Nerolidol

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trans-Nerolidol (top) and cis-Nerolidol (bottom)[1]
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Template:Longitem C15H26O
Molar mass 222.37 g/mol
Density 0.872 g/cm3
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Template:Longitem 1.4898

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Nerolidol, also known as peruviol and penetrol , is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers.[1] There are four isomers of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers.[2] Nerolidyl derivatives include nerolidyl diphosphate[3] and the fragrance nerolidyl acetate.[4]

Synthesis and occurrence

Nerolidol is produced commercially from geranylacetone, e.g., by the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1.[4]

File:GeranylacetoneToFarnesolviaNerolidol.svg
Conversion of geranylacetone to nerolidol, which can be isomerized to farnesol.

Significant sources of natural nerolidol is Cabreuva oil and the oil of Dalbergia parviflora.[4] It is also present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa, and lemon grass, and is a dominant scent compound in Brassavola nodosa.[5]

See also

References

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  1. a b Merck Index, 11th Edition, 6388.
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