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Investigation of the sunscreen octocrylene's interaction with amino acid analogs in the presence of UV radiation.

Photochemistry and photobiology (2012-03-21)
Isabella Karlsson, Elin Persson, Jerker Mårtensson, Anna Börje
ABSTRACT

Octocrylene is an organic UV filter, commonly used in sunscreens and cosmetics, which can give rise to both contact and photocontact allergy. Our aim was to investigate octocrylene's interaction with amino acid analogs in the presence of UV radiation to better understand the reason for octocrylene's photoallergenic capacity. The amino acid analogs were photolysed in presence and absence of octocrylene for 1 h in cyclohexane. The rate of degradation was considerably slower for all amino acid analogs when octocrylene was present in the mixture. Benzylamine, the lysine analog, did react with octocrylene during the photolysis and the corresponding amide was formed in an acylation reaction. By varying the benzylamine concentration and keeping the octocrylene concentration fixed the reaction rate was shown to be independent of the amine concentration. The same type of acylation reaction took place when octocrylene alone was photolysed in ethanol in which the ethyl ester was formed from octocrylene and ethanol. Our results suggest that octocrylene's ability to cause photocontact allergy could be due to its photoinduced reactivity toward primary amines and alcohols.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzylamine, ReagentPlus®, 99%
Supelco
Octocrylene, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
1-Octanethiol, ≥98.5%
Sigma-Aldrich
3-Methylindole, 98%
Sigma-Aldrich
Skatole, ≥98%
Supelco
Benzylamine, for GC derivatization, LiChropur, ≥99.0%
Sigma-Aldrich
Benzylamine, purified by redistillation, ≥99.5%
Supelco
Octocrylene, analytical standard
Sigma-Aldrich
2-Ethylhexyl 2-cyano-3,3-diphenylacrylate, 97%
Sigma-Aldrich
Benzylamine hydrochloride
Sigma-Aldrich
4-Propylphenol, 99%

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