, functions in food of, 643 Solvation repulsion, colloids and, 118 Solvent-partitioned enzyme systems, 509-512 advantages, 511 applications, 511-512 in organic solvents, 509-511 Sorbic acid and sorbates, 785-787 Sour taste, 733-734 Spices, flavor sensations from, 747-749 Squid, muscle structure of, 886 Stability of foods: during handling, processing, and storage, 10 estimation of shelf life and, 80-81 hurdle approach to, 83-84 molecular mobility and, 55-83 relative vapor pressure and, 52-55 WLF kinetics and, 81 Stabilizers and thickeners, 800-801, 810 See also Gums Staling of baked goods, 198 Starch, 191-204 amylopectin, 191-192 [Starch] amylose, 191, 192 cold-water swelling, 204 complexes, 198 dietary importance of, 191 granule gelatinization and pasting, 195-196 hydrolysis, 199-201 modified food starch, 201-204 pregelatinized, 204 retrogradation and stalling, 198 uses of, 191, 196-197 Starch gels, 132-133 Starch granules, 192-195 properties of, 102, 193 Starch-sugar transformations in plant tissues, 984-987 State diagram, definition of, 87 Stem crops, 967-968 Stereochemistry of amino acids, 326-327 Stohmann, F., Stokes equation, 120 Stokes-Einstein equation, 61 Storage of food: alterations that can occur during, 7, 8, factors governing stability during, 10 situations encountered during, 10-12 See also Plant tissues, handling and storage Strecker degradation, effect on proteins, 412 Striated (involuntary) muscle, structure of, 890 Structural proteins, 322 Sucrose, 176-178, 796 Sucrose polyester, 804, 805 Sugar: in milk, 853-854 Starch-sugar transformations in plant tissues, 984-987 See also Monosaccharides L-Sugars, 161 Sulfites, 782-784 Sulfur, functions in food, 643 Sulfur dioxide, 782-784 Surface dilational modulus, 110 Pag e 1065 Surfactants, 103-107 functions of, 112 mode of adsorption, 105 surface-tension gradients, 111-112 See also Emulsifiers Sweeteners: low-calorie, 793-798, 818-819 acesulfame K, 795-796 alitame, 796, 797 aspartame, 794-795 cyclamate, 793-794 glycyrrhizin, 797 miraculin, 798 monellin, 798 neohesperidin dihyrochalcone, 797-798 rebaudioside, 797 saccharin, 794 stevioside, 797 sucralose, 796 thaumatins, 798 reduced-calorie, 798-800 Sweetness theories, 725-728 Swelling of gels, 128 Syneresis of gels, 128, 185 T Tannins, 695-696, 736, 962-965 Terpenoids, flavor sensations from, 745-746 Tertiary butylhydroquinone (TBHQ), 286 Texturizers, 820-821 firming types, 806 Thenard, Louis-Jacques, 2, Thermal conductivity of water, 19-20 Thermally induced flavor sensations, 756-759 Thiamin See Vitamin B1 Thickeners See Stabilizers and thickeners Thick filament proteins, 895 Thiobarbituric acid tests, 276-277 Thixotropic flow, 183-184 proteins and, 389-391 Thomson, Thomas, 2, Time-temperature indicators of food quality, 1037-1038 Titanium oxide, 717 Tocopherols, 533 Tomato, biosynthesis of flavor, 990 Toxicants, 825-840 contaminants, 834-838 mycotoxins, 835, 836 definition of, 825-826 evaluating safety, 828-830 formation of toxic compounds in proteins, 402-416 inherent toxicants, 830-834 carcinogens in food, 832 in plants, 831 plant toxicants causing harm, 833 legal aspects, 826-827 public health and, 838-839 terms in food toxicology, 827-828 types of, 825, 826 Tracers, 812, 821 Transferases (enzyme type), 438, 439, 442 Treatise on Adulterations of Food, A (Accum), Triacylglyercols fat substitutes, 803-804 Triacylglycerols, 239, 956-957, 958 autoxidation, 255-259 bleaching, 300 chemistry of frying and, 292-295 consistency, 250-252, 254 deodorization, 300 distribution of fatty acids in fat, 233-239 health and, 312-313 hydrogenation, 300-304 interesterification, 304-307 lipolysis, 254-255 melting behavior, 248-252 mesomorphic phase, 252-254 neutralization, 300 polymorphism and, 243-244 radiolysis, 296-298 safety after frying, 310-311 safety after irradiation, 312 safety of hydrogenated fats, 311 settling and degumming, 300 solid fat index, 249-250 thermal decomposition, 288-292 [Triacylglycerols] See also Fats 2,4,5-Trihydroxybutyrophenone (THBP), 286, 288 Tritium, 22 Tropomyosin, 894-895 Troponin, 894-895 True (protein) digestibility (TD), 400 Tryptophan, oxidation of, 410-411 Tuber proteins, 954 Turmeric, 717 Tyrosine, oxidation of, 412 U Ultraviolet spectrophotometry, 278 Unmodified starches, 196-197 Unsaturated fatty acids, 227-228 Uronic acids, 168 V Vacuum freeze-drying (lyophilization), 79 Van der Walls' forces, 113, 115 protein stability and, 346-347 Vegetable butters, 232-233 Vegetables: effects of processing, 1004-1007 cell disruption, 1005 changes in molecular structure, 1005 chemical changes, 1004 enzyme-catalyzed reactions, 1005 nonenzymic reactions affecting quality, 1004, 1006 flavors in, 738-742 handling and storage, 997-1000 high-temperature injury, 1000 low-temperature injury, 999-1000 mechanical injury, 998 protective substances, 998 stress metabolites, 998, 999 temperature, 998-999 mineral content of, 965 water content of, 19 See also Plant tissues Pag e 1066 Violaxanthin, structure of, 677 Viscosity, role of proteins in, 389-391 Vitamin A, 545-552 assays, 552 bioavailability, 551-552 isomerization, 547-550 source, 545-548, 674-675, 681 stability and degradation modes, 533, 547-551 structure and general properties, 545-547 Vitamin B1, 568-574 assays, 574 bioavailability, 574 stability and degradation modes, 533, 570-574 structure and general properties, 568 Vitamin B2, 574-578 assays, 578 bioavailability, 578 distribution in milk, 577 stability and degradation modes, 575-577 structure and general properties, 574-575 Vitamin B6, 580-589 assays, 589 bioavailability, 588-589 pKa values, 581 sources, 580 stability and degradation modes, 533, 583-588 structure and general properties, 580-582 Vitamin B12, 603-606 assays, 605-606 bioavailability, 605-606 concentration in various foods, 605 stability and degradation modes, 533, 604-606 structure and general properties, 603-604 Vitamin C, 559-568 assays, 567-568 bioavailability, 567 functions in foods, 566-567 reduction potential, 564 sources, 560 [Vitamin C] stability and degradation modes, 533, 561-566 structure and general properties, 559-560 Vitamin D, 552-553 assays, 553 stability, 533 structure and general properties, 552-553 Vitamin E, 553-557 assays, 556-557 bioavailability, 556 concentration in foods, 556 oxidative degradation, 557 stability and degradation mechanism, 554-555 structure and general properties, 553-554 Vitamin K, 557-559 assays, 559 stability and degradation modes, 553, 559 structure and general properties, 557-559 Vitamins, 6, 817-818 analytical methods and sources of data, 537-539 bioavailability, 539 causes of variation/loss in foods, 539-545 definition of, 532-533 dietary recommendations for, 536-537 fat-soluble vitamins, 545-559 fortification of foods, 534-536 in meat, 884 in milk, 872, 873 processing effects, 875-876 optimization of retention, 607-609 effects of packaging, 609 loss prediction, 608-609 thermal processing conditions, 608 in plant tissues, 966 sources of, 534 stability of, 532-533, 536, 537 toxicity, 534 vitamin-like compounds, 606-607 [Vitamins] water-soluble vitamins, 559-606 See also types of vitamins Vitrification, definition of, 87 W Waste management, enzymes in, 512-514 Water, 17-94 abundance of, 18-19 combined methods approach to food stability, 83-84 content of various foods, 19 forms of, 18-19 glossary, 85-87 hydrogen bonding of, 22-23, 24 importance of, 18-19, 85 isotopes of, 21-22 moisture sorption isotherms, 47-51 definition, 48-50 hysteresis, 50-51 temperature dependence, 50 zones, 49-50 molecular association of, 20-24 molecular mobility and food stability, 55-83 physical properties, 19-20 in plant tissues, 945-947 relative vapor pressure and food stability, 52-55 -solute interactions, 30-42 structure of, 29-30 water activity and relative vapor pressure, 42-47 See also Ice Water binding, 30 of proteins, 367-370 Water holding capacity, 30-31 Water-soluble vitamins See Biotin; Folate; Niacin; Pantothenic acid; Vitamin B1; Vitamin B2; Vitamin B6; Vitamin B12; Vitamin C Wax, structure of, 960 Wheat: kernel structure, 970 lipid content of, 958 Wheat flour, 956, 958 Whey proteins, 858-861, 866 Pag e 1067 [Whey proteins] functionality in foods, 870 Wiley, Harvey Washington Williams-Landel-Ferry (WLF) equation, 60, 61, 64, 65 ice recrystallization and, 78 kinetic relevance to food quality, 67, 1022-1023 [Williams-Landel-Ferry (WLF) equation] kinetics during freezing, 73 World Health Organization (WHO), dyes (or lakes) approved by, 652 X Xanthan gum, 184, 208-210 serum cholesterol and, 219 Xanthones, 696, 697 Y Young's equation, 107 Z Zeaxanthin, structure of, 676 Zinc: functions in food, 643 RDAs for, 627 Pag e 1069 About the Editor Owen R Fennema is a Professor of Food Chemistry in the Department of Food Science at the University of Wisconsin—Madison He is coauthor of the books Low Temperature Foods and Living Matter (with William D Powrie and Elmer H Marth) and Principles of Food Science, Part II: Physical Principles of Food Preservation (with Marcus Karel and Daryl B Lund) (both titles, Marcel Dekker, Inc.), and the author or coauthor of over 175 professional papers that reflect his research interests in food chemistry, low-temperature preservation of food and biological matter, the characteristics of water and ice, edible films and coatings, and lipid-fiber interactions A consulting editor for the Food Science and Technology series (Marcel Dekker, Inc.), he is a Fellow of the Institute of Food Technologists and of the Agriculture and Food Chemistry Division of the American Chemical Society, and a member of the American Institute of Nutrition, among other organizations Dr Fennema received the B.S degree (1950) in agriculture from Kansas State University, Manhattan, and the M.S degree (1951) in dairy science and Ph.D degree (1960) in food science and biochemistry from the University of Wisconsin—Madison ... Data Food chemistry / edited by Owen R Fennema — 3rd ed p cm — (Food science and technology) Includes index ISBN 0-8247-9346-3 (cloth : alk paper) — ISBN 0-8247-9691-8 (paper : alk paper) Food Analysis... that often goes unfulfilled by food chemists, is that of helping determine how scientific knowledge is interpreted and used by society Although food chemists and other food scientists should not... years, an acute need has existed for a food chemistry textbook that is suitable for food science students with backgrounds in organic chemistry and biochemistry This book is designed primarily to