Preparative Monohydroxyflavanone Syntheses and a Protocol for Gas Chromatography-Mass Spectrometry Analysis of Monohydroxyflavanones

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We describe a facile efficient, and preparative approach for monohydroxyflavanone syntheses. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2′-hydroxy-chalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatographymass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. Ours is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. We are also the first to develop a procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metabolism and oxidation studies.
公益社団法人日本薬学会の論文
2005-05-01