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Perspectives in Flavor and Fragrance Research Perspectives in Flavor and Fragrance Research. Edited by Philip Kraft and Karl A. D. Swift © Verlag Helvetica Chimica Acta AG, Postfach, CH•8042 Zürich, Switzerlannd, 2005 Perspectives in Flavor and Fragrance Research Philip Kraft, Karl A. D. Swift (Eds.) Verlag Helvetica Chimica Acta · Zürich Dr. Philip Kraft Givaudan Schweiz AG Überlandstrasse 138 CH-8600 Dübendorf Switzerland Dr. Karl A. D. Swift Maybridge Ltd. Trevillett, Tintagel Cornwall PL34 0HW United Kingdom This book was carefully produced. Nevertheless, editor and publishers do not warrant the information contained therein to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details, or other items may inadvertently be inaccurate. Published jointly by VHCA, Verlag Helvetica Chimica Acta AG, Zürich (Switzerland) WILEY-VCH, GmbH & Co. KGaA, Weinheim (Federal Republic of Germany) Production Manager: Bernhard Rügemer Cover Design: Philip Kraft Library of Congress Card No. applied for. A CIP catalogue record for this book is available from the British Library. Die Deutsche Bibliothek – CIP-Cataloguing-in-Publication-Data A catalogue record for this publication is available from Die Deutschen Bibliothek ISBN 3-906390-36-5 © Verlag Helvetica Chimica Acta AG, Postfach, CH–8042 Zürich, Switzerland, 2005 Printed on acid-free paper. All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Printing: Konrad Triltsch, Print und digitale Medien, D-97199 Ochsenfurt-Hohestadt Printed in Germany Preface What began as an annual one-day event in the late 1980×s, the −Flavor & Fragrance× conference of the Royal Society of Chemistry and the Society of Chemical Industry has grown into the multi-day international meeting it is today. Since the −International Congresses of Flavors, Fragrances and Essential Oils× were discontinued after the Istanbul ICEOFF in 1995, the −Flavor & Fragrance× conference of the RSC and SCI constitutes the only international forum for both flavor and fragrance chemists. Both flavor and fragrance chemistry continue to be rapidly growing domains fueled by the constant demand for innovation and the ever-changing trends in the F&F industry. Previous meetings held in 1997 and 2001 had their respective presentations published in proceedings books. The −F&F 2004× meeting held 12th ± 14th May at the UMIST Conference Centre, Manchester, is the subject of this proceedings book, which continues the series. This proceedings book contains 18 of the 24 presentations, the majority of which has also appeared in a special issue of Chemistry & Biodiversity dedicated to this conference. Four chapters are devoted to natural-product chemistry, two relate to the biochemistry of olfaction and malodor production, three to foods and flavors, and nine cover the many aspects of fragrance chemistry. The book is directed primarily towards anyone who works in an R&D environment within the flavor and fragrance industry and to academic researchers interested in this field. As most of the chapters have a review-like character, it may, however, also be used as an advanced textbook to complement an introductory work such as −Chemistry and Technology of Flavors and Fragrances×, Ed. D. Rowe, Blackwell Publishing, Oxford, 2005. But our primary aim is to promote this exciting area of science and keep it visible to a wider scientific community. The logo of the conference, also shown on the cover of this book, features Ambrocenide¾, a new powerful ambery odorant that emerged from classical cedrene chemistry. It should symbolize the endless possibilities in the search for new aroma chemicals, even in the −well-explored× areas of terpene-derived materials or ambery odorants, and the strong momentum of this industry in general. We plan to highlight a different new odorant in the logo of the conference every three years, each time from a different company. In September 2007, the next flavor and fragrance conference will take place at the Imperial College in London, England. This event promises to be an exciting occasion and will have an equally impressive line up of prominent academics and industrialists. Please check the following website for future plans as they evolve: www.confsec.co.uk. The editors would like to express their sincere thanks to all the contributors who painstakingly transformed their respective presentations into the manuscripts found in this book. Our thanks also go to all the speakers and delegates at the 2004 conference, the conference secretariat, and to the RSC and SCI for their continued financial VI PREFACE backing of the event. Finally, we would like to express our gratitude to Dr. M. Volkan Kısak¸rek and Dr. Richard J. Smith of the Verlag Helvetica Chimica Acta for their help in preparing this book, and for their enthusiasm for the project overall. February 2005 Philip Kraft Karl A. D. Swift Contents Molecular and Cellular Basis of Human Olfaction H. Hatt 1 Vanishing Flora ± Lost Chemistry: The Scents of Endangered Plants around the World R. Kaiser 15 From the Linden Flower to Linden Honey ± Volatile Constituents of Linden Nectar, the Extract of Bee-Stomach and Ripe Honey R. Naef*, A. Jaquier, A. Velluz, B. Bachofen 31 Pyrazines and Pyridines from Black Pepper Oil (Piper nigrum L.) and Haitian Vetiver Oil (Vetiveria zizanioides (L.) Nash) R. A. Clery,* Christopher J. Hammond, A. C. Wright 41 14-Methylpentadecano-15-lactone (Muscolide): A New Macrocyclic Lac- tone from the Oil of Angelica archangelica L. D. Lopes, H. Strobl, P. Kolodziejczyk* 47 Odor and (Bio)diversity: Single Enantiomers of Chiral Fragrant Substances A. Abate, E. Brenna*, C. Fuganti, F. G. Gatti, S. Serra 55 Scent through the Looking Glass C. S. Sell 67 Silylating Reagents: A Powerful Tool for the Construction of Isosteric Analogs of Highly Branched Odorants L. Doszczak, T. Gasperi, A. Saint-Dizier, M. A. Loreto, and D. Enders* 89 VIII CONTENTS New Woody and Ambery Notes from Cedarwood and Turpentine Oil J. Panten*, H.-J. Bertram, H. Surburg 105 A Novel Approach to Prezizaane Sesquiterpenes A. Goeke*, D. Mertl, G. Brunner 119 −Brain Aided× Musk Design P. Kraft 127 New Alicyclic Musks: The Fourth Generation of Musk Odorants M. Eh 145 New Macrocyclic Musk Compounds H. Matsuda*, S. Watanabe, K. Yamamoto 155 The Search for New Fragrance Ingredients for Functional Perfumery A. P. S. Narula 163 Binding Studies and Computer-Aided Modelling of Macromolecule/ Odorant Interactions H. Guth*, R. Fritzler 173 Studies on the Volatile Compounds of Roasted Spotted Shrimp T. Tachihara, S. Ishizaki, M. Ishikawa, T. Kitahara* 197 Fun with Furans D. Rowe 207 Identification of New Odoriferous Compounds in Human Axillary Sweat Y. Hasegawa*, M. Yabuki, M. Matsukane 215 PERSPECTIVES IN FLAVOR AND FRAGRANCE RESEARCH 1 Molecular and Cellular Basis of Human Olfaction by Hanns Hatt Ruhr-Universit‰t Bochum, Lehrstuhl f¸r Zellphysiologie, Universit‰tsstrasse 150, D-44801 Bochum (phone: 49 23432 24586; e-mail: [email protected]) The human olfactory systems recognize and discriminate a large number of different odorant molecules. The detection of chemically distinct odorants begins with the binding of an odorant ligand to a specific receptor protein in the ciliary membrane of olfactory neurons. To address the problem of olfactory perception at a molecular level, we have cloned, functionally expressed, and characterized some of the human olfactory receptors from chromosome 17. Our results show that a receptor protein is capable of recognizing the particular chemical substructure of an odor molecule and, therefore, is able to respond only to odorants that have a defined molecular structure. These findings represent the beginning of the molecular understanding of odorant recognition in humans. In the future, this knowledge could be used for the design of synthetic ideal receptors for specific odors (biosensors), or the perfect odor molecule for a given receptor. Introduction. ± Even if we have lost faith in our noses, we are still strongly influenced by smells, even if only subconsciously. Smells can evoke memories and emotions, influence our mood, and are important for our enjoyment when eating. We often use the word taste erroneously, when we actually mean smell; for we can only taste something if it is salty, sour, sweet or bitter. With closed eyes and nose, we can maximally discriminate between a sweet banana and a sour cucumber. All the delicate nuances of an epicurean cuisine or of a noble glass of wine are, in the final analysis, savored through our sense of smell. In addition, before the spirit and beauty of a person can fascinate us, our nose must become infatuated. So, how do we register a smell? That our knowledge of the molecular background is still too scant is due to the complexity of the world of smell. More than 10000 odors can be distinguished, even in extremely low concentrations. The sense of smell is, thus, exceptionally specific and sensitive, and might best be compared in terms of complexity with the immune system. What happens in our nose, when we smell the odor of a rose? A basic question asked by Shakespeare. A flower or any odorous subject has to release molecules according to their vapor pressure into the air. During inhalation, they can reach our nasal cavity. As long as we breathe, we smell. The olfactory sense organ is a mucus membrane made up of an epithelium and a subepithelial lamina propria of connective tissue, blood vessels, and glands. In vertebrates, the olfactory epithelium consists of three mature cell types: bipolar primary sensory olfactory neurons, supporting cells, and two types of basal cells (adult stem cells), which generate olfactory-receptor neurons and supporting cells throughout our whole life.
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