Tests performed in rats found the metabolite 3'-hydroxyisosafrole occurred in urine after oral ingestion of safrole as a minor metabolite, but this was not in urine of human test subjects.[1]

In rats and mice, 3'-Hydroxyisosafrole was found to lead to the creation of alkaloid metabolites. The metabolism of 3'-hydroxyisosafrole in the rat and mouse differed from 1'-hydroxysafrole. 3'-Hydroxyisosafrole rapidly underwent side-chain oxidation giving 3,4-methylenedioxycinnamic acid and 3,4-methylenedioxybenzoic acid. In the first 4 hours, the major urinary alkaloid metabolites 3,4-methylenedioxybenzoyl glycine and 3,4-methylenedioxycinnamoyl glycine, adducts of glycine, together accounted for 39% and 63% of the dose administered to rats and mice, respectively. The glucuronide of 3'-hydroxyisosafrole was not detected in the urine. Urinary excretion of the glucuronide of 1'-hydroxysafrole at 2 hours accounted for about 40% of a dose of 1'-hydroxysafrole.[2]

Chemical Properties

Synonyms: 3,4-Methylenedioxycinnamyl alcohol;
IUPAC Name: (E)-3-(1,3-benzodioxol-5-yl)prop-2-en-1-ol
PubChem CID: 5869753
Molecular Formula: C10H10O3
Molecular Weight: 178.187 g/mol
XLogP3: 1.9
Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=CCO
Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C/CO
CAS # 17581-86-1

1. Toxicology. 1977 Feb;7(1):69-83.
Absorption, metabolism and excretion of safrole in the rat and man. Benedetti MS, Malnoƫ A, Broillet AL; PubMed PMID: 14422
2. The metabolic sulfonation and side-chain oxidation of 3'-hydroxyisosafrole in the mouse and its inactivity as a hepatocarcinogen relative to 1'-hydroxysafrole.
Boberg EW, Miller EC, Miller JA. PMID: 3757147
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