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THE CHEMISTRY of FRAGRANCES RSC Paperbacks THE CHEMISTRY OF FRAGRANCES RSC Paperbacks RSC Paperbacks are a series of inexpensive texts suitable for teachers and students and give a clear, readable introduction to selected topics in chemistry. They should also appeal to the general chemist. For further information on available titles contact: Sales and Promotion Department, The Royal Society of Chemistry, Thomas Graham House, The Science Park, Cambridge CB4 OWF, UK Telephone: + 44 (0) 1223 420066 Fax: + 44 (0) 1223 423623 New Titles Available Food - The Chemistry of its Components (Third Edition) by T. P. Coultate Archaeological Chemistry by A. M. Pollard and C. Heron The Chemistry of Paper by J. C. Roberts Introduction to Glass Science and Technology by James E. Shelby Food Flavours: Biology and Chemistry by Carolyn Fisher and Thomas R. Scott Adhesion Science by J. Comyn The Chemistry of Polymers (Second Edition) by John W. Nicholson A Working Method Approach for Introductory Physical Chemistry Calculations by Brian Murphy, Clair Murphy and Brian J. Hathaway The Chemistry of Explosives by Jacqueline Akhavan Basic Principles of Inorganic Chemistry - Making the Connections by Brian Murphy, Clair Murphy and Brian J. Hathaway The Chemistry of Fragrances compiled by David Pybus and Charles Sell Existing titles may be obtained from the address below. Future titles may be obtained immediately on publication by placing a standing order for RSC Paperbacks. All orders should be addressed to: The Royal Society of Chemistry, Turpin Distribution Services Limited, Blackhorse Road, Letchworth, Herts SG6 IHN, UK Telephone: + 44 (0) 1462 672555 Fax: + 44 (0) 1462 280947 RSC Paperbacks THE CHEMISTRY OF FRAGRANCES Compiled by DAVID PYBUS and CHARLES SELL Quest International Ashford, Kent, UK ROYAL SOCIETY OF CHEMISTRY ISBN 0-85404-528-7 A catalogue record for this book is available from the British Library 0The Royal Society of Chemistry 1999 All rights reserved. Apart from any fair dealing for the purpose of research or private study, or criticism or review as permitted under the terms of the UK Copyright, Designs and Patents Act, 1988, this publication may not be reproduced, stored or transmitted, in any form or by any means, without the prior permission in writing of The Royal Society of Chemistry, or in the case of reprographic reproduction only in accordance with the terms of the licenses issued by the Copyright Licensing Agency in the UK, or in accordance with the terms of the licences issued by the appropriate Reproduction Rights Organization outside the UK. Enquiries concerning reproduction outside the terms stated here should be sent to The Royal Society of Chemistry at the address printed on this page. Published by The Royal Society of Chemistry, Thomas Graham House, Science Park, Milton Road, Cambridge CB4 OWF, UK For further information see our web site at www.rsc.org Typeset by Paston Prepress Ltd, Beccles, Suffolk, NR34 9QG Printed in Great Britain by Redwood Books Ltd, Trowbridge, Wiltshire Preface Modern perfumery is a blend of art, science and technology. Chemistry is the central science involved and the modern perfumery company houses specialists in all branches of chemistry, from physical chemists through analysts and synthetic organic chemists to biochemists. Indeed, the spectrum of skills ranges right across into biological fields, such as toxicology and sensory and behavioural sciences. All of these specialists work together with perfumers, and are essentially creative artists, accountants, marketeers and salespeople. No one person’s skill is sufficient to meet the needs of the business and all must pull together as a team. Our primary aim in this book is to show the use of chemistry in an exciting and rewarding business environment. However, we also felt that we should attempt to convey the interdisciplinary teamwork that is essential for success. To do this, we have invented a story that runs through the chapters and, hopefully, links them together in a way that shows how different specialists work together in a modern perfumery company. The story begins when a fragrance house receives a brief from a customer. Fragrance houses do not sell directly to the public but to customers who manufacture consumer goods. These customers are those companies whose names are well known to the general public. Some may sell only fine fragrances, others may specialize in house- hold cleaners. Yet others manufacture a broader spectrum, perhaps even the entire range from fine fragrances to industrial detergents. The customer in our story falls more into the last category and the brief asks for a perfume that can be used in a fine fragrance, but could also be ‘trickled down’ into a toilet soap, a shampoo and an antiperspirant. Such a request puts considerable constraints onto the creative perfumer, as described herein, and the combined efforts of perfumer and chemists are necessary to provide a suitable fragrance. vi Preface We hope that the story element adds to the enjoyment of the reader and gives a deeper understanding of the fascinating world of perfumery than would a simple factual account of the subject matter. David Pybus Charles Sell Contents Glossary xiv Chapter 1 A Home Full of Fragrance 1 David Pybus Chapter 2 The History of Aroma Chemistry and Perfume 3 David Pybus Early Use of Fragrance 4 The Age of Chivalry 9 The Age of Alchemy 9 The Age of Discovery 11 The Age of Revolution 15 The Age of Empire 17 Technique 18 Structured Perfumes, and Use of Synthetics 19 Industrialization and ‘Massification’ 19 The Age of Fashion 23 Chapter 3 Perfumery Materials of Natural Origin 24 Charles Sell Perfumes and Odours in Nature 24 Introduction 24 Biosynthesis 26 v11 ... Vlll Contents Extraction of Natural Perfume Ingredients 32 Expression 32 Distillation 33 Solvent Extraction 35 Adulteration of Natural Perfume Ingredients 39 From Natural to Synthetic 44 References 50 Chapter 4 Ingredients for the Modern Perfumery Industry 51 Charles Sell Economic Factors Affecting Perfume Ingredient Production 51 Perfume Ingredients Derived from Terpenes 52 Introduction 52 Five Key Terpenes 54 Hemiterpenes 63 Acyclic Monoterpenes 63 Cyclic Monoterpenes 67 Bicyclic Monoterpenes 76 Sesquiterpenes 78 Cedarwood 81 Sandalwood 83 Diterpenes 86 Ambergris 86 Ionones and Related Compounds 88 Musks 91 Nitromus ks 93 Polycyclic Musks 95 Macrocyclic Musks 98 Perfume Ingredients Derived from Benzene 10 1 Perfume Ingredients Derived from Toluene 105 Perfume Ingredients Derived from Phenol 108 Perfume Ingredients Derived from Naphthalene 114 Perfume Ingredients Derived from Aliphatic Materials 116 Perfume Ingredients Derived from Cyclopentanone 121 Perfume Ingredients Derived from Dicyclopentadiene 122 Conclusions 124 References 124 Con tents ix Chapter 5 The Structure of an International Fragrance Company 125 David Pybus Introduction 125 The Business-getting Chain 127 The Supply Chain 127 References 130 Chapter 6 The Fragrance Brief 131 David Pybus Brief for ‘Eve’, Prepared by Business Scents Ltd 133 Background 133 Product Range 134 General 134 Fragrance 134 Time-scale 135 Brief Recipients 135 Price 135 Production 135 Chapter 7 Perfume Creation: The Role of the Perfumer 137 Les Small Perfumery Degrees of Freedom 137 The Alcoholic Fragrance 139 Development of Other Products 141 Soap 141 Shampoo 142 Shower and Bath Gel 143 Antiperspirant 144 Conclusion 144 Reference 144 X Con tents Chapter 8 Measurement of Fragrance Perception 145 Anne Richardson Introduction 145 Market Research 146 Focus Groups 147 Quantitative Descriptive Analysis 147 Sensory Analysis 147 Threshold 148 Intensity 149 Quality 150 Statis t ical Techniques 151 Psychology of Perfume 153 The Business Scents Brief 154 Definition of the Appropriate Odour Area 154 Analysis of Ingredients to Convey the Appropriate Odour Characteristics 156 Creating Fragrances for the Future 156 Chapter 9 The Application of Fragrance 158 Judi Beerling The Role of an Applications Department 158 Product Formulations 159 Fine Fragrance 160 Vegetable Soap 161 Aerosol Antiperspirant 163 Shampoo 166 Shower and Bath Gel 168 Stability Testing 169 Humidity Testing 170 Light Testing 171 Assessment and Reporting of Results 171 Bibliography 173 Chapter 10 The Safety and Toxicology of Fragrances 174 Steve Meakins Introduction 174 Con tents xi Self-regulation 174 Safety Assessment 177 Skin Irritation 178 Skin Sensitization 179 Pho toeffects 182 Neuro toxicity 183 Reproductive Effects 185 Natural Ingredients 186 Conclusions 186 References 186 Chapter 11 Volatility and Substantivity 188 Keith D. Perring Perfume Creation and Physical Chemistry 188 Perfume Ingredient Volatility 189 Perfume Polarity 193 Substantivity and Retention 197 Conclusions 200 References 20 1 Chapter 12 Natural Product Analysis in the Fragrance Industry 202 Robin Clery Introduction 202 Natural Product Analysis 202 The Traditional Approach 203 The Headspace Approach 204 Analytical Techniques Used in the Fragrance Industry 206 Extraction 206 Gas-Liquid Chromatography 207 Preparative Liquid Chromatography 21 1 Positive Identification 212 Headspace Collection 21 3 References 215 xii Con tents Chapter 13 Chemoreception 216 Charles Sell Background 216 Theories 217 Biological Facts 220 Misconceptions 223 Conclusions 225 References 226 Further Reading 226 Chapter 14 Electronic Odour Sensing 227 Jenny Oliver Introduction 227 Electronic Aroma-sensing Systems 228 Possible Uses of an Electronic Odour-sensing System 23 1 Conclusion 232 References 232 Chapter I5 The Search for New Fragrance Ingredients 233 Karen Rossiter Introduction
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