Influence of alkylation and esterification of 2-(4-methoxyphenoxy) propionic acid on sweet inhibition property and its manipulating mechanism

Abstract

ABSTRACT The current study applied 2-(4-methoxyphenoxy) propionic acid (HPMP) to prepare its alkylated and esterified derivatives and then investigated their corresponding sweetness inhibitory effect. The structure of these substituted derivatives were characterized by NMR and IR for ensuring their individual modification. The electronic tongue was used to predict the sweetness inhibitory effect of the derivatives, and a sweet prediction model was established via a three-dimensional measurement in term of sweetener type, sweetener and derivative concentrations. Furthermore, the interaction of sweetness inhibition with other taste properties was also studied. The current results indicated that, for alkylated derivatives, the sweetness inhibition rate of methyl-modified derivatives was higher than that of ethyl and propyl derivatives, and the inhibition rate of para-substituted derivatives was greater than that of ortho- and meta-positions. Interestingly, this study revealed that the esterification led to a minor sweetness inhibitory effect. Based on the current results, it is proposed that the ratio of hydrophobic and hydrophilic groups on the HPMP molecules plays the key role in regulating their corresponding sweetness inhibition via a binding capacity with the active site of sweet taste receptors.