caa a22 4500 60551173X CHVBK 20210128100652.0 cr unu---uuuuu 210128e20151201xx s 000 0 eng 10.1007/s00894-015-2863-2 doi (NATIONALLICENCE)springer-10.1007/s00894-015-2863-2 Theoretical study of tautomers and photoisomers of avobenzone by DFT methods [Elektronische Daten] [Gustavo Trossini, Vinicius Maltarollo, Ricardo Garcia, Claudinéia Pinto, Maria Velasco, Kathia Honorio, André Baby] Organic ultraviolet (UV) filters such as cinnamates, benzophenones, p-aminobenzoic derivatives, and avobenzone (which have well-established and recognized UV-filtering efficacies) are employed in cosmetic/pharmaceutical products to minimize the harm caused by exposure of the skin to sunlight. In this study, a detailed investigation of the photostability and tautomerism mechanisms of avobenzone was performed utilizing DFT methods. The UV spectral profile of avobenzone was also simulated, and the results showed good agreement with experimental data. Furthermore, the calculations were able to distinguish tautomers and photoisomers of the studied organic filter based on their properties, thus showing the potential to develop new organic UV filters. Graphical Abstract Theoretical studies of avobenzone and its tautomers by TD-DFT. Springer-Verlag Berlin Heidelberg, 2015 Avobenzone nationallicence Photostability nationallicence Tautomerism nationallicence Molecular modeling nationallicence DFT methods nationallicence Trossini Gustavo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Maltarollo Vinicius Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Garcia Ricardo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Pinto Claudinéia Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Velasco Maria Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Honorio Kathia School of Arts, Sciences and Humanities, University of São Paulo, São Paulo, São Paulo, Brazil aut Baby André Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut Journal of Molecular Modeling Springer Berlin Heidelberg 21/12(2015-12-01), 1-7 1610-2940 21:12<1 2015 21 894 https://doi.org/10.1007/s00894-015-2863-2 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00894-015-2863-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Trossini Gustavo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Maltarollo Vinicius Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Garcia Ricardo Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Pinto Claudinéia Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Velasco Maria Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 700 1- Honorio Kathia School of Arts, Sciences and Humanities, University of São Paulo, São Paulo, São Paulo, Brazil aut NATIONALLICENCE 700 1- Baby André Department of Pharmacy, Faculty of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 580, 05508-000, São Paulo, SP, Brazil aut NATIONALLICENCE 773 0- Journal of Molecular Modeling Springer Berlin Heidelberg 21/12(2015-12-01), 1-7 1610-2940 21:12<1 2015 21 894