Unexpected transformation of dissolved phenols to toxic dicarbonyls by hydroxyl radicals and UV light

Significance Phenols are common anthropogenic and natural chemicals that contaminate drinking water sources. To reduce exposure to these compounds, hydroxyl radicals are often used as chemical oxidants during water treatment. Although this treatment process removes phenols, we have found that it unexpectedly produces toxic transformation products. We identify these products and simultaneously assess their toxicity with a technique that detects products formed when the transformation products react with amino acids and peptides. Our results highlight the potential risks of using oxidative treatment on alternative drinking water sources, such as contaminated groundwater and recycled municipal wastewater. They also suggest that these reactions produce these toxic transformation products in other situations, including in clouds and sunlit surface waters and within living cells.