Synthesis of two novel flavonoid derivatives with extended φ-system

Possible UV-B and UV-A sunscreens

Saleh N. Al-Busafi, Asma M. Al-Buraiki, Monther H. Al-Qarni

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)1103-1107
Number of pages5
JournalAsian Journal of Chemistry
Volume29
Issue number5
DOIs
Publication statusPublished - 2017

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Sun hoods
Flavonoids
Derivatives
flavone
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Esters
cinnamic acid

Keywords

  • Baker-Venkataraman rearrangement
  • Bathochromic shit.
  • Flavonoids
  • Sunscreens
  • UV-visible absorption

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of two novel flavonoid derivatives with extended φ-system : Possible UV-B and UV-A sunscreens. / Al-Busafi, Saleh N.; Al-Buraiki, Asma M.; Al-Qarni, Monther H.

In: Asian Journal of Chemistry, Vol. 29, No. 5, 2017, p. 1103-1107.

Research output: Contribution to journalArticle

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