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Flavors and Fragrances 1 Flavors and Fragrances 1 Flavors and Fragrances Karl-Georg Fahlbusch, Corporate Research Division, DRAGOCO Gerberding & Co. Aktiengesellschaft, Holzminden, Federal Republic of Germany Franz-Josef Hammerschmidt, Corporate Research Division, DRAGOCO Gerberding & Co. Aktienge- sellschaft, Holzminden, Federal Republic of Germany Johannes Panten, Corporate Research Division, DRAGOCO Gerberding & Co. Aktiengesellschaft, Holzminden, Federal Republic of Germany Wilhelm Pickenhagen, Corporate Research Division, DRAGOCO Gerberding & Co. Aktiengesellschaft, Holzminden, Federal Republic of Germany Dietmar Schatkowski, Corporate Research Division, DRAGOCO Gerberding & Co. Aktiengesellschaft, Holzminden, Federal Republic of Germany based on the article of: Kurt Bauer, Haarmann & Reimer GmbH, Holzminden, Federal Republic of Germany Dorothea Garbe, Haarmann & Reimer GmbH, Holzminden, Federal Republic of Germany Horst Surburg, Haarmann & Reimer GmbH, Holzminden, Federal Republic of Germany (Chap. 3) 1. Introduction .............. 4 2.2.5.3. Citronellyl Esters ........... 27 1.1. The Chemical Senses ........ 4 2.2.6. Miscellaneous Compounds ..... 27 1.2. Definition ................ 4 2.3. Cyclic Terpenes ............ 28 1.3. History ................. 4 2.3.1. Hydrocarbons .............. 28 1.4. Odor Descriptors, Odor Thresh- 2.3.2. Alcohols and Ethers .......... 30 olds, Odor Value ........... 5 2.3.3. Aldehydes and Ketones ........ 34 1.4.1. Qualitative Measurements ...... 5 2.3.4. Esters ................... 40 1.4.2. Quantitative Measurements ..... 5 2.3.5. Miscellaneous Compounds ..... 42 1.4.2.1. Odor Threshold ............ 5 2.4. Other Cycloaliphatic Compounds 42 1.4.2.2. Odor Value ............... 5 2.4.1. Alcohols ................. 43 1.5. Regulations and Labeling Re- 2.4.2. Aldehydes ................ 44 quirements ............... 6 2.4.3. Ketones ................. 45 1.5.1. Flavors .................. 6 2.4.4. Esters ................... 48 1.5.2. Fragrances ................ 6 2.5. Aromatic Compounds ........ 50 2. Single Fragrance and Flavor Com- 2.5.1. Hydrocarbons .............. 50 pounds .................. 6 2.5.2. Alcohols and Ethers .......... 50 2.1. Aliphatic Compounds ........ 7 2.5.3. Aldehydes and Acetals ........ 53 2.1.1. Hydrocarbons .............. 7 2.5.4. Ketones ................. 56 2.1.2. Alcohols ................. 7 2.5.5. Esters of Araliphatic Alcohols and 2.1.3. Aldehydes and Acetals ........ 8 Aliphatic Acids ............. 59 2.1.4. Ketones ................. 11 2.5.6. Aromatic Acids ............ 60 2.1.5. Acids and Esters ............ 11 2.5.7. Esters Derived from Aromatic and 2.1.6. Miscellaneous Compounds ..... 14 Araliphatic Acids ........... 60 2.2. Acyclic Terpenes ........... 14 2.5.7.1. Benzoates ................ 60 2.2.1. Hydrocarbons .............. 14 2.5.7.2. Phenyl acetates ............. 61 2.2.2. Alcohols ................. 14 2.5.7.3. Cinnamates ............... 61 2.2.3. Aldehydes and Acetals ........ 21 2.5.8. Miscellaneous Compounds ..... 62 2.2.4. Ketones ................. 24 2.6. Phenols and Phenol Derivatives . 63 2.2.5. Acids and Esters ............ 25 2.6.1. Phenols, Phenyl Esters, and Phenyl 2.2.5.1. Geranyl and Neryl Esters ...... 25 Ethers ................... 63 2.2.5.2. Linalyl and Lavandulyl Esters ... 26 2.6.2. Phenol Alcohols and their Esters .. 67 c 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 10.1002/14356007.a11 141 2 Flavors and Fragrances 2.6.3. Phenol Aldehydes ........... 67 3.1. Introduction .............. 83 2.6.4. Phenol Ketones ............. 70 3.2. Isolation of Natural Fragrance 2.6.5. Phenol Carboxylates ......... 70 and Flavor Concentrates ...... 83 2.7. O- and O, S-Heterocycles ..... 72 3.2.1. Essential Oils .............. 84 2.7.1. Cyclic Ethers .............. 72 3.2.2. Extracts ................. 84 2.7.2. Lactones ................. 76 3.3. Survey of Natural Raw Materials 85 2.7.3. Glycidates ................ 81 4. Quality Control ............ 121 2.7.4. Miscellaneous Compounds ..... 81 5. Economic Aspects .......... 122 2.8. N- and N, S-Heterocycles ...... 81 6. Toxicology and Environmental 3. Natural Raw Materials in the Fla- Aspects ................. 122 vor and Fragrance Industry .... 83 7. References ............... 123 1. Introduction sense of sight has become predominant, odor in- fluences considerably the behavior, consciously 1.1. The Chemical Senses and subconsciously, it controls for example in- take of food and emotions and according to The sensations “taste” and “odor” are part of Proust helps in the “search for the past”. our five senses. Whereas seeing, hearing, and feeling react to a physical input (visible light waves, sound waves, and temperature and pres- 1.2. Definition sure, respectively) the two so-called chemical senses are stimulated by direct interactions with Flavor and fragrance compounds are molecules defined chemicals. The chemical senses are re- that stimulate the human chemical senses. The garded phylogenetically as the oldest senses, physiological importance of compounds that i.e., the earliest living species communicated by elicit a sensory reaction in other living beings emitting and receiving chemical signals in their apart from humans will not be treated in the con- aqueous environment. This communication sys- text of this paper. tem was refined when the first species left wa- In the following only compounds that stimu- ter to live on land and had to rely on molecules late the sense of smell for flavors and fragrances that were transported in the surrounding atmo- are discussed. These compounds, that are de- sphere. These molecules had to be volatile and tected in the upper end of the nose have to have were detected by the odor receptors which con- a certain volatility to be transported with the sequently developed to a much higher sophis- aspired air stream to the receptors. It is gen- tication than the taste receptors. The currently erally assumed that compounds with a molec- accepted doctrine is that only four basic taste ular mass > 300 are not volatile enough to ful- impressions (salty, sweet, sour, and bitter [1]) fill these conditions. Even if many compounds exist, whereas the types of odor impressions are are used both as flavor and fragrance ingredi- unlimited. Newer results, however, indicate that ents, some distinctions exist: in general, flavor the limitation to only four taste impressions is compounds consist of molecules that occur natu- too narrow and that more complex stimulations rally in edible materials whereas many fragrance to the sense of taste do exist [2]. compounds are not produced in nature (see Sec- According to E.L.Wick, the term flavor as tion 1.5). sensory impression results from the simultane- ous stimulation of the two chemical senses, odor and taste [3], so the description of volatile ma- 1.3. History terials will cover both flavor and fragrance ma- terials. As mentioned above, the sense of odor The history of odor is as old as the history of developed to a much higher degree than the sense mankind. Incense was already offered to the of taste and in some highly developed mammals God of the Sea in Ninive, in 5000 b.c. The (e.g., all canine species) became the most im- Gilgamesch Epos, which is considered to be portant sense of all. Even in humans, where the the oldest written document about the genesis Flavors and Fragrances 3 of mankind, mentions the use of cedarwood as compounds) for the synthesis of other not natu- source of odorants already in 3200 b.c. Sandal- rally occurring odorants. wood is described as part of the gifts that the Queen of Sheba gave to Salomon. Greeks and Romans used oil extracts of herbs and flowers 1.4. Odor Descriptors, Odor as therapeutic agents and for their sensory plea- Thresholds, Odor Value sures. During the middle ages, no real progress in preparing and using odorant materials was re- Odors can be measured and described qualita- ported, apart from the discovery of making con- tively and quantitatively, but contrary to the stim- centrated alcohol by the Arabs [4]. Real progress uli that elicit our other senses (i.e., sight, hear- in preparation of odorant compounds and mix- ing, touch, temperature) no physical analytical tures started nearly simultaneously with the be- method exist for odor measurement. ginning of organic chemistry which is marked by Wohler¨ ’s synthesis of urea [5]. Already in 1830, Wohler¨ and Liebig syn- 1.4.1. Qualitative Measurements thesized benzaldehyde, which was subsequently identified as the main aroma compound in Qualitative measurements are restricted to ver- bitter almonds by Robiquet and Boutron- bal descriptions of the odor impression. First Charlard in 1932. Worthy of mention is the approaches to classify odors by their descrip- synthesis of vanillin by Reimer and Thiemann tors were initiated by Harper, Bate Smith, and in 1876, which led to the foundation of the Ger- Land [9]. Their general conclusion is that the man flavor and fragrance industry. more complex the odor perception the more im- Analysis of food flavors proved to be cum- possible becomes an exact odor description. A bersome due to the very low natural abundance more detailed analysis into description of odors of these molecules and the analytical meth- and thus their qualitative measurement has been ods available at that time. By 1960, about 450 initiated by Kastner [10], who distinguishes molecules had been identified to occur in the three main descriptor categories, i.e., general de- volatile part of edible materials. scriptive terms, special descriptive terms, and The real breakthrough
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