Kinetic Modeling of Malonylgenistin and Malonyldaidzin Conversions under Alkaline Conditions and Elevated Temperatures

Abstract

The conversion and degradation of malonylglucosides were kinetically characterized under elevated pH/heat conditions. Malonylgenistin and malonyldaidzin were heated at 60, 80, and 100 °C and pH values of 8.5, 9, and 9.5. A simple kinetic model was developed, which adequately predicted the conversion and degradation reactions. The conversion and degradation rates increased as temperature and pH increased. The rates of conversion of both malonylglucosides into their respective β-glucosides were comparable under all pH/heat treatments. However, at 100 °C, the rates of degradation of malonyldaidzin were approximately double those of malonylgenistin, under all pH treatments. When malonlydaidzin was heated at 100 °C and pH 9.5, degradation of the produced daidzin occurred. Therefore, an alternative kinetic model was developed to better predict the conversion and degradation of malonyldaidzin occurring at 100 °C and pH 9.5. The models developed provide soy food manufacturers with guidelines for better control of the profile and level of isoflavones. Keywords: Isoflavones; β-glucosides; malonylglucosides; kinetics; isoflavone conversions and degradations