Removal of estrogenic activity and formation of oxidation products during ozonation of 17 alpha-ethinylestradiol

This study investigated the oxidation of the oral contraceptive 17alpha-ethinylestradiol (EE2) during ozonation. First, the effect of ozone (O-3) on the estrogenic activity of aqueous solutions of EE2 was studied using a yeast estrogen screen (YES). It could be shown that O-3 doses typically applied for the disinfection of drinking waters were sufficient to reduce estrogenicity by a factor of more than 200. However, it proved impossible to completely remove estrogenic activity due to the slow reappearance of 0.1 - 0.2% of the initial EE2 concentration after ozonation. Second, oxidation products formed during ozonation of EE2 were identified with LC-MS/MS and GC/MS and the help of the model compounds 5,6,7,8-tetrahydro-2-naphthol (THN) and 1-ethinyl-1-cyclohexanol (ECH),which represent the reactive phenolic moiety and the ethinyl group of EE2. Additionally, oxidation products of the natural steroid hormones 17beta-estradiol (E2) and estrone (E1) were identified. The chemical structures of the oxidation products were significantly altered as compared to the parent compounds, explaining the diminished estrogenic activity after ozonation. Overall, the results demonstrate that ozonation is a promising tool for the control of EE2, E2, and El in drinking water and wastewater.