Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones.
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'-hydroxychalcones in acidic solution. These monohydroxyflavanones were characterized using a gas chromatography-mass 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.
Kagawa
Hitoshi
H
Department of Organic Synthesis, School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Tokyo 108-8641, Japan. kagawah@pharm.kitasato-u.ac.jp
Shigematsu
Asako
A
Ohta
Shigeru
S
Harigaya
Yoshihiro
Y
D044950:Flavanones / Q000032:analysis / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D013678:Technology, Pharmaceutical / Q000379:methods*
D044950:Flavanones