Octocrylene

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the reaction of 3,3-diphenylcyanoacrylate with 2-ethylhexanol. It is a viscous, oily liquid that is clear and colorless.

Octocrylene
Names
IUPAC name
2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate
Other names
Octocrylene
Octocrilene
Uvinul N-539
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.025.683
UNII
Properties
C24H27NO2
Molar mass 361.48 g/mol
Density 1.05 g/cm3
Melting point 14 °C (57 °F; 287 K)
Boiling point 218 °C (424 °F; 491 K) at 1.5 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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,[1] protecting the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, adding emollient and oil-like (water resistant) properties.

This organic compound can penetrate into the skin where it acts as a photosensitizer. This results in an increased production of free radicals under illumination.[2]

In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and trigger mitochondrial dysfunction.[3] Also, it has been demonstrated that octocrylene passes through the skin in human experiments, enters blood stream, is metabolized and eventually excreted in urine in form of its metabolites.[4][5] The country of Palau banned the sale and use of 3 reef toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018.[6] Earlier in 2019, the U.S. Virgin Island also banned the sale and use of oxybenzone, octinoxate, and octocrylene.

See also
  • Sunscreen controversy


References
  1. Smart Skin Care: Octocrylene
  2. Hanson Kerry M.; Gratton Enrico; Bardeen Christopher J. (2006). "Sunscreen enhancement of UV-induced reactive oxygen species in the skin". Free Radical Biology and Medicine. 41 (8): 1205–1212. doi:10.1016/j.freeradbiomed.2006.06.011. PMID 17015167.
  3. Stien, Didier; Clergeaud, Fanny; Rodrigues, Alice M.S.; Lebaron, Karine; Pillot, Rémi; Romans, Pascal; Fagervold, Sonja; Lebaron, Philippe (2019). "Metabolomics reveal that octocrylene accumulates in Pocillopora damicornis tissues as fatty acid conjugates and triggers coral cell mitochondrial dysfunction". Analytical Chemistry. 91: 990-995. doi:10.1021/acs.analchem.8b04187.
  4. Bury, Daniel; Belov, Vladimir N.; Qi, Yulin; Hayen, Heiko; Volmer, Dietrich A.; Brüning, Thomas; Koch, Holger M. (2018). "Determination of urinary metabolites of the emerging UV filter octocrylene by online-SPE-LC-MS/MS". Analytical Chemistry. 90: 944-951. doi:10.1021/acs.analchem.7b03996. hdl:21.11116/0000-0000-3212-3.
  5. Bury, Daniel; Modick-Biermann, Hendrik; Leibold, Edgar; Brüning, Thomas; Koch, Holger M. (2019). "Urinary metabolites of the UV filter octocrylene in humans as biomarkers of exposure". Archives of Toxicology. 93: 1227-1238. doi:10.1007/s00204-019-02408-7.
  6. Republic of Palau. PalauGov.pw Your guide to finding and using Palau National Government services https://www.palaugov.pw/documents/rppl-no-10-30-the-responsible-tourism-education-act-of-2018/. Retrieved 16 October 2019. Missing or empty |title= (help)
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