Quercetin (3,3',4',5,7-pentahydroxyflavone), a natural polyphenol isoflavonoid is believed to exhibit estrogenic and anticancer activity by acting as an effective radical-scavenger against oxidative cell damage. Various epidemiological studies have also shown that Quercetin and related isoflavonoids suppress cancerous tumor growth in vivo. However, the mechanism by which this occurs is not clearly understood. The mechanism of Quercetin as a potential endocrine disrupting chemical is herein investigated by focusing on its interactions with nucleic acid at the molecular level. Bulk electrolysis was utilized to induce the oxidation of Quercetin in real time and to study the chemistry of intermediate(s) formed. The oxidation products were further characterized using UV/Vis and fluorescence spectroscopy and Gas Chromatography with Mass Spectrometry. Results showed that the electrochemical oxidation of Quercetin produced quinoid intermediates in aqueous medium. The intermediates formed were found to be electrochemically and fluorescently active establishing the significance of the quinone chemistry. This work provides important information on the actual chemical behavior of quercetin in a biological media relative to that of a typical electrochemical environment.