1'-hydroxymyristicin

This is a minor metabolite of myristicin created in vivo after oral or topical use. ^[1] It also occurs naturally in nutmeg. This compound is not an alkaloid and is believed to have no psychedelic action in man.

The exact P450 enzyme responsible for creating this metabolite in the liver is currently unknown. The P450 enzymes CYP2C9, CYP2A6, CYP2D6, and CYP2E1 play a role in oxidizing the closely related allylbenzene safrole into 1'-hydroxysafrole.^[2]

Chemical Properties

Synonyms: Anthriscinol; 3-Methoxy-4,5-methylenedioxycinnamyl alcohol
PubChem Compound ID: 11389746
Molecular Weight: 180.20048 [g/mol]
Molecular Formula: C10H12O3
XLogP3-AA: 2.3
IUPAC Name: 3-methoxy-5-prop-2-enylbenzene-1,2-diol
InChI: InChI=1S/C10H12O3/c1-3-4-7-5-8(11)10(12)9(6-7)13-2/h3,5-6,11-12H,1,4H2,2H3
InChIKey: BHIIRUKUMCZDIB-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1O)O)CC=C

Bibliography

1. Yun CH, Lee HS, Lee HY, Yim SK, Kim KH, Kim E, Yea SS, Guengerich FP

Department of Genetic Engineering, Pai-Chai University, 439-6 Doma-dong, Seo-ku, Taejon 302-735, South Korea. Toxicology Letters [2003, 137(3):143-150]; Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin; DOI: 10.1016/S0378-4274(02)00397-1

2. 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