Octocrylene

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Octocrylene
Octocrylene
Identifiers
CAS number 6197-30-4 YesY
PubChem 22571
ChemSpider 21165 YesY
UNII 5A68WGF6WM YesY
ChEMBL CHEMBL1201147 N
Jmol-3D images Image 1
Properties
Molecular 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 noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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)[weasel words][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.

See also[edit]

References[edit]

  1. ^ Smart Skin Care: Octocrylene
  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.