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

Isabella Karlsson ; Elin Persson ; Jerker Mårtensson (Institutionen för kemi- och bioteknik, Organisk kemi) ; Anna Börje
Photochemistry and Photobiology (0031-8655). Vol. 88 (2012), 4, p. 904-912.
[Artikel, refereegranskad vetenskaplig]

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.

Nyckelord: photoallergic contact-dermatitis, consecutive patients, tiaprofenic, acid, ketoprofen, photosensitization, benzophenone, reactivity, skin, photostability, irradiation



Denna post skapades 2012-08-09. Senast ändrad 2012-08-13.
CPL Pubid: 161330

 

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Institutioner (Chalmers)

Institutionen för kemi och molekylärbiologi (GU)
Institutionen för kemi- och bioteknik, Organisk kemi (2006-2014)

Ämnesområden

Organisk kemi
Biokemi och molekylärbiologi

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