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Octocrylene

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Organic compound
Octocrylene
Structural formula of octocrylene
Space-filling model of octocrylene
Names
Preferred IUPAC name 2-Ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
Other names Octocrylene
Octocrilene
Uvinul N-539
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.025.683 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3Key: FMJSMJQBSVNSBF-UHFFFAOYSA-N
  • InChI=1/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3Key: FMJSMJQBSVNSBF-UHFFFAOYAD
SMILES
  • N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
Properties
Chemical formula C24H27NO2
Molar mass 361.48 g/mol
Density 1.05 g/cm
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 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

  1. "Octocrylene - Chemical UVB+UVA sunscreen/sunblock agent". www.smartskincare.com.
  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. S2CID 13999532.
  3. 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.
  4. 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. Bibcode:2019ArTox..93.1227B. doi:10.1007/s00204-019-02408-7. PMID 30739143. S2CID 59622082.
  5. Downs, C. A.; DiNardo, Joseph C.; Stien, Didier; Rodrigues, Alice M. S.; Lebaron, Philippe (7 March 2021). "Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products". Chemical Research in Toxicology. 34 (4): 1046–1054. doi:10.1021/acs.chemrestox.0c00461. PMID 33682414.
  6. 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. S2CID 54567139.
  7. Republic of Palau. "RPPL No. 10-30: The Responsible Tourism Education Act of 2018 – PalauGov.pw". PalauGov.pw Your guide to finding and using Palau National Government services. Retrieved 16 October 2019.
  8. "Sustainable Travel in USVI". United States Virgin Islands. Archived from the original on 14 January 2024. Retrieved 17 February 2024. Avoid sunscreens that contain the "Toxic 3 Os" of oxybenzone, octinoxate and octocrylene – they are prohibited in the United States Virgin Islands. Wear rashguards, hats and use only non-nano mineral sunscreen containing zinc oxide and titanium dioxide, the only sunscreen ingredients deemed safe and effective by the FDA.
Sunscreening agents approved by the US FDA or other agencies
  • UVA: 400–315 nm
  • UVB: 315–290 nm
  • Chemical agents unless otherwise noted
UVA filters
UVB filters
UVA+UVB filters
See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn
Categories: