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Benchmark studies of UV–vis spectra simulation for cinnamates with UV filter profile

  • Ricardo D’A. Garcia
  • Vinícius G. Maltarollo
  • Káthia M. Honório
  • Gustavo H. G. TrossiniEmail author
Original Paper

Abstract

Skin cancer is a serious public health problem worldwide, being incident over all five continents and affecting an increasing number of people. As sunscreens are considered an important preventive measure, studies to develop better and safer sunscreens are crucial. Cinnamates are UVB filters with good efficiency and cost-benefit, therefore, their study could lead to the development of new UV filters. A benchmark to define the most suitable density functional theory (DFT) functional to predict UV–vis spectra for ethylhexyl methoxycinnamate was performed. Time-dependent DFT (TD-DFT) calculations were then carried out [B3LYP/6-311 + G(d,p) and B3P86/6-311 + G(d,p) in methanol environment] for seven cinammete derivatives implemented in the Gaussian 03 package. All DFT/TD-DFT simulations were performed after a conformational search with the Monte-Carlo method and MMFF94 force field. B3LYP and B3P86 functionals were better at reproducing closely the experimental spectra of ethylhexyl methoxycinnamate. Calculations of seven cinnamates showed a λmax of around 310 nm, corroborating literature reports. It was observed that the energy for the main electronic transition was around 3.95 eV and could be explained by electron delocalization on the aromatic ring and ester group, which is important to UV absorption. The methodology employed proved to be suitable for determination of the UV spectra of cinnamates and could be used as a tool for the development of novel UV filters.

Keywords

Cinnamates TD-DFT Molecular modeling UV filters UV spectra simulation 

Notes

Acknowledgments

The authors would like to thank FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo), CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) and CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) for financial support.

Supplementary material

894_2015_2689_MOESM1_ESM.docx (1.8 mb)
ESM 1 (DOCX 1871 kb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  • Ricardo D’A. Garcia
    • 1
  • Vinícius G. Maltarollo
    • 1
  • Káthia M. Honório
    • 2
    • 3
  • Gustavo H. G. Trossini
    • 1
    Email author
  1. 1.Department of Pharmacy, Faculty of Pharmaceutical SciencesUniversity of São PauloSão PauloBrazil
  2. 2.School of Arts, Sciences and HumanitiesUniversity of São PauloSão PauloBrazil
  3. 3.Center of Natural and Human SciencesFederal University of ABCSanto AndréBrazil

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