Formation of the 1,2-diol as a metabolite of 7,12-dimethylbenz[a]anthracene by rodent and human skin

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Abstract
Rodent and human skin maintained in short-term organ culture was treated with 3H-labeled 7,12-dimethylbenz[a]anthracene. Extracts of the rodent tissue and culture fluid in which either mouse, rat or human skin had been maintained contained radioactive material that possessed the chromatographic characteristics of trans-1,2-dihydro-1,2-dihydroxy-7,12-dimethylbenz[a]anthracene when it was examined in 2 different HPLC [high performance liquid chromatography] systems. When the metabolite was treated with hot mineral acid, the 2 radioactive products formed co-chromatographed with the phenols that were formed when the reference dihydrodiol was similarly treated. Acetylation of the isolated metabolite yielded a single product that had chromatographic properties identical to those of the diacetate of the reference dihydrodiol. The 1,2-dihydrodiol of 7,12-dimethylbenz[a]anthracene is formed as a metabolite of this hydrocarbon by rodent and human skin maintained in short-term organ culture.

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