Octocrylene

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous, oily liquid that is clear and colorless.

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 InfoCard 100.025.683
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 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
  • N#C/C(C(=O)OCC(CC)CCCC)=C(/c1ccccc1)c2ccccc2
Properties
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

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.

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