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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.

Citation

Bruno Dacunha-Marinho, Ana Martínez, Ramón J Estévez. 7-hydroxy-5-methoxy-6,8-dimethylflavanone: a natural flavonoid. Acta crystallographica. Section C, Crystal structure communications. 2008 Jun;64(Pt 6):o353-6

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PMID: 18535347

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