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In order to enhance the water-solubility and biological utilization rate of chrysin, sodium 5,7-dihydroxylflavone-8-sulfonate (1, [Na(H2O) 1/2]X, X = C15H9O4SO3, 5,7-dihydroxylfla- vone-8-sulfonate) was synthesized and its structure was identified on the basis of NMR, FT-IR and elemental analysis. The assembly of 5,7-dihydroxylflavone-8-sulfonate with diethylamide cation afforded diethylamide 5,7-dihydroxylflavone-8-sulfonate (2, NH2(CH2CH 3)2X) which was characterized by FT-IR and elemental analysis. The crystal structures of 1 and 2 were determined by X-ray single-crystal diffraction analysis. The crystal of 1 is of triclinic system, space group P1̄, with a = 8.5628(13), b = 12.8916(19), c = 13.562(2) Å, a = 82.494(1), β = 78.601(2), γ = 84.033(2)°, C 30H20Na2OI5S2, Z= 2, Mr = 730.59, V= 1450.3(4) Å3, Dc = 1.673 g/cm3, F(000) = 748,μ = 0.295 mm-1, the final R = 0.0641 and wR = 0.1458. The crystal of 2 crystallizes in the triclinic system, space group P1̄, with a = 7.689(2), b = 11.184(3), c = 11.734(3) Å, α = 74.268(3), β = 81.751(4), γ = 87.991(3)°, C19H21NO7S, 2 = 2, M r= 407.43, V= 961.2(4) Å3, Dc = 1.408 g/cm3, P(000) = 428, μ = 0.210 mm-1, the final R = 0.0484 and wR = 0.1195. In 1, the three-dimensional structure is organized into organic and inorganic regions; the flavone skeletons are stacked into organic regions by π π stacking interactions; inorganic regions are generated by Na-O coordination bonds among sulfonate groups, coordinated water molecules and Na1. The sulfonate groups play an important role as a bridge of inorganic and organic regions. One-dimensional chain structure of 2 is extended by N-H O hydrogen bonds and π π stacking interactions. Furthermore, the antioxidant activity of 1 was evaluated. The scavenging activity of 1 to DPPH free radical is better than that of the parent compound chrysin.
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Jiegou Huaxue
ISSN: 0254-5861
Year: 2009
Issue: 9
Volume: 28
Page: 1112-1120
0 . 5 4 4
JCR@2009
0 . 8 9 3
JCR@2020
ESI Discipline: CHEMISTRY;
JCR Journal Grade:4
CAS Journal Grade:4
Cited Count:
WoS CC Cited Count: 1
SCOPUS Cited Count:
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 6