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Vol. 29 No. 5 (2017): Vol 29 Issue 5

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Synthesis of Two Novel Flavonoid Derivatives with Extended p-System: Possible UV-B and UV-A Sunscreens

https://doi.org/10.14233/ajchem.2017.20430
Saleh N. Al-Busafi
Department of Chemistry, College of Science, Sultan Qaboos University, Box 36, Al-Khodh 123, Sultanate of Oman
Asma M. Al-Buraiki
Department of Chemistry, College of Science, Sultan Qaboos University, Box 36, Al-Khodh 123, Sultanate of Oman
Monther H. Al-Qarni
Department of Chemistry, College of Science, Sultan Qaboos University, Box 36, Al-Khodh 123, Sultanate of Oman

Corresponding Author(s) : Saleh N. Al-Busafi

saleh1@squ.edu.om

Asian Journal of Chemistry, Vol. 29 No. 5 (2017): Vol 29 Issue 5

Abstract

Two novel flavonoid derivatives 5 and 6 were synthesized and characterized by IR, 1H, 13C NMR spectroscopy and mass spectrometry. The core structure of the two flavonoids was constructed by applying Baker-Venkataraman rearrangement on 2-acylphenyl ester intermediate. The two compounds exhibited remarkable UV-visible absorption activities compared to flavone. Flavonoid 5 showed a bathochromic shift of 75.6 nm when the size of the cinnamic acid was increased by phenylbutadienyl group and hence it is a good UVA sunscreen. The 4-nitrostyryl group introduced in the cinnamic acid subchromophore of flavonoid 6 causes the compound to absorb at 308.3 and at 345.8 nm which will make it a broad-spectrum sunscreen.

Keywords

Flavonoids Baker-Venkataraman rearrangement UV-visible absorption Sunscreens Bathochromic shit
Al-Busafi, S. N., Al-Buraiki, A. M., & Al-Qarni, M. H. (2017). Synthesis of Two Novel Flavonoid Derivatives with Extended p-System: Possible UV-B and UV-A Sunscreens. Asian Journal of Chemistry, 29(5), 1103–1107. https://doi.org/10.14233/ajchem.2017.20430
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