Ketones in perfumes

Aidehydes and Ketones in Perfumes 724 A Very Versatiie Vitamin, Pyridoxins (Vitamin Be) 744... 

In general, esters have sweet odors. For this reason, many are useful in perfumes or as flavorings. The boiling points of esters are similar to those of aldehydes and ketones of compcirable molar masses, which means that the boiling points cire lower than comparable alcohols. 

The ketone is used in perfume bases for soaps, eau de cologne, and detergent compositions. 

The indane ketone is a musk fragrance that is stable to light and in soap. It is used in perfumes and cosmetics for its fixative properties as well as its fragrance. FCT 1975 (13) p.693. 

Both aldehydes and ketones are industrially important classes of chemicals. Aldehydes are reduced to make the corresponding alcohols and are used in the manufacture of resins, dyes, plasticizers, and alcohols. Some aldehydes are ingredients in perfumes and flavors. Several ketones are excellent solvents and are widely used for that purpose to dissolve gums, resins, laquers, nitrocellulose, and other substances. 

Aldehydes and ketones are comparatively reactive materials and can be the cause of many stability problems in perfume compounds. Two of the most important types of reaction that are specific to these materials are the formation of acetals with alcohols, and the so-called... 

Essential oil from A. annua is another active research interest as it could be potentially used in perfume, cosmetics, and aromatherapy. Depending on its geographical origin, the oil yield in A. annua ranges from 0.02% to 0.49% on a fresh weight basis and from 0.04% to 1.9% on a dry weight basis. The major components in the oil were reported to be artemisia ketone (80), isoartemisia ketone (81), 1,8-cineole (82), and camphor (83) (Structure 5-5). GC/MS was employed to analyze the chemical composition in the essential oil more than 70 constituents have been identified. For more detailed information on the oil composition of essential oil from A. annua, the readers are referred to Refs. 65, 66 and 72-81. 

Also benzophenone [ 15] might act as an anthropogenic marker. It is mainly used along with substituted diphenyl ketones as UV-absorber in creams, as a fixative in perfumes and soap as well as an intermediate in pharmaceuticals and agricultural chemicals production. As well, only low concentrations were found in the Havel and Spree river sediments in the range of 0.5 to 3 ng/g, recommending an optimized analytical procedure. 

C oH,gO, Mr 154.25, liquid. Monocyclic monoter-pene ketones, the four optically active forms occur in nature. (-)-M. (ca. 35%) occurs in the essential oil of field mint (Mentha arvensis, Lamiaceae), (-i-)-M. in Micromelia biflora (Lamiaceae) ca. 56%, (-i-)-iso-M. in Micromelia abyssinica ca. 42%, and (-)-iso-M. in geranium oil (Pelargonium spp., Geraniaceae). p-M. is used in perfumes as a mixture with other fragrance substances. 

Many aldehydes and ketones have pleasant fragrances and, because of this, they have found use In perfumes. Originally, the Ingredients for perfumes came from natural sources such as essential oils (Seotlon 23.3), but with the development of synthetio organlo ohemistry In the nineteenth century, many Ingredients now used In perfumes result from the creativity of laboratory chemists. 

The following ketone, isolated from the roots of several members of the iris family, has an odor like that of violets and is used as a fragrance in perfumes. Describe the synthesis of this ketone from benzene. (See Examples 9.7,9.9)... 

Formyl-pinane can be isolated from the aldehyde mixture as pure compound in moderate yield by distillation with a column of 20 trays [70a]. In turn, the aldehyde was converted into the primary amine by reductive amination with ammonia. The chiral amine has been utilized, for example, for the optical resolution of racemic pantolactone. Alternatively, aldol condensation of the formed aldehydes with ketones and subsequent hydrogenation give alcohols that might have a broad scope of potential applications in perfumes, soaps, and shampoos [73]. 

Research suggests there are roles for pheromones in the lives of humans as well. For example, studies have shown that the phenomenon of menstrual synchronization among women who live or work with each other is likely caused by pheromones. Olfactory sensitivity to musk, which includes steroids such as androsterone, large cyclic ketones, and lactones (cyclic esters), also varies cyclically in women, differs between the sexes, and may influence our behavior. Some of these compounds are used in perfumes, including cive-tone, a natural product isolated from glands of the civet cat, and pentalide, a synthetic musk. 

The odor threshold values for methyl ketones are substantially higher than those for aldehydes (cf. Tables 3.32 and 3.47). Nevertheless, they act as aroma constituents, particularly in flavors of mold-ripened cheese (cf. 10.2.8.3). However, methyl ketones in coconut or palm oil or in milk fat provide an undesirable, unpleasant odor denoted as perfume rancidity . 

Baur went on to synthesize even better nitromusks, notably Musk Xylene, Musk Ketone and Musk Ambrette. These and similar molecules e.g. Musk Moskene and Musk Tibetine) became widely used in the perfume industry. The famous French perfumer Ernest Beaux reportedly used over 10% nitromusks, especially Musk Ketone, in Chanel No. 5 (1921), which reports indicate is still used in No. 5 today (see p333). Musk Ambrette s additional floral note was used to advantage... 

Other uses include use as a reaction and extraction solvent in pharmaceutical production as an intermediate for the preparation of catalysts, antioxidants (qv), and perfumes and as a feedstock in the production of methyl isopropenyl ketone, 2,3-butanedione, and methyl ethyl ketone peroxide. Concern has also arisen at the large volume of exported MEK which has been covertly diverted and used to process cocaine in Latin American countries... 

Methyl Isopropyl Ketone. Methyl isopropyl ketone [563-80-4] (3-methyl-2-butanone) is a colorless Hquid with a characteristic odor of lower ketones. It can be produced by hydrating isoprene over an acidic catalyst at 200—300°C (150,151) or by acid-catalyzed condensation of methyl ethyl ketone and formaldehyde to 2-methyl-l-buten-3-one, foUowed by hydrogenation to the product (152). Other patented preparations are known (155,156). Methyl isopropyl ketone is used as an intermediate in the production of pharmaceuticals and fragrances (see Perfumes), and as a solvent (157). It is domestically available from Eastman (Longview, Texas) (47). 

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