TY - JOUR
T1 - Synthesis of two novel flavonoid derivatives with extended φ-system
T2 - Possible UV-B and UV-A sunscreens
AU - Al-Busafi, Saleh N.
AU - Al-Buraiki, Asma M.
AU - Al-Qarni, Monther H.
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
KW - Baker-Venkataraman rearrangement
KW - Bathochromic shit.
KW - Flavonoids
KW - Sunscreens
KW - UV-visible absorption
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U2 - 10.14233/ajchem.2017.20430
DO - 10.14233/ajchem.2017.20430
M3 - Article
AN - SCOPUS:85015435369
SN - 0970-7077
VL - 29
SP - 1103
EP - 1107
JO - Asian Journal of Chemistry
JF - Asian Journal of Chemistry
IS - 5
ER -