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Food Chemistry

H.-D. Belitz · W. Grosch · P. SchieberleFood Chemistry4th revised and extended ed.With 481 Figures, 923 Formulas and 634 Tables123

Professor Dr. Hans-Dieter Belitz †Professor em. Dr. Werner GroschEhem. apl. Professor für Lebensmittelchemiean der Technischen Universität MünchenEhem. stellvertr. Direktorder Deutschen Forschungsanstaltfür Lebensmittelchemie MünchenLichtenbergstraße85748 GarchingProfessor Dr. Peter SchieberleOrdinarius für Lebensmittelchemiean der Technischen Universität MünchenLeiter des Instituts für Lebensmittelchemiean der Technischen Universität MünchenDirektor der Deutschen Forschungsanstaltfür Lebensmittelchemie MünchenLichtenbergstraße85748 GarchingISBN 978-3-540-69933-0e-ISBN 978-3-540-69934-7DOI 10.1007/978-3-540-69934-7Library of Congress Control Number: 2008931197 Springer-Verlag Berlin Heidelberg 2009This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,broadcasting, reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publication or parts thereof is permitted only under the provisions of the GermanCopyright Law of September 9, 1965, in its current version, and permission for use must alwaysbe obtained from Springer. Violations are liable to prosecution under the German Copyright Law.The use of general descriptive names, registered names, trademarks, etc. in this publication doesnot imply, even in the absence of a specific statement, that such names are exempt from the relevantprotective laws and regulations and therefore free for general use.Production: le-tex publishing services oHG, LeipzigTypesetting: le-tex publishing services oHG, LeipzigCover design: KünkelLopka GmbH, Heidelberg, GermanyPrinted on acid-free paper987654321springer.com

PrefacePreface to the First German EditionThe very rapid development of food chemistry and technology over the last twodecades, which is due to a remarkable increase in the analytical and manufacturingpossibilities, makes the complete lack of a comprehensive, teaching or referencetext particularly noticeable. It is hoped that this textbook of food chemistry willhelp to fill this gap. In writing this volume we were able to draw on our experiencefrom the lectures which we have given, covering various scientific subjects, overthe past fifteen years at the Technical University of Munich.Since a separate treatment of the important food constituents (proteins, lipids, carbohydrates, flavor compounds, etc.) and of the important food groups (milk, meat,eggs, cereals, fruits, vegetables, etc.) has proved successful in our lectures, the subject matter is also organized in the same way in this book.Compounds which are found only in particular foods are discussed where theyplay a distinctive role while food additives and contaminants are treated in theirown chapters. The physical and chemical properties of the important constituentsof foods are discussed in detail where these form the basis for understanding either the reactions which occur, or can be expected to occur, during the production,processing, storage and handling of foods or the methods used in analyzing them.An attempt has also been made to clarify the relationship between the structure andproperties at the level of individual food constituents and at the level of the wholefood system.The book focuses on the chemistry of foodstuffs and does not consider nationalor international food regulations. We have also omitted a broader discussion ofaspects related to the nutritional value, the processing and the toxicology of foods.All of these are an essential part of the training of a food chemist but, because of theextent of the subject matter and the consequent specialization, must today be thesubject of separate books. Nevertheless, for all important foods we have includedbrief discussions of manufacturing processes and their parameters since these areclosely related to the chemical reactions occurring in foods.Commodity and production data of importance to food chemists are mainly givenin tabular form. Each chapter includes some references which are not intendedto form an exhaustive list. No preference or judgement should be inferred from thechoice of references; they are given simply to encourage further reading. Additionalliterature of a more general nature is given at the end of the book.This book is primarily aimed both at students of food and general chemistry butalso at those students of other disciplines who are required or choose to study foodchemistry as a supplementary subject. We also hope that this comprehensive text

viPrefacewill prove useful to both food chemists and chemists who have completed theirformal education.We thank sincerely Mrs. A. Mödl (food chemist), Mrs. R. Berger, Mrs. I. Hofmeier,Mrs. E. Hortig, Mrs. F. Lynen and Mrs. K. Wüst for their help during the preparation of the manuscript and its proofreading. We are very grateful to Springer Verlagfor their consideration of our wishes and for the agreeable cooperation.Garching,July 1982H.-D. BelitzW. GroschPreface to the Fourth English EditionThe fourth edition of the “Food Chemistry” textbook is a translation of the sixthGerman edition of this textbook. It follows a general concept as detailed in thepreface to the first edition given below. All chapters have been carefully checkedand updated with respect to the latest developments, if required. Comprehensivechanges have been made in Chapters 9 (Contaminants), 18 (Phenolic Compounds),20 (Alcoholic Beverages) and 21 (Tea, Cocoa). The following topics were newlyadded: the detection of BSE and D-amino acids,the formation and occurrence of acrylamide and furan,compounds having a cooling effect,technologically important milk enzymes,the lipoproteins of egg yolk,the structure of the muscle and meat aging,food allergies,the baking process,the reactivity of oxygen species in foods,phytosterols,glycemic index,the composition of aromas was extended: odorants (pineapple, raw and cookedmutton, black tea, cocoa powder, whisky) and taste compounds (black tea,roasted cocoa, coffee drink).The production data for the year 2006 were taken from the FAO via Internet. Thevolume of the book was not changed during the revision as some existing chapterswere shortened.We are very grateful to Dr. Margaret Burghagen for translating the manuscript. Itwas our pleasure to collaborate with her.We would also like to thank Prof. Dr. Jürgen Weder and Dr. Rolf Kieffer for severalvaluable recommendations. We are also grateful to Sabine Bijewitz and Rita Jaukerfor assistance in completing the manuscript, and Christel Hoffmann for help withthe literature and the index.Garching,Mai 2008W. GroschP. Schieberle

3.50.4Water . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Foreword . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Water Molecule . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Liquid Water and Ice . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Effect on Storage Life . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Water Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Water Activity as an Indicator . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Phase Transition of Foods Containing Water . . . . . . . . . . . . . . . . .WLF Equation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .7Amino Acids, Peptides, Proteins . . . . . . . . . . . . . . . . . . . . . . . . .Foreword . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Amino Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .General Remarks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Classification, Discovery and Occurrence . . . . . . . . . . . . . . . . . . .Classification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Discovery and Occurrence . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Physical Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Dissociation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Configuration and Optical Activity . . . . . . . . . . . . . . . . . . . . . . . . .Solubility . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .UV-Absorption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Chemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Esterification of Carboxyl Groups . . . . . . . . . . . . . . . . . . . . . . . . . .Reactions of Amino Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Acylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Alkylation and Arylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Carbamoyl and Thiocarbamoyl Derivatives . . . . . . . . . . . . . . . . . .Reactions with Carbonyl Compounds . . . . . . . . . . . . . . . . . . . . . . .Reactions Involving Other Functional Groups . . . . . . . . . . . . . . . .Lysine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Arginine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Aspartic and Glutamic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Serine and Threonine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Cysteine and Cystine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Methionine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Tyrosine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .88889991212131415161616161820212223232324242424

eactions of Amino Acids at Higher Temperatures . . . . . . . . . . .Acrylamide . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Mutagenic Heterocyclic Compounds . . . . . . . . . . . . . . . . . . . . . . .Synthetic Amino Acids Utilized for Increasingthe Biological Value of Food (Food Fortification) . . . . . . . . . . . . .Glutamic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Aspartic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Lysine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Methionine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Phenylalanine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Threonine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Tryptophan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Sensory Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Peptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .General Remarks, Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . . .Physical Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Dissociation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Sensory Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Individual Peptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Glutathione . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Carnosine, Anserine and Balenine . . . . . . . . . . . . . . . . . . . . . . . . .Nisin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Lysine Peptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Other Peptides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Amino Acid Sequence . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Amino Acid Composition, Subunits . . . . . . . . . . . . . . . . . . . . . . . .Terminal Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Partial Hydrolysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Sequence Analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Derivation of Amino Acid Sequencefrom the Nucleotide Sequence of the Coding Gene . . . . . . . . . . .Conformation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Extended Peptide Chains . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Secondary Structure (Regular Structural Elements) . . . . . . . . . . .β -Sheet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Helical Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Reverse Turns . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Super-Secondary Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Tertiary and Quaternary Structures . . . . . . . . . . . . . . . . . . . . . . . . .Fibrous Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Globular Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .BSE . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Quaternary Structures . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Denaturation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Physical Properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Dissociation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Optical Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Solubility, Hydration and Swelling Power . . . . . . . . . . . . . . . . . . .Foam Formation and Foam Stabilization . . . . . . . . . . . . . . . . . . . .Gel Formation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1414243444648484950515252535353555656585860606262

4.7.3.11.4.7.3.21.5Emulsifying Effect . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Chemical Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Lysine Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Reactions Which Retain the Positive Charge . . . . . . . . . . . . . . . . .Reactions Resulting in a Loss of Positive Charge . . . . . . . . . . . . .Reactions Resulting in a Negative Charge . . . . . . . . . . . . . . . . . . .Reversible Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Arginine Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Glutamic and Aspartic Acid Residues . . . . . . . . . . . . . . . . . . . . . .Cystine Residue (cf. also Section 1.2.4.3.5) . . . . . . . . . . . . . . . . . .Cysteine Residue (cf. also Section 1.2.4.3.5) . . . . . . . . . . . . . . . . .Methionine Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Histidine Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Tryptophan Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Tyrosine Residue . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Bifunctional Reagents . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Reactions Involved in Food Processing . . . . . . . . . . . . . . . . . . . . .Enzyme-Catalyzed Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Foreword . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Proteolytic Enzymes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Serine Endopeptidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Cysteine Endopeptidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Metalo Peptidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Aspartic Endopeptidases . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Chemical and Enzymatic Reactionsof Interest to Food Processing . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Foreword . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Chemical Modification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Acylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Alkylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Redox Reactions Involving Cysteine and Cystine . . . . . . . . . . . . .Enzymatic Modification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Dephosphorylation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Plastein Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Cross-Linking . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Texturized Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Foreword . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Starting Material . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Texturization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Spin Process . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .Extrusion Process . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .63646464656566666767686969707070707474

The very rapid development of food chemistry and technology over the last two decades, which is due to a remarkable increase in the analytical and manufacturing possibilities, makes the complete lack of a comprehensive, teaching or reference text particularly noticeable. It is hoped that this textbook of food chemistry will help to fill this gap.

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Food Fraud and "Economically Motivated Adulteration" of Food and Food Ingredients Congressional Research Service 1 Background Food fraud, or the act of defrauding buyers of food and food ingredients for economic gain— whether they be consumers or food manufacturers, retailers, and importers—has vexed the food industry throughout history.

Introductory Food Chemistry, John W. Brady, Cornell University Press, 2013 Principles of Food Chemistry, 3rd Edition (J.M. deMan), Springer Science, NY. 1999 Crystallization and solidification properties of lipids, Neil Widlak; Richard W

11 I Blue Link User’s Manual Blue Link User’s Manual I 12 Using Blue Link in Your Car Standard Rearview Mirror Controls for Blue Link in-vehicle voice-response use are located on the rearview mirror. Press the Blue Link button for access to the voice-response menu of services: Service Link Roadside Assistance Blue Link Account Assistance

presents the rudiments of a satellite link design in a tutorial form with numerical examples. Index Term—Satellite communications, Link analysis, Link design, EIRP, SNR, CNR. I. INTRODUCTION The satellite link is essentially a radio relay link, much like the terrestrial microwave radio relay link with the singular

ALBERT WOODFOX . CIVIL ACTION NO. 06-789-JJB-RLB . VERSUS . BURL CAIN, WARDEN OF THE LOUISIANA . STATE PENITENTIARY, ET AL. RULING . Before this Court is the pending Motion (doc. 279) for Rule 23(c) release of Petitioner, Albert Woodfox. Briefs were filed in response to this motion and were considered by this Court. Subsequently, a motion hearing on this matter was held before this Court on .