2-(4-甲氧基苯氧基)丙酸卤代衍生物的合成及其甜味抑制作用评价  

Synthesis and Sweetness Inhibitory Effect of 2-(4-Methoxyphenoxy)Propionic Acid Halogenated Derivatives

作　　者：胡涵翠 李加兴 郑建仙[1] HU Hancui;LI Jiaxing;ZHENG Jianxian(School of Food Science and Engineering,South China University of Technology,Guangzhou 510640,China;Hunan Provincial Research Centre of Well and Rock Salt Engineering Technology,Changsha 410004,China)

机构地区：[1]华南理工大学食品科学与工程学院,广东广州510640 [2]湖南省井矿盐工程技术研究中心,湖南长沙410004

出　　处：《食品科学》2022年第22期17-23,共7页Food Science

基　　金：国家自然科学基金面上项目(31972010)。

摘　　要：为探究卤素取代对2-(4-甲氧基苯氧基)丙酸(2-(4-methoxyphenoxy)propionic acid,HPMP)甜味抑制特性的影响,通过对HPMP苯环的2位或3位进行卤素(F、Cl、Br)取代,合成6种HPMP卤代衍生物并进行结构表征,采用电子舌评价其甜味抑制作用。结果表明:HPMP卤代衍生物可竞争性抑制甜味,在苯环的2位上引入卤原子的衍生物均存在明显的量效关系;6种衍生物对蔗糖、果糖、葡萄糖、木糖醇和赤藓糖醇均能表现出一定的甜味抑制作用;氟代、氯代衍生物的甜味抑制活性较强,推测卤素取代基的尺寸及电负性大小可能是造成甜味抑制效果差异的关键因素。本研究表明卤素取代对HPMP发挥甜味抑制作用具有重要意义,从而为甜味抑制化合物的构效关系研究提供可靠的理论基础。To explore the effect of halogen substitution on the sweetness inhibition properties of 2-(4-methoxyphenoxy)propionic acid(HPMP),six halogenated derivatives of HPMP were synthesized through halogen(F,Cl or Br)substitution at the 2-or 3-position of the benzene ring of HPMP and characterized structurally,and their sweetness inhibition properties were evaluated by electronic tongue.The results showed that the six halogenated derivatives could competitively inhibit sweetness.In addition,a significant dose-effect relationship was observed for the derivatives with halogen atoms introduced at the 2-position of the benzene ring.All six derivatives exhibited inhibitory effects on sucrose,fructose,glucose,xylitol and erythritol.Furthermore,the fluorinated and chlorinated derivatives showed stronger inhibitory effect on the sweetness of the aforementioned sweeteners.Therefore,it was speculated that the size and electronegativity of halogen substituents may be the key factors causing different sweetness inhibitory activity.This study indicates the importance of halogen substitution in the sweetness inhibition effect of HPMP,and provide a reliable theoretical basis for the study of the structure-activity relationship of sweetness-inhibiting compounds.

关 键 词：2-(4-甲氧基苯氧基)丙酸 卤素取代 甜味抑制 电子舌 

分 类 号：TS202.3[轻工技术与工程—食品科学]