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

摘要:

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1.4 μg/mL。

Abstract:

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-chloro-1-ethanol. The optimum reaction conditions were as follows: n(3-methyl-4-oxooctanoic acid):n(2-chloro-1-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.