This allylbenzene is found in betel leaf essential oil. It is reported to have stimulant effects. It is a major metabolite of safrole[1], and also a metabolite of eugenol[3], methyl eugenol[5] and chavibetol.

Xanthine Oxidase Inhibitor

Hydroxychavicol is an extremely potent xanthine oxidase inhibitor with an IC50 value 0.0167 µM.[2] Its more potent than allopurinol (IC50 0.0307 µM).[2]

Platelet Aggregation Inhibitor

Tests performed found hydroxychavicol was an inhibitor of platelet aggregation in vitro.[4]

COX-1/COX-2 inhibitor

Hydroxychavicol was found to be a potent inhibitor of COX-1 and COX-2 in vitro.[4]

Chemical Properties

Synonyms: 1,2-dihydroxyallylbenzene; 1,2-dihydroxy-4-allylbenzene; 2-hydroxychavicol
PubChem Compound ID: 70775
Molecular Weight: 150.1745 [g/mol]
Molecular Formula: C9H10O2
XLogP3: 0.8
IUPAC Name: 4-prop-2-enylbenzene-1,2-diol
InChI: InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2
Canonical SMILES: C=CCC1=CC(=C(C=C1)O)O

1. Safety evaluation of certain food additives; Prepared by the Sixty-ninth meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA); World Health Organization, Geneva, 2009; ISBN: 978-92-4-166060-0
2. Murata K, Nakao K, Hirata N, Namba K, Nomi T, Kitamura Y, Moriyama K, Shintani T, Iinuma M, Matsuda H;
Hydroxychavicol: a potent xanthine oxidase inhibitor obtained from the leaves of betel, Piper betle; School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka, 577-8502, Japan; J Nat Med. 2009 Jul;63(3):355-9. doi: 10.1007/s11418-009-0331-y. Epub 2009 Apr 22; PubMed PMID: 19387769; Brenda Enzymes Reference Data: 705237
3. Copper-mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation.
Sakano K, Inagaki Y, Oikawa S, Hiraku Y, Kawanishi S. PubMed PMID: 15576237
4. Hydroxychavicol, a novel betel leaf component, inhibits platelet aggregation by suppression of cyclooxygenase, thromboxane production and calcium mobilization.
Chang MC, Uang BJ, Tsai CY, Wu HL, Lin BR, Lee CS, Chen YJ, Chang CH, Tsai YL, Kao CJ, Jeng JH. PubMed PMID: 17641677
5. Metabolism of methyleugenol in liver microsomes and primary hepatocytes: pattern of metabolites, cytotoxicity, and DNA-adduct formation.
Cartus AT, Herrmann K, Weishaupt LW, Merz KH, Engst W, Glatt H, Schrenk D. PubMed PMID: 22610610
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License