Photodecomposition of several compounds commonly used as sunscreen agents

Abstract

Abstract The photolysis reactions of three compounds commonly used as a sunscreen agents, Parsol 1789 (1-[4-(1,1-dimethylethyl)phenyl]-3-(4-methoxyphenyl)-1,3- propanedione), Oxybenzone ((2-hydroxy-4-methoxyphenyl)phenyl-methanone) and Padimate O (2-ethylhexyl-4-(dimethylamino)benzoate), were investigated to provide a chemical background to aid in the understanding of the photosensitization of the sunscreen agents. Photolysis was carried out in cyclohexane for 70–140 h using a mercury vapor lamp (450W) without excluding oxygen. Irradation of Parsol 1789 in cyclohexane yielded tert -butylbenzene, p - tert -butylbenzoic acid and p -methoxybenzoic acid; products obtained from the combination of the sunscreen with the solvent included the cyclohexyl esters of p -methoxybenzoic acid, p - tert -butylbenzoic acid and methanoic acid; products obtained from the solvent included cyclohexanol, cyclohexanone and dicyclohexyl ether. Irradiation of Oxybenzone in the cyclohexane for 100 h produced no detectable products by either gas or liquid chromatographic analysis. Oxybenzone was recovered unchanged and no products were observed from the photoinitiated reaction of oxygen with the solvent. Irradiation of Padimate O in cyclohexane yielded the ethylhexyl esters of p -aminobenzoic acid, p -monomethylaminobenzoic acid and p -dimethylamino ( o/m )-methylbenzoic acid, as well as products from the photoinitiated reaction of oxygen with the solvent.