Hui, Y.H. (ed.)
Handbook of Fruit and Vegetable Flavors
2010
Print ISBN: 978-0-470-22721-3
Adobe PDF ISBN: 978-0-470-62282-7
Adobe PDF ISBN: 978-0-470-62283-4
ePub ISBN: 978-1-118-03185-8
MobiPocket ISBN: 978-1-118-12487-1
Sawamura, M. (ed.)
Citrus Essential Oils
Flavor and Fragrance
2010
Print ISBN: 978-0-470-37218-0
Adobe PDF ISBN: 978-0-470-61315-3
Adobe PDF ISBN: 978-0-470-61316-0
ePub ISBN: 978-1-118-07438-1
MobiPocket ISBN: 978-1-118-12635-6
Tao, J., Kazlauskas, R.J. (eds.)
Biocatalysis for Green Chemistry and Chemical Process Development
2011
Print ISBN: 978-0-470-43778-0
Adobe PDF ISBN: 978-1-118-02828-5
ePub ISBN: 978-1-118-02829-2
Adobe PDF ISBN: 978-1-118-02830-8
MobiPocket ISBN: 978-1-118-35343-1
Dayan, N., Kromidas, L. (eds.)
Formulating, Packaging, and Marketing of Natural Cosmetic Products
2011
Print ISBN: 978-0-470-48408-1
Adobe PDF ISBN: 978-1-118-05678-3
ePub ISBN: 978-1-118-05679-0
Adobe PDF ISBN: 978-1-118-05680-6
MobiPocket ISBN: 978-1-118-35347-9
Sell, C.S.
Chemistry and the Sense of Smell
2014
Print ISBN: 978-0-470-55130-1
ePub ISBN: 978-1-118-52296-7
ISBN: 978-1-118-52298-1
Adobe PDF ISBN: 978-1-118-52314-8
Herrmann, A. (ed.)
The Chemistry and Biology of Volatiles
2010
Print ISBN: 978-0-470-77778-7
ISBN: 978-0-470-66953-2
Adobe PDF ISBN: 978-0-470-66955-6
ePub ISBN: 978-1-119-95698-3
MobiPocket ISBN: 978-1-119-95699-0
P.M., V., Iturriaga, L.B., Ribotta, P.
Advances in Food Science and Nutrition, Volume 2
2013
Print ISBN: 978-1-118-13709-3
Adobe PDF ISBN: 978-1-118-86553-8
Adobe PDF ISBN: 978-1-118-86560-6
ePub ISBN: 978-1-118-86563-7
Kirk-Othmer (ed.)
Kirk-Othmer Chemical Technology of Cosmetics
2013
Print ISBN: 978-1-118-40692-2
ePub ISBN: 978-1-118-51890-8
MobiPocket ISBN: 978-1-118-51896-0
Adobe PDF ISBN: 978-1-118-51898-4
Goodner, K.K. (ed.)
Practical Analysis of Flavor and FragranceMaterials
2011
Print ISBN: 978-1-405-13916-8
ePub ISBN: 978-1-119-97521-2
MobiPocket ISBN: 978-1-119-97522-9
ISBN: 978-1-444-34313-7
Adobe PDF ISBN: 978-1-444-34314-4
Food Flavour Technology 2e
2010
Print ISBN: 978-1-405-18543-1
ISBN: 978-1-444-31777-0
Adobe PDF ISBN: 978-1-444-31778-7
Smith, J., Hong-Shum, L. (eds.)
Food Additives Databook 2e
2 Edition
2011
Print ISBN: 978-1-405-19543-0
MobiPocket ISBN: 978-1-444-35479-9
Adobe PDF ISBN: 978-1-444-39772-7
ePub ISBN: 978-1-444-39773-4
ISBN: 978-1-444-39774-1
Bart, H., Pilz, S. (eds.)
Industrial Scale Natural Products Extraction
2011
Print ISBN: 978-3-527-32504-7
ISBN: 978-3-527-63512-2
ePub ISBN: 978-3-527-63513-9
Adobe PDF ISBN: 978-3-527-63514-6
MobiPocket ISBN: 978-3-527-63515-3
De Rovira, D.A.
Dictionary of Flavors, Second Edition
2 Edition
2008
Print ISBN: 978-0-813-82135-1
Adobe PDF ISBN: 978-0-470-38484-8
ISBN: 978-0-470-38506-7
6 completely revised and updated Edition
Authors
Dr. Horst Surburg
Meiernberg 9
37603 Holzminden
Germany
Dr. Johannes Panten
Symrise AG
RD Synthesis
Bldg. D 209
Mühlenfeldstr. 1
37603 Holzminden
Germany
All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, 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.
Library of Congress Card No.: applied for
British Library Cataloguing-in-Publication Data
A catalogue record for this book is available from the British Library.
Bibliographic information published by the Deutsche Nationalbibliothek
The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at <http://dnb.d-nb.de>.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA,
Boschstr. 12, 69469 Weinheim, Germany
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.
Print ISBN: 978-3-527-33160-4
ePDF ISBN: 978-3-527-69317-7
ePub ISBN: 978-3-527-69318-4
Mobi ISBN: 978-3-527-69316-0
oBook ISBN: 978-3-527-69315-3
Cover Design Adam Design
Since its first publication 31 years ago, “Common Fragrance and Flavor Materials” became an indispensable tool for all people in the fragrance and flavor chemistry world. Also, in all parts of our life, things are moving ahead in this exciting field and, therefore, make it necessary to publish a new edition.
Traditionally, the concept of this book was not changed; however, several updates were added.
These are, among others, a revision of the sensorial descriptions in Chapter 1. In Chapter 2, several new and commonly available compounds were added. In addition, new production processes were introduced. Citations of Food Chem Tox as well as the commercial names were revised. Chapter 3 was amended by new raw materials and the citation and publication list was updated. As the registration and legislation situation especially in Europe has changed, it became necessary to revise Chapter 5. New references on safety data sheets and an updated citation list of patents complete this revision.
It is, however, not possible to review and to cite every new development in the field of fragrance and flavor raw materials. We decided, for example, not to include the development of precursor systems as this will go beyond the scope of this book.
The responsible authors for the sixth edition are still Horst Surburg and Johannes Panten, both of whom were or are still working in the synthesis department of the corporate research division of Symrise AG in Holzminden.
Both authors are indebted to many colleagues for their support and to the management of Symrise AG for the opportunity to prepare the sixth edition of this book.
Holzminden, July 2015
Horst Surburg
Johannes Panten
In the last two decades, “Common Fragrance and Flavor Materials” has developed to become probably the most cited standard work in the field of fragrance and flavor chemistry, and continual demand has now made it necessary to publish a new edition.
With regard to the contents, an update was required for several reasons, as some remarkable changes in the compositions of perfume oils – increasing use of macrocyclic musk materials has been observed, for example – have occurred since the publication of the 4th edition. Consequently, chapter 2 has had to be extended with some new monographs.
Some other trend-setting materials have also had to be included, whilst other materials that had lost their importance have had to be eliminated.
The changes in the landscape of fragrance and flavor materials producers also required corresponding adjustments.
The class of cooling agents – materials that create a cold sensation on skin or mucosa – has been admitted for the first time. Although known in principle for a long time, cooling agents have recently acquired increasing importance.
Chapter 3 has been partly revised and updated with regard to recent literature. Since it is impossible to cite the whole literature comprehensively, it was decided to refer to current review literature where possible. Otherwise, some of the very recent original references have been cited.
In general, the successful conception of this book, established about 20 years ago by Kurt Bauer and Dorothea Garbe, has been maintained. For a long time both of these authors worked in the research department of the flavor and fragrance company Haarmann & Reimer in Holzminden, Germany, Kurt Bauer as director of research and Dorothea Garbe as head of the department for scientific literature and documentation. Both retired some years ago and are therefore no longer engaged in the preparation of the 5th edition.
The responsible authors are now Horst Surburg and Johannes Panten, both of whom work in the synthesis department of the corporate research division of “Symrise”, the company formed by the merger of the flavor and fragrance houses “Dragoco” and “Haarmann & Reimer” in Holzminden.
Both authors are indebted to many colleagues for their support and to the management of Symrise for the opportunity to prepare the 5th edition of this book.
Holzminden, December 2005
Horst Surburg
Johannes Panten
The constant interest in “Common Fragrance and Flavor Materials” has encouraged us to proceed with the publication of a new edition within a relatively short period of time. The proven concept of the book has remained unchanged because of positive feedback from readers.
After a critical examination of the text, some material that has lost significance has been removed. A certain amount of new material, mainly components that have influenced modern fragrance trends over the past few years, have been added. The literature references in the chapter on “Natural Raw Materials” have been updated and the newest international standards for the characterization of materials have been included.
The authors would like to point out particularly that the present book can only provide a selection of the many commercially available fragrance and flavor materials. Also not included are compounds with exclusive uses that are not commonly/ generally available (“captives”) as well as substances that are too new to be judged as to whether they will find a successful place in the market. Analytical data on natural raw materials that can be obtained by means of new analytical techniques are not explicitly mentioned if the analytical techniques have not yet reached international standardization. However, reference is made to this in the corresponding literature and in the chapter on “Quality Control.”
We thank our critics for numerous suggestions and we especially thank our colleagues, who prompted our work on the new edition through their kind support.
Holzminden, June 2001
K. Bauer
D. Garbe
H. Surburg
Twelve years after its first publication comes the third edition of “Common Fragrance and Flavor Materials”. The content has been updated in many respects while retaining the proven concept.
In the case of the single-component fragrance and flavor materials, those compounds have been included which have become established on the market, as well as those which have attracted considerable interest on account of their outstanding organoleptic properties and have contributed to the composition of new fragrance types. The production processes for all fragrance and flavor materials described in the book have been critically reviewed. New processes have been taken into account, and those that are clearly outdated have been eliminated. A few compounds that have declined in importance or whose use is now restricted for toxicological reasons have been removed from the text, as have several essential oils. The latest publications and standards concerning essential oils and natural raw materials have been included in the new edition, making it an up-to-date reference work. For the first time references are cited for all essential oils, giving newcomers to the field a quick overview of the original literature. The chapters on quality control and product safety have been expanded and brought up to date.
The authors wish to thank all the colleagues whose specialist advice assisted us in revising the book.
Holzminden, February 1997
K. Bauer
D. Garbe
H. Surburg
Within three years of publication the first edition of “Common Fragrance and Flavor Materials” was out of print and is now followed by this second edition. As in the case of the first edition this book is based mainly on a chapter on “Flavors and Fragrances” which has since been published in English in Ullmann's Encyclopedia of Industrial Chemistry.
We would like to thank our readers for their suggestions for improvement and further development of the contents which were contained in several book reviews. We have not followed up all the suggestions for the simple reason that we did not wish to change the character of the book, which is expressly aimed at a general audience interested in commonly used fragrance and flavor materials, and not at experts in the field.
The chapter on “Single Fragrance and Flavor Compounds” has been updated to include new developments, production methods have been brought up-to-date and CAS registry numbers have been added to all single compounds described. The former chapters “Essential Oils” and “Animal Secretions” have been grouped together under the heading “Natural Raw Materials in the Flavor and Fragrance Industry” and thoroughly revised to include new literature references.
Holzminden, February 1990
K. Bauer
D. Garbe
H. Surburg
Fragrance and flavor materials are used in a wide variety of products, such as soaps, cosmetics, toiletries, detergents, alcoholic and non-alcoholic beverages, ice cream, confectioneries, baked goods, convenience foods, tobacco products, and pharmaceutical preparations. This book presents a survey of those natural and synthetic fragrance and flavor materials which are produced commercially on a relatively large scale, or which are important because of their specific organoleptic properties. It provides information concerning their properties, methods employed in their manufacture, and areas of application. Therefore, the book should be of interest to anyone involved or interested in fragrance and flavor, e.g., perfumers, flavorists, individuals active in perfume and flavor application, food technologists, chemists, and even laymen.
The book is, essentially, a translation of the chapter on fragrance and flavor materials in Ullmanns Encyklopädie der technischen Chemie, Volume 20, 4th Edition, Verlag Chemie GmbH, Weinheim (Federal Republic of Germany), 1981. The original (German) text has been supplemented by inclusion of recent developments and of relevant information from other sections of the Encyclopedia. The present English version will make the information available to a wider circle of interested readers.
The condensed style of presentation of “Ullmann's” has been maintained. A more detailed treatment of various items and aspects was considered but was believed to be outside the scope of this book. Additional information, however, can be obtained from the literature cited.
To improve its usefulness, the book contains
Starting materials and intermediates are not covered by these indexes. The authors wish to express their gratitude to:
The authors are most grateful to Dr. J. J. Kettenes-van den Bosch and Dr. D. K. Kettenes for translating the original German text into English and for their suggestions and help in shaping the present book. Drs. Kettenes thank Mr. W. S. Alexander, Hockessin, Delaware (USA), for critically reviewing the English.
Holzminden, June 1984
K. Bauer
D. Garbe
Since early antiquity, spices and resins from animal and plant sources have been used extensively for perfumery and flavor purposes and to a lesser extent for their observed or presumed preservative properties. Fragrance and flavor materials vary from highly complex mixtures to single chemicals. Their history began when people discovered that component characteristic of the aroma of natural products could be enriched by simple methods. Recipes for extraction with olive oil and for distillation have survived from pre-Christian times to this day.
Although distillation techniques were improved, particularly in the ninth century A.D. by the Arabs, the production and application of these concoctions remained essentially unchanged for centuries. Systematic development began in the thirteenth century, when pharmacies started to prepare the so-called remedy oils and later recorded the properties and physiological effects of these oils in pharmacopoeias. Many essential oils currently used by perfumers and flavorists were originally prepared by distillation in pharmacies in the sixteenth and seventeenth centuries.
Another important step in the history of natural fragrance materials occurred in the first half of the nineteenth century, when the production of essential oils was industrialized due to the increased demand for these oils as perfume and flavor ingredients. Around 1850, single organic compounds were also used for the same purposes. This development resulted from the isolation of cinnamaldehyde from cinnamon oil by Dumas and Pèligot in 1834, and the isolation of benzaldehyde from bitter almond oil by Liebig and Wöhler in 1837. The first synthetic “aroma oils” were introduced between 1845 and 1850. These consisted of lower molecular mass fatty acid esters of several alcohols and were synthesized by the chemical industry for their fruity odor. Methyl salicylate was introduced in 1859 as “artificial wintergreen oil” and benzaldehyde in 1870 as “artificial bitter almond oil.” With the industrial synthesis of vanillin (1874) and coumarin (1878) by Haarmann & Reimer (Holzminden, Germany), a new branch of the chemical industry was founded.
The number of synthetically produced fragrance and flavor chemicals has since expanded continually as a result of the systematic investigation of essential oils and fragrance complexes for odoriferous compounds. Initially, only major components were isolated from natural products; their structure was then elucidated and processes were developed for their isolation or synthesis. With the development of modern analytical techniques, however, it became possible to isolate and identify characteristic fragrance and flavor substances that occur in the natural products in only trace amounts. The isolation and structure elucidation of these components require the use of sophisticated chromatographic and spectroscopic techniques. Interesting products can then be synthesized.
Fragrance and flavor substances are comparatively strong-smelling organic compounds with characteristic, usually pleasant odors. They are, therefore, used in perfumes and perfumed products, as well as for the flavoring of foods and beverages. Whether a particular product is called a fragrance or a flavor substance depends on whether it is used as a perfume or a flavor. Fragrances and flavors are, similar to taste substances, chemical messengers, their receptors being the olfactory cells in the nose [1, 2].
Chemical signals are indispensable for the survival of many organisms which use chemoreceptors to find their way, to hunt for and inspect food, to detect enemies and harmful objects, and to find members of the opposite sex (pheromones). These functions are no longer vitally important for humans. The importance of flavor and fragrance substances in humans has evolved to become quantitatively and qualitatively different from that in other mammals; this is because humans depend to a greater extent on acoustic and optical signals for orientation. However, humans have retained the ability to detect odors, and human behavior can undoubtedly be affected by fragrances and aromas.
Sensory information obtained from the interaction of fragrance and flavor molecules with olfactory and taste receptors is processed in defined cerebral areas, resulting in perception. During the past 15 years, much research was done concerning sensory perception, and the results have been published in, for example, [2–23].
Although food acceptance in humans is determined mainly by appearance and texture, flavor is nevertheless also important. For example, spices are added to food not for their nutritional value but for their taste and flavor. Furthermore, aromas that develop during frying and baking enhance the enjoyment of food. Unlike flavoring substances, fragrances are not vitally important for humans. The use of fragrances in perfumery is primarily directed toward invoking pleasurable sensations by shifting the organism's emotional level. Whereas “naturalness” is preferred in aromas (generally mixtures of many compounds), the talent and imagination of the perfumer are essential for the creation of a perfume.
Natural compounds are obtained directly from natural sources by physical or biotechnological (enzymatic, microbial) procedures. As a result of the rapid development and expansion of biotechnology in the past two decades, far more than 100 natural flavoring substances are available from biocatalytic processes today [24–26]. Nature-identical compounds are produced synthetically but are chemically identical to their natural counterparts. Artificial flavor substances are compounds that have not yet been identified in plant or animal products for human consumption [27]. Alcohols, aldehydes, ketones, esters, and lactones are classes of compounds that are represented most frequently in natural and artificial fragrances.
Nature-identical aroma substances are, with very few exceptions, the only synthetic compounds used in flavors besides natural products. The primary functions of the olfactory and taste receptors, as well as their evolutionary development, may explain why artificial flavor substances are far less important. A considerable proportion of compounds used in fragrances are those identified as components of natural products, for example, constituents of essential oils or resins. The fragrance characteristics of artificial compounds nearly always mimic those of natural products.
Similarity between odors arises because dissimilar substances or mixtures of compounds may interact with receptors to create similar sensory impressions in the sensory centers of the brain. The group of musk fragrances (comprising macrocyclic ketones and esters as well as aromatic nitro compounds and polycyclic aromatics), for example, are compounds with similar odors but totally different structures [28, 29]. Small changes in the structure (e.g., the introduction of one or more double bonds in aliphatic alcohols or aldehydes) may, however, alter a sensory impression or intensify an odor by several orders of magnitude. Increasing knowledge of the structure and functioning of olfactory receptors provides a better scientific basis for the correlation of odor and structure in fragrance and flavor substances and facilitates the more accurate prediction of the odors of still unknown compounds [30–52].
Fragrances must be volatile to be perceived. Therefore, in addition to the nature of the functional groups and the molecular structure of a compound, the molecular mass is also an important factor. Molecular masses of about 200 occur relatively frequently; masses over 300 are an exception.
Since fragrance materials differ in volatility, the odor of a perfume composition changes during evaporation and is divided into the top note, the middle note or body, and the end note or dry-out, which consists mainly of less volatile compounds. Odor perception also depends largely on odor intensity. Therefore, the typical note is not determined only by the most volatile compounds.
In some cases, substances (fixatives) are added to perfumes to prevent the more volatile components from evaporating too rapidly [53].
Due to the specificity of olfactory receptors, some compounds can be perceived in extremely low concentrations and significant differences in threshold concentrations are observed. The threshold concentration is defined as the lowest concentration at which a chemical compound can be distinguished with certainty from a blank under standard conditions.
For the compounds described in Chapter 2, threshold concentrations vary by a factor of 106–107. This explains why some fragrance and flavor materials are manufactured in quantities of a few kilograms per year, others in quantities of several thousands of tons.
The relative contribution of a particular compound (its odor or flavor value) to the odor impression of a composition can be expressed as the ratio between the actual concentration of the compound and its threshold concentration [54, 55].
The sensory properties of single aroma chemicals are extremely difficult to describe unequivocally. Complex mixtures are often impossible to describe unless one of the components is so characteristic that it largely determines the odor or flavor of the composition. Although a classification is always subjective, sensory properties can be described by adjectives such as flowery, fruity, woody, hay-like, which relate the fragrances or flavors to natural or other known products with similar sensory impressions [56]. However, such terms are not strictly defined and run into each other. In most cases, sensory properties of one and the same material can only be described by using more than one term.
In accordance with the evolution of its fragrance properties, a perfume composition can formally be divided into three categories: top note, heart note (body; bouquet), and base note (fond).
In classic perfumes of feminine and masculine types, the heart note consists of fragrance materials with a floral character. It is enveloped by materials that are perceived immediately (top notes) and materials that are perceived mainly in the dry-out and impart tenacity to the composition (base notes). In a striking illustration of a “fragrance circle,” a circular central body is ringed by segments of top notes in the upper part and by base notes in the lower part [57]. The segments contain the most important fragrance categories that determine the character of a perfume.
Typical top notes are as follows:
| Citrus | Fresh, stimulating odor of citrus fruits such as lemon, lime, orange, bergamot |
| Aldehydic | Odor note of the long-chained fatty aldehydes: fatty-sweaty, ironed laundry, metallic, fresh seawater, ozone-like, marine fragrances |
| Fruity | Light fruity notes: typical notes of aliphatic esters: found, for example, in odors of apples, pears, melons |
| Dark (heavy, sweet) fruity notes: found, for example, in odors of strawberries, raspberries, lactone odor of peaches and coconuts | |
| Green | Typical odor of green vegetation: green leaves and freshly cut grass |
| Herbaceous/Herbal | Odor of green herbs and spices, for example, sage, mint, eucalyptus; camphoraceous such as rosemary; coniferous such as fir needles; earthy agrestic |
Examples of floral notes (heart notes; body) are as follows:
| Floral light | Rose |
| Floral green, clean | Lily of the Valley (muguet) |
| Floral fresh, herbal | Geranium, lavender |
| Floral fruity | For example, damascones |
| Floral heavy | Narcotic flower fragrances such as jasmine, tuberose |
| Floral woody (powdery) | For example, methylionones |
Typical base notes are as follows:
| Aromatic | Sweet aromatic to aromatic spicy odors, for example, of honey, almond, aniseed, woodruff, nutmeg, clove. This segment also contains the so-called gourmand notes having pronounced culinary properties, for example, vanilla, tonka, lovage |
| Balsamic | Heavy sweet odors, such as chocolate and vanilla, cinnamon with resinous elements |
| Moss | Dry, algae-like, tar-like, phenolic, oak moss |
| Leather, animalic | Odor of cresol, isobutyl quinoline, and so on; fecal such as indole |
| Musk | Warm soft odor reminding of freshly washed and ironed laundry, often with skin-like and animalic-erogenous facets |
| Amber | Warm, slightly earthy-camphoraceous woody note, reminding natural ambergris, represented typically by amber oxide |
| Wood | Clear cool radiant odor found in natural materials such as cedarwood (pencil note), patchouli, sandalwood, and vetiver |
In addition to these generic properties, a number of specific terms are used to characterize fragrance material more in detail, for example, fatty, waxy, burnt, phenolic, fishy, sulfurous, musty, medicinal, [57].
Sensory properties of flavoring substances can simply be illustrated when arranged in segments of a circle, “flavor wheel” [58], containing the following descriptors:
Green, grassy; herbaceous; spicy; fruity, ester-like; tropical; blackcurrant; vegetable; nutty; caramel; smoky; roast, burnt; beefy; pork, lamb, chicken; savory, bouillon; fatty; rancid, cheesy; mushroom, earthy; truffle; garlic; onion.