Octocrylene

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Octocrylene

IUPAC name 2-ethylhexyl 2-cyano-3,3- diphenyl-2-propenoate
Identifiers
CAS number	6197-30-4^Y
PubChem	22571
ChemSpider	21165^Y
UNII	5A68WGF6WM^Y
ChEMBL	CHEMBL1201147^N
Jmol-3D images	Image 1
SMILES N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
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,3-5,12,18H2,1-2H3^Y Key: FMJSMJQBSVNSBF-UHFFFAOYSA-N^Y 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
Properties
Molecular formula	C₂₄H₂₇NO₂
Molar mass	361.48 g/mol
Density	1.05 g/cm³
Melting point	14 °C
Boiling point	218 °C at 1.5 mmHg
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the condensation of a 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,^[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] Free radicals are known to induce indirect DNA damage, and an increased concentration of free radicals might have contributed to the increased incidence of malignant melanoma in sunscreen-users compared to non-users (see Epidemiology of malignant melanoma)^{[citation needed]}. The only evidence suggesting a relationship between sunscreen and malignant melanoma is correlational, and thus cannot be used to establish a causal relationship.

References

↑ 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.

v t e 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	Avobenzone (Parsol 1789) Bisdisulizole disodium (Neo Heliopan AP) Diethylamino hydroxybenzoyl hexyl benzoate (Uvinul A Plus) Ecamsule (Mexoryl SX) Methyl anthranilate

UVB filters	4-Aminobenzoic acid (PABA) Cinoxate Ethylhexyl triazone (Uvinul T 150) Homosalate 4-Methylbenzylidene camphor (Parsol 5000) Octyl methoxycinnamate (Octinoxate) Octyl salicylate (Octisalate) Padimate O (Escalol 507) Phenylbenzimidazole sulfonic acid (Ensulizole) Polysilicone-15 (Parsol SLX) Trolamine salicylate

UVA+UVB filters	Bemotrizinol (Tinosorb S) Benzophenones 1–12 Dioxybenzone Drometrizole trisiloxane (Mexoryl XL) Iscotrizinol (Uvasorb HEB) Octocrylene Oxybenzone (Eusolex 4360) Sulisobenzone hybrid (chemical/physical): Bisoctrizole (Tinosorb M) physical: Titanium dioxide, Zinc oxide

See also: Photoprotection Sunburn Sun protective clothing

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Octocrylene

See also

References