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.

摘要

本研究应用2-(4-甲氧基苯氧基)丙酸(HPMP)制备其烷基化和酯化衍生物，并考察其相应的甜味抑制作用。这些取代衍生物的结构通过 NMR 和 IR 表征，以确保它们的个体修饰。利用电子舌预测衍生物的甜味抑制作用，建立甜味预测模型根据甜味剂类型、甜味剂和衍生物浓度进行三维测量。此外，还研究了甜味抑制与其他味道特性的相互作用。目前的结果表明，对于烷基化衍生物，甲基化衍生物的甜度抑制率高于乙基和丙基衍生物，对位取代衍生物的甜度抑制率大于邻位和间位-职位。有趣的是，这项研究表明酯化作用导致轻微的甜味抑制作用。基于目前的结果，提出 HPMP 分子上疏水和亲水基团的比例通过与甜味受体活性位点的结合能力在调节其相应的甜味抑制中起关键作用。