Synthesis of Bisphenol A Quinones Using 2-Iodoxybenzoic Acid (IBX)

Bisphenol A (BPA) has been identified to have estrogenic properties and, like estrogen, can cause DNA damage when metabolized (Cavalieri and Rogan, 2010). The metabolism of BPA involves hydroxylation of one of its two symmetrical benzene rings to catechol, which is subsequently oxidized to quinone. Estrogen is metabolized in a similar manner and estrogen quinones have been linked to breast and other human cancers. In this project, we investigate the synthesis of BPA quinones using 2-iodoxybenzoic acid (IBX). While IBX has been used to form estrogen quinones from estrogen, it has not been previously used to make BPA quinones. Since BPA contains two symmetrical phenol groups, we demonstrated that control of the amount of IBX can lead to either the mono- or the diquinone structures (Figure 1). The reaction and the isolation of either the mono- or the diquinone has been achieved. The products of the oxidations can be isolated in their quinone form or the quinones can be reduced to mono- or dicatechols. Quinone and catechol products were fully characterized by 1H and 13C NMR. The facile production of either the mono- or the diquinones of BPA will allow reactions with biological nucleophiles such as DNA bases and amino-containing proteins to isolated biomarkers of BPA damage caused from either mono or diquinones. In addition, knowledge of BPA quinone chemistry can aid us to understand the mechanism of the BPA carcinogenicity, which, subsequently, leads to development of regulation methods of BPA