薄荷甲酰胺类化合物的合成及鉴定

Synthesis and Sensory Evaluation of New Cooling Agent Menthyl Formylamines Compounds

摘要:

为合成得到新型凉味剂薄荷甲酰胺类化合物，并对其凉感进行感官评价。首先利用L-薄荷醇和Lucas 试剂经过氯代反应制成薄荷基氯，薄荷基氯与镁反应生成格式试剂，再与CO2反应得到薄荷基甲酸，薄荷基甲酸与二氯亚砜经酰化反应制成薄荷基甲酰氯，最后分别与乙胺，甘氨酸乙酯的盐酸盐，叔丁基胺和对甲氧基苯胺经酰胺化反应得到四种薄荷甲酰胺类化合物N-乙基-对薄荷基-3-羧酰胺(a)，乙酸(N-乙基-对薄荷基-3-羧酰胺)乙酯(b)，N-叔丁基-对薄荷基-3-羧酰胺(c)和N-(4-甲氧基苯基)-对薄荷基-3-羧酰胺(d)。合成的目标化合物均经过IR、1HNMR及MS对其结构进行了鉴定。经感官评价，化合物a、b、c和d凉感阈值分别为0.3 μg/mL、0.2 μg/mL、0.1 μg/mL和0.4 μg/mL。

Abstract:

Menthyl chlorine was synthesized by chlorinated reaction of L-menthol and Lucas reagent, then reacted with magnesium. Menthane-3-carboxylic acid was synthesized by the Grignard reagent of Menthyl Chlorinum and CO2. And then menthyl carboxyly chloride was obtained by thionyl chloride. Finally, N-ethyl-menthyl-3- carboxamide(a), acetic acid(N-ethyl- menthyl -3-carboxamide) ethyl(b), N-tert- butyl-menthyl-3-carboxamide(c) and N-(4–methoxy-phenyl)-menthyl-3-carboxamide(d)were synthesized by ethylamine, glycine ethyl ester hydrochloride, tert-butyl amine and anisidine with menthyl carboxyly chloride respectively. All structure of target compounds was characterized by IR,1HNMR and MS. The corresponding threshold of 5a, 5b, 5c and 5d was 0.3 μg/mL, 0.2 μg/mL, 0.1 μg/mL and 0.4 μg/mL by sensory evaluation.