Chavicol

Chavicol is a natural phenylpropene, a type of organic compound. 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.

Biosynthesis

Chavicol is formed in sweet basil 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.