3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||361.48 g/mol|
|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).
|what is ?)(|
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.
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.
In coral, octocrylene has been shown to accumulate in the form of fatty acid conjugates and trigger mitochondrial dysfunction. 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. 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. Earlier in 2019, the U.S. Virgin Island also banned the sale and use of oxybenzone, octinoxate, and octocrylene.
- Smart Skin Care: Octocrylene
- 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.
- 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" (PDF). Analytical Chemistry. 91 (1): 990–995. doi:10.1021/acs.analchem.8b04187. PMID 30516955.
- 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 (1): 944–951. doi:10.1021/acs.analchem.7b03996. hdl:21.11116/0000-0000-3212-3. PMID 29188988.
- 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 (5): 1227–1238. doi:10.1007/s00204-019-02408-7. PMID 30739143. S2CID 59622082.
- 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