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CHAPMAN & HALL/CRC A CRC Press Company Boca Raton London New York Washington, D.C. DICTIONARY of FOOD COMPOUNDS with CD-ROM Edited by SHMUEL YANNAI Additives, Flavors, and Ingredients CAUTION Treat all chemical substances as if they have dangerous properties. The publisher makes no representation, expressed or implied, with regard to the accuracy of the information contained in this Dictionary, and cannot accept any legal responsibility or liability for any errors or omis- sions that may be made. The speciÞc information in this publication on the haz- ardous and toxic properties of certain substances is included to alert the reader to possible dangers associated with the use of these compounds. The absence of such information should not, however, be taken as an indication of safety in use or misuse. This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microÞlming, and recording, or by any information storage or retrieval system, without prior permission in writing from the publisher. The consent of CRC Press LLC does not extend to copying for general distribution, for promotion, for creating new works, or for resale. SpeciÞc permission must be obtained in writing from CRC Press LLC for such copying. Direct all inquiries to CRC Press LLC, 2000 N.W. Corporate Blvd., Boca Raton, Florida 33431. 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Visit the CRC Press Web site at www.crcpress.com © 2004 by Chapman & Hall/CRC No claim to original U.S. Government works International Standard Book Number 1-58488-416-9 Library of Congress Card Number Printed in the United States of America 1 2 3 4 5 6 7 8 9 0 Printed on acid-free paper Library of Congress Cataloging-in-Publication Data Catalog record is available from the Library of Congress iii Table of Contents Preface. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . v Editorial Board . . . . . . . . . . . . . . . . . . . . . . . . vii Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . ix Dictionary Entries A . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 B . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95 C . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145 D . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 237 E . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 427 F. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 487 G . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 519 H . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 589 I . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 741 J. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 779 K . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 785 L . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 793 M. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 815 N. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 957 O. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 985 P . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1037 Q. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1165 R. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1169 S . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1187 T . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1251 U. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1411 V. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1421 W . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1433 X. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1437 Y. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1443 Z . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1445 Name Index . . . . . . . . . . . . . . . . . . . . . . . . 1451 Type of Compound Index . . . . . . . . . . . . . 1620 v Preface For some years, those involved in food chemistry and tech- nology have felt the need for a comprehensive and well- organised reference source documenting the whole range of substances on which they may need information during their day-to-day work. While there are many valuable com- pilations and tabulations of particular areas (e.g., permitted food additives or natural ßavourings), there has been noth- ing available that is truly comprehensive. In addition, the existing reference works have mostly evolved as traditional books, with their associated shortcomings in terms of indexing and expense of updating. With the increasing and sometimes contradictory demands of the consumer market today, the need for the best up-to-date and accurate information has never been greater. This is perhaps not the place to digress into the debate on “Chemicals in Food;” anyone in the position of reading this preface will be quite aware of most of the issues involved, and will have his or her own views. What is certain, however, is that whatever direction one approaches the debate from, it is a sterile and unproductive one unless there is good information about the true state of the science. And that science is of course by no means limited to food technology. Any participant in the debate who is ignorant about the effects of the natural products in the foods we eat is seriously misinformed. Chapman & Hall in its role as a chemical information specialist is uniquely able to provide a technology capable of aiding the compilation and publication of such a com- prehensive reference source. The company's experience in database publishing in chemistry goes back to the late 1970s when compilation of the Þrst electronic edition of the Dictionary of Organic Compounds was begun. Since that time, a series of high-quality searchable data compila- tions has appeared at regular intervals. In due course, it only remained to put this technical expertise together with the specialist knowledge of an experienced international Editorial Board with overall responsibility for content, and a team of contributors with knowledge of particular areas of food components. The resulting Dictionary of Food Compounds is avail- able both in hard copy and electronically as a CD-ROM product. Each has its own advantages. There is nothing to rival the ease of consulting a book version for quick queries and for browsing to get an overall view of the whole Þeld. On the other hand, the electronic version is searchable by chemical substructure as well as text and, for obvious rea- sons, is much more easily updated so that the user can get a very rapid summary of new developments in the science. The Dictionary is aimed not only at food scientists and technologists, but at the wide range of people whose work brings them into contact with the regulatory aspects of food supply and monitoring. The book and CD-ROM versions are complementary. The important thing for the user to be assured of is that the Dictionary of Food Compounds is an ongoing project which the Publishers hope and expect will become a central fea- ture of the information needs of everyone involved in food. Every effort has been taken to ensure the accuracy of the information contained in DFC. Any errors or omissions should be communicated to the Publishers, who will also be pleased to receive any comments about the coverage, and especially suggestions for its expansion. vii Editorial Board EDITOR Prof. Shmuel Yannai Technion-Israel Institute of Technology, Israel EXECUTIVE EDITOR Dr Steven P. Walford Chapman & Hall/CRC, London CONTRIBUTING EDITORS Dr Reto Battaglia Swiss Quality Testing Services Switzerland Dr John Buckingham Consultant Dr Trygve Eklund National Institute of Occupational Health Norway Prof. Jose A. Empis Instituto Nacional de Investigação Agrária e das Pescas, Portugal Dr Pinhas Lindner Agricultural Research Organisation Israel Dr Peter H. Rhodes Consultant Dr Ionel Rosenthal Agricultural Research Organisation Israel Prof. Piotr Tomasik Agricultural Academy of Cracow Poland Dr Terry Ward Consultant ix Introduction Users interested in more detailed factual information on topics outlined below are referred to The Organic Chemist’s Desk Reference (Rhodes, P.A., Chapman & Hall, 1995). 1. USING DFC The arrangement of entries is alphabetical by name. The criteria governing the choice of entry name are described below. Many compounds in DFC are present as derivatives of a parent. The CD-ROM version can be searched by all names given throughout the dictionary, whether entry names, synonyms or derivative names. Every entry is assigned a DFC number to assist ready location. The DFC number consists of a letter of the alpha- bet followed by a number, e.g., A-124. All index entries refer to the DFC number. 2. COMPOUND SELECTION AND PRESENTATION The selection of compounds for DFC is broad. Included are all compounds or group of compounds of interest or potential interest to the food industry in its widest conno- tation. Compounds need not have been exactly deÞned structurally to be included. A full description of the scope of compounds included can be gained by perusing the headings in the Type of Compound Index, since virtually every compound or group of compounds included is listed under at least one of the headings. Printed DFC contains a number of derivatives that are not of direct food interest, but are included because they have been used for chemical characterisation of the main entry compound. However, the number of these is strictly limited. In contrast, the version of an entry on the CD- ROM, where space is not a limitation, is the full version as present on the Chapman & Hall Chemical Database and may include many more derivatives not thought to be of current food interest. When using the CD-ROM, the pos- sibilities for ßexible searching are such that the portion of the entry most relevant to food science can rapidly be homed in on. DFC contains many natural products known to occur in food plants for which no speciÞc food-related informa- tion, such as ßavour or toxicity, appears to be available. In such cases, the decision to include them has been based on the species information given in the entry. If one or more of the species recorded is a food plant or other food source, the compound has been selected for inclusion in the DFC dataset. The label “food plant” is broadly deÞned and includes edible wild foods as well as established crop foods, also toxic plants of potential interest to nutritionists. Where there is some doubt about whether a particular plant is of food signiÞcance, it has generally been included. The sources used to validate food plant information include the CropSEARCH database (http://www.hort.pur- due.edu/newcrop/, Purdue University, US) and the Plants for a Future database (http://www.scs.leeds.ac.uk/pfaf/, Leeds University, UK), and the titles: World Economic Plants — A Standard Reference (Wiersema, J.H. and León, B., CRC Press, 1999); Fenaroli’s Handbook of Flavor Ingredients, 4 th ed., (Burdock, G.A., CRC Press, 2002); Encyclopedia of Food and Color Additives (Burdock, G.A., CRC Press, 1997); Handbook of Nutraceuticals and Func- tional Foods (Wildman, R.E.C., CRC Press, 2000). 3. THE TYPE OF COMPOUND INDEX This is a most important feature of DFC. Every compound of food interest included in the dictionary is indexed under at least one heading, but usually two or more. The headings are of six types. Structural headings (WA) classify naturally occurring food constituents under one of 30 headings according to their chemical structure, such as: WA 1100 — Natural food colourants (betalaines) WA 5100 — Food sugars (disaccharides) Deliberate food additive headings (WC) refer to the various functions performed by such additives, such as: WC 0700 — Antioxidants WC 2100 — Curing agent Food ßavour and odour headings (WE) are self-explan- atory and may refer to natural, nature-identical or synthetic odours and ßavours Food contaminant headings (WG) classify all undesir- able/unintended compounds present in foods, such as: WG 1000 — Animal feed contaminants WG 3500 — Food allergens Food source headings (WI) classify food compounds, both natural and processing-derived, by their food source. Examples are: WI 1000 — Cereals and bakery products WI 6000 — Dairy products Food function headings (WK) are self-explanatory and include for example . temperature scu subcutaneous sepn separation skn skin sl slightly sol soluble soln solution solv solvent sp species (singular) spar sparingly spp species (plural). imprecise items of data; most compounds can be crystallised from several solvent systems and the crystal form often varies. In the case of the small number of