3-[4-(Bromomethyl)phenyl]-7-(diethylamino)-2H-1-benzopyran-2-one (MPAC-Br): A highly sensitive fluorescent derivatization reagent for carboxylic acids in high-performance liquid chromatography

Article abstract of DOI:10.1248/cpb.44.793

7-Dimethylaminocoumarin derivatives were synthesized and the characteristics of their absorption and emission spectra were investigated. Among them, 3-aryl-7-dimethylaminocoumarins were shown to be promising candidates as the fluorogenic groups for highly sensitive derivatization reagents. Based on the spectroscopic studies, 3-[4-(bromomethyl)phenyl]-7-(diethylamino)-2H-1-benzopyran-2-one (MPAC-Br) was designed and synthesized as a fluorescent derivatization reagent for carboxylic acids in HPLC. Saturated carboxylic acids (C₄-C₁₈) were derivatized almost quantitatively into the corresponding fluorescent MPAC-esters by treatment with MPAC-Br. The MPAC-esters of these acids were clearly separated on a reversed-phase HPLC column (Inertsil ODS-2, mobile phase: methanol-water, excitation wavelength 403 nm; emission wavelength 474 nm). The detection limit (S/N=17) of lauric acid, as a test compound, was 15fmol/10μl.

Full text of DOI:10.1248/cpb.44.793

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