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Abstract
1. The metabolism of eugenol (4-hydroxy-3-methoxy-allylbenzene) was investigated in
male and female healthy volunteers. It was rapidly absorbed and metabolized after
oral administration and was almost completely excreted in the urine within 24 h. Unmetabolized
eugenol excreted in urine amounted to less than 0.1% of the dose. 2. The urine contained
conjugates of eugenol and of nine metabolites. The structures of these metabolites,
elucidated using g.l.c.-mass spectrometry, and by comparison with synthetic reference
compounds, were identified as: eugenol, 4-hydroxy-3-methoxyphenyl-propane, cis- and
trans-isoeugenol, 3-(4-hydroxy-3-methoxyphenyl)-propylene-1,2-oxide, 3-(4-hydroxy-3-methoxyphenyl)-propane-1,2-diol,
and 3-(4-hydroxy-3-methoxyphenyl)-propionic acid. 3. The structures of the following
metabolites were tentatively deduced from mass spectra only, as reference compounds
were not available: 3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-allylbenzene, 3-(6?-mercapto-4-hydroxy-3-methoxyphenyl)-propane,
and 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-propionic acid. 4. The amounts of the
individual metabolites excreted were determined by g.l.c. Some 95% of the dose was
recovered in the urine, most of which (greater than 99%) consisted of phenolic conjugates;
50% of the conjugated metabolites were eugenol-glucuronide and sulphate. Other metabolic
routes observed were the epoxide-diol pathway, synthesis of a thiophenol and of a
substituted propionic acid, allylic oxidation, and migration of the double bond.