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]

Biosynthesis of para anol and para chavicol

See also

References

  1. ^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. ISBN 0-8493-0486-5.
  2. ^ "Chavicol, 501-92-8".
  3. ^ Vassão, Daniel G.; Gang, David R.; Koeduka, Takao; Jackson, Brenda; Pichersky, Eran; Davin, Laurence B.; Lewis, Norman G. (2006). "Chavicol formation in sweet basil (Ocimum basilicum): Cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction". Org. Biomol. Chem. 4 (14): 2733–2744. doi:10.1039/b605407b. PMID 16826298.