Perfumes caryophyllene

Caryophyllene is the main hydrocarbon component of clove oil, from which it is produced as a by-product of eugenol extraction. The endocyclic double bond of caryophyllene is highly strained and reacts readily with a variety of reagents. Usually both double bonds become involved in a trans-annular reaction, followed by rearrangements to give mixtures of polycyclic products. Some of these mixtures find use as woody ingredients in perfumes. Caryophyllene and two typical reaction products from it are shown in Scheme 4.29. 

Caryophyllene (190) is the main constituent (> 50%) of Copaiba (balsam) oils, which are obtained by steam distillation of the exudate (balsam) from the trunk of several species of Copaifera L. (Fabaceae), a genus of trees growing in the Amazon basin [26]. Copaiba balsam oils and balsams are used mainly as fixatives in soap perfumes. 

Closely related to Java patchouli (P. heyneonus) known as false patchouli and sometimes used to produce an essential oil. The true oil is a viscous amber colour with a sweet earthy odour. Its main component is patchouli alcohol (up to 40%) with bulnesene (14-17%), seychellene (8.5-9.5%), caryophyllene (3-4%), 3-patchoulene (2.7-4%). There are a variety of attributed therapeutic properties. For the mind it is said to be a grounding oil helpful for those who feel depressed, detached and exhausted. Applied to the circulation it is considered stimulating, as a diuretic and for skin healing in conditions like acne and eczema. It is often used as a fixative in oriental perfumes, and a deodorizer as it masks unpleasant smells. Due to its very strong odour it is advisable to use in low proportions in a blend. Generally considered to be a safe oil as it is non-irritant and non-sensitizing. 

Clove leaf oil The crude oil is a dark brown to lilac brown, somewhat viscous liquid with a medical-phenolic, rough, burnt taste. For use in perfumes or flavors the crude oil is usually rectified to furnish a clear, yellow to light brown mobile liquid with a less burnt, sweet-spicy taste which is more dry-woody than the flower oil. It is produced from the leaves. Composition Like the flower oil, the leaf oil contains eugenol (ca. 85%) and caryophyllene (ca. 10% or more) as major components, but hardly any eugenyl acetate. 

Terpenes are components of various products e.g. tobacco smoke, wax pastes (furniture and floor polishes etc.), liquid waxes (floor polishes etc.), cleansers (detergents etc.), polishes, dyes and varnishes, synthetic resins, so-called natural building products, deodorants, perfumes, softeners, air fresheners, foods, beverages, pharmaceutical products (e.g. camomile oil, eucalyptus oil). In these products terpene compounds such as geraniol, myrcene (beta-myrcene), ocimene, menthol, alpha-pinene, beta-pinene, d-limonene, 3-carene, cineole, camphene or caryophyllene can be detected. 

Bicyclic sesquiterpenes caryophyllenes in essential oils, as perfume and fragrance products, chewing gum, synthesis of other perfumes typical odor (clove)... 

Beta-caryophyllene has been detected as one of the most abundant terpenes in P. caribaea by spectrometric methods [133]. This sesquiterpene has long been used in the perfume and cosmetics industry. Recently, using biotechnological approaches, phototrophic organisms have been genetically transformed to produce p-caryophyllene to be used by the biofuel industry [180]. 

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