Hematin-catalyzed epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by polyunsaturated fatty acid hydroperoxides.

Hematin catalyzes the epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene (BP-7,8-diol) by 13-hydroperoxy-9-cis,11-trans-octadecadienoic acid and other fatty acid hydroperoxides in the presence of detergent. The major oxidation product is the anti-dihydrodiolepoxide and the minor product is the syn-dihydrodiolepoxide. (+)-BP-7,8-diol is oxidized to (-)-anti-diolepoxide and (+)-syn-diolepoxide whereas (-)-BP-7,8-diol is oxidized to (+)-anti-diolepoxide and (-)-syn-diolepoxide.