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

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 organ...

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Bibliographic Details
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
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Summary: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.
ISSN:2050-7887
2050-7895
DOI:10.1039/c7em00059f