O-Demethyl Dihydroxy Elemicin

O-demethyl dihydroxy elemicin is detectable in human urine as the primary metabolite of elemicin following the ingestion of nutmeg.[1] This compound has no known route to alkaloid formation in animals or humans. It's not currently known for certain how this metabolite forms. It is likely a metabolite created sometime after elemicin forms the metabolite methoxyeugenol.

Chemical Properties

CAS No. 22805-15-8
IUPAC Name: 3-(4-hydroxy-3,5-dimethoxyphenyl)propane-1,2-diol
Synonyms: 3-(3,5-Dimethoxy-4-hydroxyphenyl)-1,2-propanediol; 3-(4-Hydroxy-3,5-dimethoxyphenyl)-1,2-propanediol
PubChem Compound ID: 71307316
Molecular Weight: 228.24174 g/mol
Molecular Formula: C11H16O5
XLogP3: 0.5
H-Bond Donor: 3
H-Bond Acceptor: 5
InChIKey: IMVVRJZYFJNFBX-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1O)OC)CC(CO)O
InChI: InChI=1S/C11H16O5/c1-15-9-4-7(3-8(13)6-12)5-10(16-2)11(9)14/h4-5,8,12-14H,3,6H2,1-2H3
Solubility: Unknown.
Physical Description: White solid

Bibliography

1. Ther Drug Monit. 2006 Aug;28(4):568-75.

Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. Beyer J, Ehlers D, Maurer HH; Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, University of Saarland, Homburg (Saar), Germany; PubMed PMID: 16885726