《食品化学》课程教学资源（书籍文献）Food Chemistry，Edited by Owen R. Fennema，Third Edition

PageiFood ChemistryThirdEditionEdited byOwen R.FennemaUniversity of Wisconsin-MadisonMadison,WisconsinMARGELDEXKERMARCEL DEKKER,INCNEWYORK·BASEL·HONGKONG

Pag e i Food Chemistry Third Edition Edited by Owen R. Fennema University of Wisconsin￾Madison Madison, Wisconsin MARCEL DEKKER, INC. NEW YORK • BASEL • HONG KONG

PageiiPrefacetotheThirdEditionMore than a decade has passed since the publication ofthe second edition of Food Chemistry, so the appropriateness of anupdated version should be apparent. The purposes of the book remain unchanged: it is primarily a textbook for upper divisionundergraduates and beginning graduate students who have sound backgrounds in organic chemistry and biochemistry,and issecondarily a reference book. Information on food analysis is intentionally absent, except where its presence fits logically withthe topic under discussion. As a textbook for undergraduates, it is designed to serve as the basis of a two-semester course onfood chemistry with the assumption that the instructor will make selective reading assignments as deemed appropriate. Individualchapters 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 aretotallynew.These cover such topics as proteins, dispersions,enzymes, vitamins, minerals,animal tissues,toxicants, andpigments. Chapters by contributors to the second edition have been thoroughly revised. For example, in the chapter “Water andIce,amajoradditiondealswithmolecularmobilityandglasstransitionphenomena.Theresult isabookthatismorethan6o%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 wasaccomplished in the chapters“Lipids,"“Proteins,” and “Carbohydrates,” and minerals were covered in the chapter "Vitaminsand Minerals." Although this was organizationally sound, the result was superficial treatment of dispersions and minerals. Thenew chapters on these topics provide depth of coverage that is more consistent with the remainder of the book. Associated withthesechangesisa chapter,writtenbyanewcontributor,that is nowdevoted solelytovitamins.Itismybeliefthatthischapterrepresentsthefirstcomplete,in-depthtreatiseonvitaminswithanemphasisonfoodchemistryI would be remiss not to thank the contributors for their hard work and tolerance of my sometimes severe editorial oversight.Theyhaveproduced abookthat isoffirst-ratequality.Aftertwentyyearsandtwoprevious editions,I amfinallysatisfied thatallmajor topics are covered appropriately with regard to breadth and depth of coverage, and that a proper focus on reactionspertaining specifically to foods has been achieved.This focus successfully dis-

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-

Pageivtinguishes food chemistry from biochemistry in the same sense that biochemistry is distinct from, yet still dependent on, organicchemistry,Although I have planned and edited this edition with great care, minor errors are inevitable, especially in the first printing, If theseare discovered, I would very much appreciate hearing from you so that corrections can be effected promptlyOWENR.FENNEMA

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

PageixContents三Preface to the Third EditionPrefaceto theSecond EditionYviPreface to the First EditionxiContributors11. Introduction to Food ChemistryOwen R. Fennema and Steven R. Tannenbaum172. Water and IceOwen RFennema953.Dispersed Systems: Basic ConsiderationsPieter Walstra1574.CarbohydratesJames N. BeMiller and Roy L. Whistler2255. LipidsWassef W.Nawar3216. Amino Acids, Peptides, and ProteinsSrinivasanDamodaran4317. EnzymesJohnR.Whitaker5318. VitaminsJesse F.Gregory III6179. MineralsDennisD.Miller

Page ix Contents Preface to the Third Edition iii Preface to the Second Edition v Preface to the First Edition vii Contributors xi 1. Introduction to Food Chemistry Owen R. Fennema and Steven R. Tannenbaum 1 2. Water and Ice Owen R. Fennema 17 3. Dispersed Systems: Basic Considerations Pieter Walstra 95 4. Carbohydrates James N. BeMiller and Roy L. Whistler 157 5. Lipids Wassef W. Nawar 225 6. Amino Acids, Peptides, and Proteins Srinivasan Damodaran 321 7. Enzymes John R. Whitaker 431 8. Vitamins Jesse F. Gregory III 531 9. Minerals Dennis D. Miller 617

PagevPrefacetotheSecondEditionConsiderable time has passed since publication ofthefavorably received first edition so a new edition seems appropriate.Thepurpose ofthe book remains unchangedit is intended to serve as a textbook for upper division undergraduates or beginninggraduate students who have sound backgrounds in organic chemistry and biochemistry, and to provide insight to researchersinterested in food chemistry. Although the book is most suitable for a two-semester course on food chemistry, it can be adaptedto a one-semester course by specifying selective reading assignments. It should also be noted that several chapters are ofsufficientlengthanddepthtobeusefulasprimarysourcematerialsforgraduate-levelspecialtycourses.This edition has the same organization as the first, but differs substantially in other ways. The chapters on carbohydrates, lipidsproteins, flavors, and milk and the concluding chapter have new authors and are, therefore, entirely new. The chapter on fooddispersions has been deleted and the material distributed at appropriate locations in other chapters. The remaining chapters,withoutexception,havebeensubstantiallymodified,andtheindexhasbeengreatlyexpanded,includingtheadditionofachemical index.Furthermore,this edition, incontrasttothefirst, ismoreheavily weighted inthe directionof subject matterthat isunique to food chemistry, i.e.,there is less overlap with materials covered in standard biochemistry courses. Thus the book hasundergone major remodeling and refinement, and I am indebted to the various authors for their fine contributions and for theirtoleranceofmysometimessevereeditorial guidance.This book, in my opinion, provides comprehensive coverage of the subject of food chemistry with the same depth andthoroughnessthat ischaracteristicofthebetterquality introductorytextbooksonorganicchemistryand biochemistry.This,Ibelieve, is a significant achievement that reflects a desirable maturation of the field of food chemistry.OWENR.FENNEMA

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

PageviiPreface to the First EditionFor many years, an acute need has existed for a food chemistry textbook that is suitable for food science students withbackgroundsinorganicchemistryandbiochemistry.Thisbook isdesignedprimarilytofilltheaforementioned need,andsecondarily,to serve as a reference sourceforpersons 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 authorsfor 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 deemednecessary to enable the many facets of food chemistry to be covered at a depth adequate for the primary audience. Since I amacutely aware ofthe above pitfalls, care has been taken to minimize them, and I believe the end product, considering it is a firstedition, is really quite satisfyingexcept perhaps for the somewhat generous length. If the readers concur with my judgment, Iwill be pleased but unsurprised, since a book prepared by such outstanding personnel can hardly fail, unless of course the editormismanages the talent.Organization of the book is quite simple and I hope appropriate. Covered in sequence are major constituents of food, minorconstituents offood, food dispersions, edible animal tissues, edible fluids of animal origin, edible plant tissues and interactionsamongfoodconstituentstheintentbeingtoprogressfromsimpletomorecomplexsystems.Completecoverageofallaspectsoffood chemistry,ofcourse,has not been attempted.It is hoped, however,that the topics ofgreatest importance havebeentreated adequately.In order to help achievethis objective,emphasis has been given tobroadlybased principles that apply tomany foods.Figures and tables have been used liberally in the belief that this approach facilitates understanding of the subject matterpresented.The number ofreferences cited should be adequate to permit easy access to additional information.To all readers Iextend an invitation to report errors that no doubt have escaped my attention, and to offer suggestions forimprovements that can be incorporated in future (hopefuly) editions.Sinceenjoyment is an unlikelyreaderresponsetothisbook,thebestIcanhopefor isthatreaderswillfind itenlighteningandwell suited for its intended purposeOWENR.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

Pagex10.Colorants651J.H.vonElbeand Steven J.Schwartz72311. FlavorsRobert C. Lindsay76712. Food AdditivesRobert C. Lindsay82513.Toxic SubstancesMichael W. Pariza84114.Characteristicsof MilkHarold E. Swaisgood87915.CharacteristicsofEdibleMuscleTissuesE.Allen Foegeding,Tyre C.Lanier, and Herbert O.Hultin94316. Characteristics of Edible Plant TissuesNorman F. Haard and Grady W. Chism101317. Summary: Integrative ConceptsPetros Taoukis and Theodore P. LabuzaAppendices1043A.Intenational SystemofUnits(SI),TheModernized MetricSystem1047B.ConversionFactors(Non-SI UnitstoSIUnits)1048C. Greek Alphabet1051Index

Page 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

PagexiContributorsJames N. BeMiller Department of Food Science, Purdue University, West Lafayette, IndianaGrady W. Chism Department of Food Science and Technology, The Ohio State University, Columbus, OhioSrinivasan Damodaran Department of Food Science, University of WisconsinMadison, Madison, WisconsinOwen R.FennemaDepartmentofFood Science,University ofWisconsinMadison,Madison,WisconsinE. Allen Foegeding Department ofFood Science, North Carolina State University, Raleigh, North CarolinaJesse F. Gregory III Department ofFood Science and Human Nutrition, University ofFlorida, Gainesville, FloridaNorman F.Haard Department ofFood Science and Technology, Institute of Marine Resources, University ofCaliforniaDavis,CaliforniaHerbert O. Hultin Department ofFood Science, University of Massachusetts, Amherst, MassachusettsTheodore P.Labuza Department ofFood Science and Nutrition, University of Minnesota, St. Paul, MinnesotaTyre C. Lanier Department of Food Science, North Carolina State University, Raleigh, North CarolinaRobert C. Lindsay Department of Food Science, University of WisconsinMadison, Madison, WisconsinDennis D. Miller Department of Food Science, Cornell University, Ithaca, New York

Page 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

PagexiWassef W.NawarDepartment ofFood Science,University of Massachusetts, Amherst, MassachusettsMichael W.Pariza Department of Food Microbiology and Toxicology,Food Research Institute, University ofWisconsinMadison, Madison, WisconsinSteven J. Schwartz Department of Food Science, North Carolina State University, Raleigh, North CarolinaHarold E.Swaisgood Department ofFood Science, North Carolina State University,Raleigh, North CarolinaSteven R. Tannenbaum Department ofChemistry,Division of Toxicology, Massachusets Institute of TechnologyCambridge,MassachusettsPetros Taoukis Department ofChemical Engineering,National Technical University ofAthens, Athens, GreeceJ.H.von ElbeDepartment ofFood Science,University of WisconsinMadison, Madison,WisconsinPieter Walstra Department ofFood Science, Wageningen Agricultural University, Wageningen, The NetherlandsRoy L.Whistler Department of Biochemistry,Purdue University, West Lafayette, IndianaJohn R. Whitaker Department ofFood Science and Technology, University of California, Davis, California*PresentafiliatioiheOhio StateUniversity,Columbus,Ohio

Page 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

Pagel1IntroductiontoFood ChemistryOwenRFennemaUniversityofWisconsinMadison,Madison,WisconsinSteven R. TannenbaumMassachusetts Institute of Technology, Cambridge, Massachusetts11.1.What Is Food Chemistry?21.2. History of Food Chemistry11.3. Approach to the Study of Food Chemistry11.3.1. Quality and Safety Attributes71.3.2.Chemical and Biochemical Reactions11.3.3. Effect of Reactions on the Quality and Safety of Food101.3.4. Analysis of Situations Encountered During the Storage andProcessing of Food131.4. Societal Role of Food Chemists131.4.1.Why ShouldFood ChemistsBecome Involved in SocietalIssues?131.4.2. Types of Involvement15References1.1 What is Food Chemistry?Concern aboutfood existsthroughouttheworld,buttheaspectsofconcern differwithlocation.Inunderdevelopedregionsoftheworld,thebulk ofthepopulation isinvolved infoodproduction,yetattainmentof adequateamountsandkindsofbasicnutrients remains an ever-present problem. In developed regions of the world, food production is highly mechanized and only asmallfraction ofthepopulation is involved in this activity.Food is available in abundance,much of it is processed,andtheuseofchemical additives is common. In thesefortunate localities, concems about food relate mainly to cost, quality, variety,convenience,andtheeffects of processingand added chemicals on wholesomeness and nutritivevalue.Alloftheseconcernsfallwithin the realm offood sciencea science that deals with the physical, chemical, and biological properties offoods as theyrelate to stability, cost, quality, processing, safety, nutritive value, wholesomeness, and convenience.Food science is an interdisciplinary subject involving primarily bacteriology,chemistry

Pag e 1 1 Introduction to Food Chemistry Owen R. Fennema University of Wisconsin—Madison, Madison, Wisconsin Steven R. Tannenbaum Massachusetts Institute of Technology, Cambridge, Massachusetts 1.1. What Is Food Chemistry? 1 1.2. History of Food Chemistry 2 1.3. Approach to the Study of Food Chemistry 7 1.3.1. Quality and Safety Attributes 7 1.3.2. Chemical and Biochemical Reactions 7 1.3.3. Effect of Reactions on the Quality and Safety of Food 7 1.3.4. Analysis of Situations Encountered During the Storage and Processing of Food 10 1.4. Societal Role of Food Chemists 13 1.4.1. Why Should Food Chemists Become Involved in Societal Issues? 13 1.4.2. Types of Involvement 13 References 15 1.1 What is Food Chemistry? Concern about food exists throughout the world, but the aspects of concern differ with location. In underdeveloped regions of the world, the bulk of the population is involved in food production, yet attainment of adequate amounts and kinds of basic nutrients remains an ever-present problem. In developed regions of the world, food production is highly mechanized and only a small fraction of the population is involved in this activity. Food is available in abundance, much of it is processed, and the use of chemical additives is common. In these fortunate localities, concerns about food relate mainly to cost, quality, variety, convenience, and the effects of processing and added chemicals on wholesomeness and nutritive value. All of these concerns fall within the realm of food science—a science that deals with the physical, chemical, and biological properties of foods as they relate to stability, cost, quality, processing, safety, nutritive value, wholesomeness, and convenience. Food science is an interdisciplinary subject involving primarily bacteriology, chemistry