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Octocrylene

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.025.683Edit this at Wikidata
UNII
  • 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,3-5,12,18H2,1-2H3 checkY
    Key: FMJSMJQBSVNSBF-UHFFFAOYSA-N checkY
  • 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,3-5,12,18H2,1-2H3
    Key: FMJSMJQBSVNSBF-UHFFFAOYAD
  • N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
Properties
C24H27NO2
Molar mass361.48 g/mol
Density1.05 g/cm3
Melting point14 °C (57 °F; 287 K)
Boiling point218 °C (424 °F; 491 K) at 1.5 mmHg
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Octocrylene is anorganic compound used as an ingredient insunscreens and cosmetics. It is anester formed by theKnoevenagel condensation of 2-ethylhexyl cyanoacetate withbenzophenone. It is a viscous, oily liquid that is clear and colorless.

The extendedconjugation of theacrylate portion of the molecule absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths from 280 to 320 nm,[1] protecting the skin fromdirect DNA damage. The ethylhexanol portion is afatty alcohol, addingemollient and oil-like (water resistant) properties.

Safety

[edit]

Octocrylene can penetrate into the skin where it acts as aphotosensitizer, resulting in an increased production of free radicals under illumination.[2] It may also pass through the skin, into the blood stream, eventually being metabolized and excreted in urine in form of its metabolites.[3][4] Octocrylene can convert tobenzophenone through a retro-aldol condensation.[5] 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.[6]

Regulation

[edit]

Palau has banned the sale and use of three reef-toxic UV filters including octocrylene in its Responsible Tourism Education Act of 2018.[7] TheUnited 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.[8]

References

[edit]
  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. Retrieved16 October 2019.
  8. ^"Sustainable Travel in USVI".United States Virgin Islands. Archived fromthe original on 14 January 2024. Retrieved17 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 agentsapproved by theUS FDA or other agencies
  • UVA: 400–315 nm
  • UVB: 315–290 nm
  • Chemical agents unless otherwise noted
UVA filters
UVB filters
UVA+UVB filters
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