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Aliphatic Compounds Used In Perfumery
- 1. Aliphatic Ingredients In Perfumery Chanchal Jadhav PGDPCM II Roll.no 1309
- 2. What are Aliphatic Compounds? • Organic compound containing carbon and hydrogen joined together in straight chains • Referred to as non-aromatic compounds • Aliphatic compounds can be saturated or unsaturated • Includes simple carbon chains, aldehydes, ketones, alkanes, carboxylic acids
- 3. Hydrocarbons • Saturated or unsaturated • Contribute to odour and taste to limited extent • Exception is (E,E)-1,3,5-Undecatriene and (3E, 5Z)- 1,3,5-Undecatriene
- 4. Alcohols • Free and esterified, saturated primary alcohols occur widely in nature e.g Fruits • Weak hence fragrance composition is limited • E.g PEA- Rosy, Bezyl alcohol, Ethyl Maltol, 3- octanol-mushroom like odour, tans-2-hexanol- green odour, geraniol, citronellol
- 5. Aldehydes • Aldehydes are most important components of perfumery • Lower Aldehydes impart fruity and roast character. E.g acetaldehyde, isobutyraldehyde, isovaleraldehyde, and 2-methyl-butyraldehyde • Unsaturated aliphatic aldehydes are important as fragrance and flavouring material. E.g 2-trans-6- cis-nonadienal- cucumber aroma and 2- trans,4- trans-Decadienal - fatty odor character like that in in chicken meat flavor compositions • E.g. Aldehydes C6, C8, C9, C10, C11, C12 • Acetals have odour characteristics similar to aldhydes but less pronounced
- 6. Ketones • Aliphatic ketones are of minor importance • Exception is odd numbered ketones like C7, C9 and C11 have a characteristic nutty note • E.g 3-Hydroxy-2-butanone- Plesant buttery odour - 2,3-Butanedione- a constituent of many fruit and food aromas and well-known as a constituent of butter - 3,4,5,6,6-Pentamethyl-3-hepten-2-one- woody floral note with amber and violet nuances - 2,4,4,7-Tetramethyl-6-octen-3-one- a fresh, green and citrus herbal top note
- 7. Acids and Esters • Aliphatic straight chain acids important in many foods and essential oils • Less important in fragrance substances • Important as starting materials in esters manufacture • Esters contribute to aromas of nearly all fruits and foods • E.g 2-Methyl-2-pentenoic acid- dry acid note, found in the odor of strawberries. - Allyl amylglycolate- strong fruity galbanum odor with pineapple modification -Aallyl caproate- typical pineapple odor - Ethyl 2-methylbutyrate- green-fruity odor reminiscent of apples - Isoamyl butyrate- strongly fruity odor that occurs, e.g., in banana. - Butyl butyrate- sweet-fruity odor - Ethyl propionate- a fruity odor reminiscent of rum
- 8. Thank you.
Editor's Notes
- 1. In organic chemistry, hydrocarbons are divided into two classes: aromatic compounds and aliphatic 2. An aliphatic compound is an organic compound containing carbon and hydrogen joined together in straight chains, branched chains, or non-aromatic rings. 3. Aliphatic compounds may contain single, double, or triple bonds. In other words, they may be saturated or unsaturated 4. Some aliphatics are cyclic molecules, but their rings are not as stable as those of aromatic compounds.
- Saturated and unsaturated aliphatic hydrocarbons with straight as well as branched chains occur abundantly in natural foodstuffs, But they contribute to the odor and taste only to a limited extent and have not therefore gained commercial importance 3. The only exceptions are the highly unsaturated hydrocarbons (E,Z)-1,3,5-undecatriene and (E,E)-1,3,5-Undecatriene 4. This group of materials is typically known as galbanum compounds. 5. (E,E)-1,3,5-Undecatriene, for example, which occurs in pineapple, has an oily, waxy, slightly fruity and peppery aroma. (See F-1.) It is also galbanumlike, green and musty, with an earthy odor and flavor. It may be applied as a green galbanum note in fragrances for toiletries, and in green vegetable flavor formulations 6. 3E,5Z)-1,3,5-Undecatriene occurs in apple, peach, pineapple, celery and parsley. (See F-2.) It has a power-ful, diffusive, green characteristic, galbanumlike odor and flavor. Application similar to that of (E,E)-1,3,5-Undecatriene
- Saturated primary alcohols occur widely in nature, e.g., in fruit. Since their odor is relatively weak, their use as components in fragrance compositions is limited. Unsaturated alcohols are most important (e.g., leaf alcohol with its intensely green odor) and may impart characteristic notes to compositions. Naturally occurring fatty alcohols used in the fragrance industry are produced principally by reduction of the methyl esters of the corresponding carboxylic acids, which are obtained by transesterification of natural fats and oils with methanol Alcohols are starting materials for aldehydes and esters Most commonly used are PEA, Benzyl alcohol, ethyl maltol, geraniol, citronellol, trans-2 hexanol, - octanol
- 1. Aliphatic aldehydes are among the most important components used in perfumery. 2. The lower aldehydes impart fruity and roast characters to flavor compositions. 3. Fatty aldehydes C8 –C13, however, are used, singly or in combination, in nearly all perfume types and also in aromas. 4. In addition to the straight-chain saturated aldehydes, a number of branched-chain and unsaturated aliphatic aldehydes are important as fragrance and flavoring materials. The double unsaturated 2-trans-6-cis-nonadienal [557-48-2], “violet leaf aldehyde” (the dominant component of cucumber aroma), is one of the most potent fragrance and flavoring substances; it is, therefore, only used in very small amounts. 2- trans,4-trans-Decadienal [25152-84-5] with its specifically fatty odor character is indispensable in chicken meat flavor compositions. 5. Acetals derived from aliphatic aldehydes have odor characteristics that resemble those of the aldehydes but are less pronounced. These acetals contribute to the aroma of alcoholic beverages, but can rarely be used in flavoring compositions because they are not sufficiently stable.
- Aliphatic monoketones are of minor importance as fragrance and aroma substances. 2-Alkanones (C3 –C15) have been found in the volatile fractions of many fruits and foodstuffs, but they do not contribute significantly to their aroma. An exception are the odd-numbered methyl ketones C7, C9, C11 which possess a characteristic nutty note; they are used, e.g., in cheese flavor compositions.
- Straight-chain, saturated aliphatic acids are found in many essential oils and foods. These acids contribute to aromas, but are not important as fragrance substances. However, straight-chain and some branched-chain aliphatic acids are of considerable importance as starting materials in the manufacture of esters, many of which are valuable fragrance and flavor materials. Aliphatic esters contribute to the aroma of nearly all fruits and many foods. Some are responsible for a particular fruit aroma, or for the smell of a particular flower; however, many of these esters possess a nonspecific fruity odor