Photolysis and cellular toxicities of the organic ultraviolet filter chemical octyl methoxycinnamate and its photoproducts

• Published in: Environmental science--processes & impacts 2017-06, Vol.19 (6), p.851-860
• Main Authors: Stein, Hannah V, Berg, Courtney J, Maung, Jessica N, O'Connor, Lauren E, Pagano, Alexandra E, MacManus-Spencer, Laura A, Paulick, Margot G
• Format: Article
• Language: English
• Subjects: Animals; Cell Culture Techniques; Cell Survival - drug effects; Cinnamates - chemistry; Cinnamates - radiation effects; Cinnamates - toxicity; Humans; Mice; NIH 3T3 Cells; Photolysis; Skin - drug effects; Skin - radiation effects; Stereoisomerism; Sunscreening Agents - chemistry; Sunscreening Agents - radiation effects; Sunscreening Agents - toxicity; Ultraviolet Rays
• ISSN: 2050-7887; 2050-7895
• DOI: 10.1039/c7em00059f

Organic ultraviolet filter chemicals (UVFCs) are the active ingredients used in many sunscreens to protect the skin from UV light; these chemicals have been detected in numerous aquatic environments leading to concerns about how they might affect aquatic organisms and humans. One commonly used organic UVFC is octyl methoxycinnamate (OMC), better known by its commercial name, octinoxate. Upon exposure to UV light, OMC degrades rapidly, forming numerous photoproducts, some of which have been previously identified. In this study, we isolated and completely characterized the major products of OMC photolysis, including the two major stable OMC cyclodimers. One of these cyclodimers is a δ-truxinate, resulting from a head-to-head dimerization of two OMC molecules, and the other cyclodimer is an α-truxillate, resulting from a head-to-tail dimerization of two OMC molecules. Additionally, the cellular toxicities of the individual photoproducts were determined; it was found that the parent UVFC, OMC, 4-methoxybenzaldehyde, and two cyclodimers are significantly toxic to cells. The photoproduct 2-ethylhexanol is not cytotoxic, demonstrating that different components of OMC photolysate contribute differently to its cellular toxicity. This study thus provides an enhanced understanding of OMC photolysis and gives toxicity data that can be used to better evaluate OMC as a sunscreen agent.