Chavicol

Chavicol

Names
Preferred IUPAC name 4-(Prop-2-en-1-yl)phenol
Other names 4-Allylphenol; p-Allylphenol; para-Allylphenol
Identifiers
CAS Number	501-92-8  N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:50158  Y
ChEMBL	ChEMBL108862  Y
ChemSpider	21105856  Y
ECHA InfoCard	100.007.209
EC Number	207-929-2
KEGG	C16930
PubChem CID	68148
UNII	Q5ER4K6969  Y
CompTox Dashboard (EPA)	DTXSID60198210
InChI InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2 Y Key: RGIBXDHONMXTLI-UHFFFAOYSA-N Y InChI=1/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2 Key: RGIBXDHONMXTLI-UHFFFAOYAI
SMILES C=CCC1=CC=C(C=C1)O
Properties
Chemical formula	C9H10O
Molar mass	134.18 g/mol
Density	1.020 g/cm3
Melting point	16 °C (61 °F; 289 K)
Boiling point	238 °C (460 °F; 511 K) (123 °C at 16 mmHg)
Solubility in water	2.46 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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

• Estragole, the methyl ether
• Safrole, a methylenedioxy analog

References

1. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton, Florida: 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.