Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins

The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C18(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.