Synthesis and characterization of hydroxylated polychlorinated biphenyls (PCBs) identified in human serum

Hydroxylated polychlorinated biphenyls (PCBs) have been identified in wildlife and human samples. Most of these compounds are highly chlorinated (penta-hepatachloro) and contain a single meta- or para-hydroxyl group. Using the Cadogan coupling procedure, the following hydroxy-PCBs congeners were synthesized: 2,3,3′,4′,5- pentachloro-4-biphenylol, 2,3′,4,4′,5-pentachloro-3-biphenylol, 2′,3,3′,4′,5-pentachloro-4-biphenylol, 2,2′,3′,4,4′-pentachloro-3-biphenylol, 2,2′,3,3′,4′,5-pentachloro-4-biphenylol, 2,2′,3′,4,4′,5-hexachloro-3-biphenylol, 2,2′,3,4′,5,5′-hexachloro-4-biphenylol, 2,2′,3,3′,4′,5,5′-heptachloro-4-biphenylol, 2,2′,3′,4,4′,5,5′-heptachloro-3-biphenylol, 2,2′,3,4′,5,5′,6-heptachloro-4-biphenylol. Many of these compounds have been detected as residues in human serum and current studies are investigating their activities as agonists and antagonists for several endocrine-mediated responses.