Evaluating the enantioselective capability of a cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase towards 5,7,2'‐trihydroxyflavanone

Abstract

In this study, an evaluation of the enantioselective of a chiral flavanone with 2'‐OH substitution (5,7,2'‐trihydroxyflavanone) on ring C was studied by high performance liquid chromatography using the cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase with n‐hexane and iso‐propanol doped with 0.1% (v/v) trifluoroacetic acid as a mobile phase. Column temperature and mobile phase composition were investigated in the assessment of the chiral separation by considering the enantiomeric resolution factor (Rs). Also, the absolute configurations of single enantiomers were determined by measuring CD spectra based on the exciton‐coupling method. The results pointed out that the 2'‐hydroxy group was capable of advancing the enantioselective of flavanones on the cellulose tris(3,5‐dimethylphenyl carbamate)‐based stationary phase when the column temperature was higher than 30 oC and the mobile phase was of 10% iso‐propanol doped with 0.1% (v/v) TFA in n‐hexane. The absolute configuration determination showed that the enantiomer with the 2S configuration was the first eluted and, consequently, the elution order of the enantiomers of 5,7,2'‐trihydroxyflavanone at optimal conditions was in contrast to 5,7,4'‐trihydroxyflavanone and 5,7‐dihydroxyflavanone. The 2'‐OH substitution on the phenyl moiety appears to be capable of inducing or altering the strength of inter‐and intramolecular interactions when the chiral selectors are immobilized on the silica stationary phase.