Chavicol (''p''-allylphenol) is a natural

phenylpropene Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene. In plant biochemistry, the phenylprop ...

, a type of organic compound. Its chemical structure consists of a

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

ring substituted with a hydroxy group and a propenyl group. It is a colorless liquid found together with

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...

s in

betel The betel (''Piper betle'') is a vine of the family Piperaceae, which includes pepper and kava. The betel plant is native to Southeast Asia. It is an evergreen, dioecious perennial, with glossy heart-shaped leaves and white catkins. Betel plan ...

oil.

Properties and reactions

Chavicol is miscible with

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

, and

chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...

. Dimerization of chavicol gives the neo-lignan

magnolol Magnolol is an organic compound that is classified as lignan. It is a bioactive compound found in the bark of the Houpu magnolia (''Magnolia officinalis'') or in '' M. grandiflora''. The compound exists at the level of a few percent in the bark o ...

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 Basil (, ; ''Ocimum basilicum'' , also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also kno ...

(''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 reagrded as a quinone methide which then is reduced by

NADPH Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NAD ...

to form either

anol Anol, also known as ''para''-hydroxypropenylbenzene, is a simple phenol that was derived via demethylation from anethole, an estrogenic constituent of anise and fennel, by Sir Charles Dodds in 1937. It was reported to possess extremely potent ...

or chavicol.Daniel G. Vassao, David R. Gang, Takao Koeduka, Brenda Jackson, Eran Pichersky, Laurence B. Davina and Norman G. Lewis, Organic and Biomolecular Chemistry, 2006, 4, 2733-2744. DOI: 10.1039/b605407b Biosynthesis of chavicol

References

{{Phenylpropene Phenols Allyl compounds Perfume ingredients Phenylpropenes

Properties and reactions

Uses

Biosynthesis

See also

References