Perfumery

CioHi O. White leaflets, with a strong smell and sweet taste, m.p. 22 C, b.p. 235 C. The chief constituent of anise and fennel oils and other essential oils, from which it is manufactured. It can also be prepared from anisole (meihoxybenzene). It is widely used for flavouring pharmaceuticals and dentifrices, and in perfumery. 

CeHg02. A colourless liquid, b.p. 248 C. It occurs in aniseed and is used in synthetic perfumery under the name aubepine or artificial hawthorn. 

Prepared by the dehydration of benzamide. Hydrolysed by dilute acids and alkalis to benzoic acid. Good solvent. benzopheDone,C]3HioO,PhC(0)Ph. Colourless rhombic prisms, m.p. 49 C, b.p. 306°C. Characteristic smell. It is prepared by the action of benzoyl chloride upon benzene in the presence of aluminium chloride (Friedel-Crafts reaction) or by the oxidation of di-phenylmethane. It is much used in perfumery. Forms a kelyl with sodium. 

Trinitro-3-tert-butyltoluene, m.p. 97°C, yellow crystals. Used in perfumery and known as musk hour. 

CgHeOa. White crystals m.p. 37°C, b.p. 263°C. Occurs associated with vanillin. Obtained on oxidation of various natural products such as piperine. Used extensively in soap perfumery. 

Review Problem 2 This allyl bromide is an important intermediate in the synthesis of terpenes (including many flavouring and perfumery compounds), as the five carbon fi agment occurs widely in nature. How would you make it ... 

Revision Problem 1 Leaf alcohol (TM 392) is widespread in plants and has the characteristic smell of green leaves and grass. The cis isomer alone has tlfis smell and is used in perfumery. How would you make it ... 

Many essential oils are used for flavoting and perfumery, eg, neroH, geranium, and ylang (see Oils, essential). The whole fmit, cmshed fmit, and puree may be used directly in foods, ice cream, cakes, and confections. Fmit juices, concentrates, and essences are more commonly employed (see Fruit juices). 

Acetophenone can react with formaldehyde to yield light-resistant resins which are used as additives in nitrocellulose paints. It is also used as a photoinitiator, and in the pharmaceuticals, perfumery, and pesticide industries (344). It can be hydrogenated to 1-phenylethanol which is used for the production of aromatic ester fragrances (345). Technical-grade acetophenone is available at 2.29/kg perfume-grade acetophenone was 6.50/kg in October 1994. 

A commercially important outlet in the fragrance industry is the methyl dihydrojasmonate [24851-98-7] (26) which is made by Michael addition of a malonate to 2-pentyl-2-cyclopenten-l-one [91791 -21 -8] (52) and which is used in perfumery for blossom fragrances, particularly jasmine (see Perfumes). 

Of the 10 constituents which represent nearly half the oil of neroH, only linalool (10) can be said to contribute direcdy to the characteristic aroma of orange flower oil. In 1977, IFF chemists performed an in-depth analysis of this oil and identified three simple terpenic compounds, each present at less than 0.01%, a-terpenyl methyl ether [1457-68-0] (31), geranyl methyl ether [2565-82-4] (32), andhnalyl methyl ether [60763-44-2] (33) (11). The latter two compounds possess green floral-citms aromas and have been known to perfumery for some time a-terpenyl methyl ether (31) has been called the orange flower ether by IFF chemists owing to its characteristic odor. 

From a perfumery point of view, trace ingredients again play an important role in the typical aroma of citroneUa oil. In 1980, IFF chemists isolated and characterized two nonterpenic compounds, melonol (2,6-dimethyl-5-hepten-l-ol [4234-93-9]) and melonal (2,6-dimethyl-5-heptenal [106-72-9]) with interesting green-melon odors (10). Although neither of these had previously been reported in nature, melonal has been a product of commerce for a number of years. 

Sandalwood Oil, East Indian. The use of sandalwood oil for its perfumery value is ancient, probably extending back some 4000 years. Oil from the powdered wood and roots of the tree Santalum album L. is produced primarily in India, under government control. Good quaUty oil is a pale yellow to yellow viscous Hquid characterized by an extremely soft, sweet—woody, almost ariimal—balsarnic odor. The extreme tenacity of the aroma makes it an ideal blender—fixative for woody-Oriental—floral fragrance bases. It also finds extensive use for the codistillation of other essential oils, such as rose, especially in India. There the so-called attars are made with sandalwood oil distilled over the flowers or by distillation of these flowers into sandalwood oil. The principal constituents of sandalwood oil are shown in Table 11 (37) and Figure 2. 

Oakmoss. Extracts of oakmoss are extensively used in perfumery to furnisli parts of the notes of the fougnre or chypre type. The first step in the preparation of an oakmoss extract is treatment of the Hchen Evemiaprunastri (L.) Ach., collected from oak trees mainly in southern and central Europe, with a hydrocarbon solvent to obtain a concrete. The concrete is then further processed by solvent extraction or distillation to more usable products, of which absolutes are the most versatile for perfumery use. A definitive analysis of oakmoss volatiles was performed in 1975 (52). The principal constituents of a Yugoslav oakmoss are shown in Table 15 (53). A number of phenoHc compounds are responsible for the total odor impression. Of these, methyl P-orcinol carboxylate is the most characteristic of oakmoss. 

Clove bud oil is frequendy used iu perfumery for its natural sweet-spicy note but the greatest appHcation is iu the davor area iu a large variety of food products, including spice blends, seasoniugs, piddes, canned meats, baked goods, ready-made mixes, etc. As iu the case of cinnamon bark oil, its well-known antiseptic properties make it ideal for appHcation iu mouth washes, gargles, dentifrices, and pharmaceutical and dental preparations. Candy, particulady chewing gum, is also davored with clove bud oil iu combination with other essential oils. 

Lavender Oil Spike. Also known as spike oil, lavender oil spike is obtained by steam distillation of the flowering tops of l vandula latijolia Vik., which grows wild and is also cultivated throughout the Mediterranean region, with most production in Spain and France. There was a time when spike oil, particularly Spanish lavender oil [8016-78-2] found extensive use in soap perfumery however, with the introduction of the less expensive lavandin oil, a hybrid of tme lavender (L. angustifolid) and L. latijolia, utilization of spike oil in perfumery has been reduced appreciably. French spike oil, a more dehcate version, still finds considerable use in functional and industrial perfumery. A comparison of the volatiles of a commercial Spanish oil and a... 

Pimento Berry Oil. The pimento or allspice tree, Pimenta dioca L. (syn. P. officinalis, Liadl.), a native of the West Indies and Central America, yields two essential oils of commercial importance pimento berry oil and pimenta leaf oil. The leaf oil finds some use ia perfumery for its resemblance to clove leaf and cinnamon leaf oils as a result of its high content of eugenol. Pimento berry oil is an item of commerce with extensive appHcation by the flavor industry ia food products such as meat sauces, sausages, and pickles, and moderate use ia perfumery, where it is used primarily as a modifier ia the modem spicy types of men s fragrances. The oil is steam-distilled from dried, cmshed, fully grown but unripe fmits. It is a pale yellow Hquid with a warm-spicy, sweet odor with a fresh, clean topnote, a tenacious, sweet-balsamic-spicy body, and a tea-like undertone. A comparative analysis of the headspace volatiles of ripe pimento berries and a commercial oil has been performed and differences are shown ia Table 52 (95). 

Pine Oil. This oil is obtained by extraction and fractionation or by steam distillation of the wood of Pinuspalustris Mill, and other species. Most of the oil is produced ia the southeastern United States. The composition of the oil depends on the fractions chosen, but the chief constituents are terpene alcohols, mainly terpiaeol. Piae oil finds use as a germicide ia disiafectants and soaps as an ingredient ia iasecticides, deodorants, poHshes, sweepiag compounds, and catde sprays and as raw material for the manufacture of perfumery-grade terpiaeol [8000-41 -7], anethole [104-46-1], fenchone (137), and camphor (35). 

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