Octocrylene

Octocrylene

Structural formula of octocrylene
Space-filling model of octocrylene
Names
IUPAC names 2-ethylhexyl 2-cyano-3,3- diphenyl-2-propenoate
Identifiers
CAS Number	6197-30-4 Y
ChEMBL	ChEMBL1201147 N
ChemSpider	21165 Y
Jmol 3D model	Interactive image
PubChem	22571
UNII	5A68WGF6WM Y
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
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/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

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, 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. 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). The only evidence suggesting a relationship between sunscreen and malignant melanoma is correlational, and thus cannot be used to establish a causal relationship.

See also

• Sunscreen controversy