SECOND EDITION FLAVOR CHEMISTRY and TECHNOLOGY © 2006 by Taylor & Francis Group, LLC SECOND EDITION FLAVOR CHEMISTRY and TECHNOLOGY GARY REINECCIUS Boca Raton London New York Singapore A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc. © 2006 by Taylor & Francis Group, LLC TX69337_Discl.fm Page 1 Tuesday, June 7, 2005 8:29 AM Published in 2006 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2006 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10987654321 International Standard Book Number-10: 1-56676-933-7 (Hardcover) International Standard Book Number-13: 978-1-56676-933-4 (Hardcover) Library of Congress Card Number 2005041778 This book contains information obtained from authentic and highly regarded sources. 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For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Reineccius, Gary. Flavor chemistry and technology – 2nd ed. / Gary Reineccius. p. cm. Includes bibliographical references and index. ISBN 1-56676-933-7 1. Flavor. 2. Flavoring essences. I. Title. TP372.5.R374 2005 664¢.5—dc22 2005041778 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com Taylor & Francis Group and the CRC Press Web site at is the Academic Division of T&F Informa plc. http://www.crcpress.com © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page v Thursday, May 19, 2005 9:15 AM Dedication To my teachers © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page vii Thursday, May 19, 2005 9:15 AM Preface This book combines the essentials of both flavor chemistry and flavor technology. Modern flavor chemistry as an academic area of study has existed for over 40 years. The advent of gas chromatography in the early 1960s (rapidly coupled with mass spectrometry) heralded the beginning of this research area. These instruments gave scientists the ability to separate and identify the host of volatiles found in our foods that contribute to the aroma of foods. Flavor chemistry flourished in the U.S., Europe, and Japan in the late 1960s and early 1970s. Since money was readily available for flavor research, great strides were made in understanding the biosynthetic pathways of flavor formation and the chemical constituents that are important to flavor. Government support for flavor research in the U.S. started to decline in the early 1980s and stabilized at a level that has permitted a limited number of laboratories to exist. Fortunately, flavor research in Europe has continued to be funded, and Europe has become the leader in flavor research. In recent years, the food industry and various commodity groups such as the dairy industry have come to recognize the value of flavor to the consumer and have provided increasing support to the academic community in the U.S. Thus, we find a growth in flavor research once again in the U.S. Our journey of understanding has taken us from providing long lists of volatile chemicals found in foods (thought to be the way to replicate nature), to studies to determine the key volatile compounds, to studies on food/aroma interactions, flavor release, and most recently, to taste, perception, and cognitive functioning. It is unlikely that this is the final frontier — for we thought we were there nearly 40 years ago! Nature is not readily giving up its secrets to flavor and the pleasure it provides in our daily lives. Flavor technology is an ancient area of study. Man has searched for a means of making food more pleasurable or palatable since time began. The flavor industry had its beginnings with the search for, and trading of, spices many centuries ago. This searching and trading has been responsible for the discovery of new worlds. Today this industry is nearly invisible to the average consumer since only a few members of the industry sell directly to the consumer: most are ingredient suppliers only known to their client companies who interface with the ultimate consumer. The flavor industry today has a world market of approximately 16.3 billion dollars (www.Leffingwell.com). The total global sales are only somewhat larger than a single major food company. The flavor industry is comprised of a few large companies and a host of small companies (perhaps 500+). There is little published about today’s flavor industry because of its highly competitive and secretive nature. It is difficult and sometimes impossible to protect a flavoring via patents, so flavoring materials, synthetic chemicals, and manufacturing procedures are kept secret to avoid supporting competitive companies. © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page viii Thursday, May 19, 2005 9:15 AM The author has used the best information available to try to give a view of this industry. Often patents or personal experience have been called on due to a dearth of public information on the industry. While only a sampling of the literature available could be included in many areas, the author has provided abundant refer- encing to provide direction for the reader. This book is intended to serve as a suitable text for both undergraduate and graduate level courses as well as a reference text for those in academia or industry. © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page ix Thursday, May 19, 2005 9:15 AM Acknowledgments I wish to acknowledge the host of individuals referenced in this text for their efforts to provide understanding to a field that is ever so slowly giving up its secrets. I wish to thank my many teachers for sharing their knowledge and helping me down a career path that has been most challenging and exciting. I have to thank my students also for educating me in their specific research topics — I am certain they taught me more than I taught them. I will forever be in debt to Henry Heath for what he has given to the field and to me personally through his writing. Several sections of this book still reflect his contributions. © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page xi Thursday, May 19, 2005 9:15 AM The Author Gary Reineccius, Ph.D., is a professor in the Department of Food Science and Nutrition at the University of Minnesota. He has been actively involved in flavor research for more than 35 years. During this time he has published over 190 research articles. Dr. Reineccius has spent sabbatical leaves with Fritzsche Dodge and Olcott (New York, flavor creation and production), Nestle (Switzerland, reaction flavors), and most recently Robertet S.A. (France, taste modifiers and manufacturing). Dr. Reineccius teaches courses in Chemical and Instrumental Analysis of Foods, Food Processing, and Flavor Chemistry and Technology. He has written a college textbook on food flavors with Henry Heath. This was the first textbook in the flavor area that combined both flavor chemistry and technology. Dr. Sara Risch and he edited and were major contributors to two books on flavor encapsulation. He is the editor of the Source Book of Flavors and an ACS symposium proceeding titled “Heteroatomic Aroma Compounds.” Dr. Reineccius’ achievements have been recognized by several local and inter- national organizations. He is an honorary member of the Society of Flavor Chemists. He has been granted the Palmer Award for his contribution to chromatography by the Minnesota Chromatography Forum. He has received the Distinguished Achieve- ment and Service in Agricultural and Food Chemistry Award from the American Chemical Society and been presented the Stephen S. Chang Award by the Institute of Food Technologists. These are the highest awards given to individuals in the flavor area. He is a Fellow of the American Chemical Society. He often speaks at public schools and other groups. His favorite lay topics are chocolate (he spent three years researching chocolate flavor for his Ph.D. thesis) and the chemistry of gourmet cooking. From a professional standpoint, his favorite topic is flavor encapsulation. He has been actively engaged in research in this area since 1964. © 2006 by Taylor & Francis Group, LLC TX69337_book.fm Page xiii Thursday, May 19, 2005 9:15 AM Contents PART I Flavor Chemistry.......................................... 1 Chapter 1 An