7-hydroxy-5-methoxy-6,8-dimethylflavanone: a natural flavonoid.
The title flavonoid [systematic name: (2S)-7-hydroxy-5-methoxy-6,8-dimethyl-2-phenyl-3,4-dihydrochromen-4(2H)-one], C18H18O4, displays statistical conformational disorder, with three conformations of the molecule involving three orientations of the phenyl ring and two orientations of the fused heterocyclic ring. The conformational disorder is correlated with the isomerization equilibrium between the flavanone and chalcone forms. The conformational behaviour has a potential impact on the biological activity of this class of compounds. Moreover, pi stacking interactions at van der Waals distances are present between the aromatic rings of chroman-4-one groups of symmetry-related molecules. Apart from these pi-pi interactions, molecules are linked by strong O-H...O hydrogen bonds between hydroxy and carbonyl groups.
Edifico CACTUS, Campus sur Unidade de Raios X, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain. raiosxp@usc.es
Bruno
B
Dacunha-Marinho
Ana
A
Martínez
Ramón J
RJ
Estévez
D004583:Electrons; D044950:Flavanones / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation
C530120:7-hydroxy-5-methoxy-6,8-dimethylflavanone; D044950:Flavanones; D005419:Flavonoids; C028610:flavanone