Investigation of the Sunscreen Octocrylene's Interaction with Amino Acid Analogs in the Presence of UV Radiation
Journal article, 2012

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 octocrylenes interaction with amino acid analogs in the presence of UV radiation to better understand the reason for octocrylenes 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 octocrylenes ability to cause photocontact allergy could be due to its photoinduced reactivity toward primary amines and alcohols.

benzophenone

irradiation

photoallergic contact-dermatitis

reactivity

photosensitization

photostability

ketoprofen

acid

consecutive patients

skin

tiaprofenic

Author

I. Karlsson

University of Gothenburg

Elin Persson

University of Gothenburg

Jerker Mårtensson

Chalmers, Chemical and Biological Engineering, Organic Chemistry

Anna Börje

University of Gothenburg

Photochemistry and Photobiology

0031-8655 (ISSN)

Vol. 88 4 904-912

Subject Categories

Biochemistry and Molecular Biology

Organic Chemistry

DOI

10.1111/j.1751-1097.2012.01142.x

More information

Created

10/8/2017