凉味剂薄荷基甲酸乙二醇酯的合成

Synthesis of Cooling Agent 2-hydroxyethyl P-menthane-3-carboxylate

为合成得到新型凉味剂薄荷甲酸乙二醇酯,并对其凉感进行感官评价。以薄荷基甲酸和氯乙醇为原料,用薄荷基甲酸与Na2CO3成盐,吡啶为溶剂和相催化剂,亲和取代反应制得薄荷基甲酸乙二醇酯,确定优化条件为:n(薄荷基甲酸):n(氯乙醇)=1:1.5,n(薄荷甲酸):n(碳酸钠)=1:1,n(薄荷甲酸):n(吡啶)=1:17,反应温度为100℃,反应时间4 h,收率达86.41%。目标化合物经过IR,1HNMR及MS对其结构进行了鉴定。薄荷基甲酸乙二醇酯具有较好生理凉感,味觉凉感阈值为1.4μg/mL。

In this research, 2-hydroxyethyl p-menthane-3-carboxylate was synthesized and its sensory quality was evaluated. Sodium carboxylate were obtained by reaction of menthyl formic acid and Na2CO3. Then using pyridine as reaction medium, 2-hydroxyethyl p-menthane-3-carboxylate was synthesized by nucleophilic substitution reaction of menthyl formic acid and 2-ehloro-1-ethanol. The optimum reaction conditions were as follows： n（3-methyl-4-oxooctanoic acid）：n（2-chloro-l-ethanol） 1：1.5, n（3-methyl-4-oxooctanoic acid）：n（Na2CO3） 1：1, n（3-methyl-4- oxooctanoic acid） ： n（pyridine） 1：17, reaction time 4 h and reaction temperature 100 ℃, under which the total product yield was 86.41%. The structure of theproduct was characterized by IR, 1HNMR and MS. Sensory evaluation showed that its cooling threshold value was 1.4 μg/mL.