Chavicol Explained

Chavicol (p-allylphenol) 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.[1]

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.[2]

See also

References

  1. Web site: Chavicol, 501-92-8.
  2. 10.1039/b605407b . Chavicol formation in sweet basil (Ocimum basilicum): Cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction . 2006 . Vassão . Daniel G. . Gang . David R. . Koeduka . Takao . Jackson . Brenda . Pichersky . Eran . Davin . Laurence B. . Lewis . Norman G. . Org. Biomol. Chem. . 4 . 14 . 2733–2744 . 16826298 .