Octocrylene
| Octocrylene | |
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2-ethylhexyl 2-cyano-3,3- |
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| Identifiers | |
| CAS number | 6197-30-4  |
| PubChem | 22571 |
| ChemSpider | 21165 |
| UNII | 5A68WGF6WM |
| ChEMBL | CHEMBL1201147  |
| Jmol-3D images | Image 1 |
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| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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)
[edit] See also
[edit] 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.
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