Characterization and Structural Analysis of Genkwanin, a Natural Product from Callicarpa americana

The natural compound Genkwanin (systematic name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one) C16H12O5 (1) is a non-glycosylated flavonoid isolated from Callicarpa americana. Microcrystals of Genkwanin were prepared by slow evaporation of a methanol solution under low temperature conditions. The structure of 1 was determined based on spectroscopic analyses, one-dimensional NMR, HRESIMS and was confirmed by single-crystal X-ray diffraction. The crystals grow as very thin needles with an extremely high aspect ratio and with the long axis (along the y-axis) corresponding to the very short unit cell b-axis. There are two independent molecules in the asymmetric unit with two different conformations and modes of packing in the crystal. One molecule has a higher degree on non-planarity than the other. The short stacking distance and separation between the molecules implies a high degree of co-planarity consistent with a conjugated system. The crystal structure is non-centrosymmetric but achiral.