Chavicol

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Chavicol
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Molar mass 134.18 g/mol
Density 1.020 g/cm3
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Chavicol (p-allylphenol) is a natural phenylpropene, a type of organic compound.[1] Its chemical structure consists of a benzene ring substituted with a hydroxy group and a propenyl group. It is a colorless liquid found together with terpenes in betel oil.

Properties and reactions

Chavicol is miscible with alcohol, ether, and chloroform. Dimerization of chavicol gives the neo-lignan magnolol.

Uses

Chavicol is used as an odorant in perfumery and as a flavor. It is found in many essential oils, including anise and gardenia.[2]

Biosynthesis

Chavicol is formed in sweet basil (Ocimum Basilicum) by the phenylpropanoid pathway via p-coumaryl alcohol. The allylic alcohol in p-coumaryl alcohol is converted into a leaving group. This then leaves thus forming a cation, this cation can be regarded as a quinone methide which then is reduced by NADPH to form either anol or chavicol.[3]

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Biosynthesis of para anol and para chavicol

See also

References

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