3-(3,4,5-Trimethoxyphenyl)propane-1,2-diol

3-(3,4,5-trimethoxyphenyl)propane-1,2-diol is an elemicin metabolite found in rat urine.

The major metabolic reactions in rats of elemicin follow the cinnamoyl pathway or the epoxide-diol pathway. The cinnamoyl pathway gives 3-(3,4,5-Trimethoxyphenyl)propionic acid and its glycine conjugate as major metabolites. The epixide-diol pathway gives 3-(3,4,5-trimethoxyphenyl)propane-1,2-diol as a major metabolite.[1]

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Chemical Properties

Synonyms: kmeriol; dihydroxy elemicin; 2,3-dihydroxy elemicin
PubChem Compound ID: 129913
Molecular Weight: 242.26832 [g/mol]
Molecular Formula: C12H18O5
XLogP3: 0.4
IUPAC Name: 3-(3,4,5-trimethoxyphenyl)propane-1,2-diol
InChI: InChI=1S/C12H18O5/c1-15-10-5-8(4-9(14)7-13)6-11(16-2)12(10)17-3/h5-6,9,13-14H,4,7H2,1-3H3
InChIKey: SNDFRVPKIVPGED-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC(=C1OC)OC)CC(CO)O

Bibliography

1. Xenobiotica. 1980 May;10(5):371-80.

Metabolism of alkenebenzene derivatives in the rat. III. Elemicin and isoelemicin. Solheim E, Scheline RR; PubMed PMID 7415220