1'-Hydroxyestragole is a metabolite of the allylbenzene methyl chavicol (estragole) created by the action of several Cytochrome P450 enzymes.

The P450 enzymes primarily responsible for creating 1'-hydroxyestragole from methyl chavicol were identified as CYP1A2, CYP2A6, and CYP2E1.[1]

Metabolites Of 1'-Hydroxyestragole

1'-Hydroxyestragole glucuronide

This metabolite is created primarily by UGT2B7 and UGT1A9, and to a lesser extend by UGT2B15. These enzymes perform glucuronidation on 1'-hydroxyestragole creating 1'-hydroxyestragole glucuronide. This is a detoxification route.[2]


1'-Oxoestragole is created from 1'-hydroxyestragole by the action of estradiol-17beta-dehydrogenase (17beta-HSD2).[1] This metabolite is then capable of forming adducts with glutathione (GSH) leading to inactivation, or forming adducts with endogenous amines.[1] The latter action is believed to be responsible for the psychedelic effects methyl chavicol is capable of producing in humans under certain conditions. Adducts with glutathione (GSH) and certain endogenous amines form without the need for enzyme interaction. For more details see the article: 1'-Oxoestragole.

Chemical Properties

PubChem Compound ID: 40003
Molecular Weight: 164.20108 [g/mol]
Molecular Formula: C10H12O2
XLogP3-AA: 1.9
H-Bond Donor: 1
H-Bond Acceptor: 2
IUPAC Name: 1-(4-methoxyphenyl)prop-2-en-1-ol
InChI: InChI=1S/C10H12O2/c1-3-10(11)8-4-6-9(12-2)7-5-8/h3-7,10-11H,1H2,2H3
Canonical SMILES: COC1=CC=C(C=C1)C(C=C)O

1. Evaluation of human interindividual variation in bioactivation of estragole using physiologically based biokinetic modeling.
Punt A, Jeurissen SM, Boersma MG, Delatour T, Scholz G, Schilter B, van Bladeren PJ, Rietjens IM. PubMed: 19920071
2. Glucuronidation of 1'-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9.
Iyer LV, Ho MN, Shinn WM, Bradford WW, Tanga MJ, Nath SS, Green CE. PubMed: 12657745
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