Studies in detoxication. 73. The metabolism of alkylbenzenes: phenylacetylene and phenylethylene (styrene)

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Abstract
The metabolic fate of phenylethylene (styrene) and phenylacetylene in the rabbit was investigated. Phenylacetylene is slowly metabolized to phenaceturic acid, which is excreted in the urine for several days after a single oral dose (0.4 g/kg). Roughly 30-40% of the dose is eliminated in the unchanged state in the expired air over 3 days, and about the same amount is excreted in the urine as phenaceturic acid. Phenylacetylene probably is asymmetrically hydrated in vivo to the enol form of phenacetaldehyde. Styrene does not yield phenaceturic acid in vivo. Its main metabolite is hippuric acid (30-40% of the dose). It also forms mandelic acid and phenylglycol, the latter being excreted as a monoglucuronide. Only about 2% of the styrene administered is eliminated unchanged in the expired air. DL-phenylglycol when fed to rabbits also yields hippuric acid, mandelic acid and phenylglycol glucuronide, and it appears to be an intermediate in the metabolism of styrene. Styrene may undergo "perhydroxylation" in vivo to phenylglycol. Styrene epoxide and methylphenylcarbinol, which are possible intermediates in styrene metabolism, do not lead to the excretion of phenylglycol when administered to rabbits although they yield hippuric and mandelic acids. Phenacyl alcohol is not reduced to phenylglycol in the rabbit. A small proportion ( < 5%) of it appears to be excreted as phenacyl alcohol glucuronide, which was isolated.

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