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Octocrylene

Organic compound

Summary

Organic compound

Octocrilene Uvinul N-539

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the Knoevenagel condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous, oily liquid that is clear and colorless.

The extended conjugation of the acrylate portion of the molecule absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths from 280 to 320 nm, protecting the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.

Safety

Octocrylene can penetrate into the skin where it acts as a photosensitizer, resulting in an increased production of free radicals under illumination. It may also pass through the skin, into the blood stream, eventually being metabolized and excreted in urine in form of its metabolites. Octocrylene can convert to benzophenone through a retro-aldol condensation. The reaction occurs slowly over time, yielding significant concentration of benzophenone in all commercial cosmetics tested formulated with octocrylene.

In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and probably trigger mitochondrial dysfunction.

Regulation

Palau has banned the sale and use of three reef-toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018. The United States Virgin Islands has also banned the use of sunscreens containing octocrylene, requiring that all visitors use "non-nano mineral sunscreen" containing zinc oxide and titanium dioxide.

References

References

  1. "Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent".
  2. (2006). "Sunscreen enhancement of UV-induced reactive oxygen species in the skin". Free Radical Biology and Medicine.
  3. (2018). "Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS". Analytical Chemistry.
  4. (2019). "Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure". Archives of Toxicology.
  5. (7 March 2021). "Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products". Chemical Research in Toxicology.
  6. (2019). "Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction". Analytical Chemistry.
  7. "RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw".
  8. "Sustainable Travel in USVI".
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

cyanoacetate-esters household-chemicals sunscreening-agents 2-ethylhexyl-esters
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