凉味剂N-乙基-L-薄荷基甲酰胺的合成  

Synthesis of Cooling Agent N-Ethyl-L-menthane-3-carboxamide

作　　者：田红玉[1] 丁瑞[1] 孙宝国[1] 欧阳天惠[1] 励建荣 韩晓祥 

机构地区：[1]北京工商大学化学与环境工程学院,北京100037 [2]浙江工商大学食品生物与环境工程学院,浙江杭州310035

出　　处：《精细化工》2008年第11期1097-1100,1113,共5页Fine Chemicals

基　　金：浙江省“食品科学与工程”重中之重学科建设项目开放课题(ZSZKF200714);北京市新世纪百千万人才工程培养经费资助项目~~

摘　　要：凉味剂N-乙基-L-薄荷基甲酰胺,凉感强度是薄荷醇的1.5倍,具有无气息、低挥发性、无苦味、无灼烧感、低毒性、凉感持久等优点。该文考察了以薄荷醇为起始原料,通过格氏反应制备N-乙基-L-薄荷基甲酰胺的方法。薄荷醇与五氯化磷在无水氯化铁的催化作用下反应得到氯代物,收率可达90%左右。薄荷基氯的格氏试剂与二氧化碳反应,干冰与二氧化碳气体相比较,二氧化碳气体反应得到薄荷基-3-羧酸的产率更高,格氏试剂与二氧化碳气体的摩尔比为1∶45,反应温度为-40℃,得到薄荷基3-羧酸的产率达55%。薄荷基-3-羧酸转化为酰氯后与乙胺反应得粗产物,GC分析表明,其中薄荷酰胺和新薄荷酰胺的摩尔比为87/13。粗产物经重结晶后得纯的N-乙基-L-薄荷基甲酰胺。总收率约40%。The new cooling agent N-ethyl-L-menthane-3-carboxamide （ Ⅰ ） has cooling intensity 1.5 folds as strong as L-menthol. It possesses many advantages, such as weak odor, low volatility, no bitter taste,no burning sensation,low toxicity and long-lasting cooling sensation. Synthesis of Ⅰ started from L-menthol through the Grignard reaction. L-Menthol reacted with phosphorus pentachloride catalyzed by anhydrous ferric chloride to give the chlorinated product menthyl chloride （ Ⅱ ） in about 90% yield. Menthane-3-carboxylic acid（ Ⅲ ） was obtained in about 55% yield by reacting the Grignard reagent of Ⅱ with gaseous carbon dioxide at -40 ℃ with the Grignard reagent/carbon dioxide molar ratio of 1/ 45. Then Ⅲ was transformed to acid chloride, and reacted with ethyl amine to give the crude product, in which the menthane-3-carboxamide/neomenthane-3-carboxamide ratio was 87/13 by GC analysis. Reerystallization of the crude product gave pure Ⅰ. The overall yield was about 40%.

关 键 词：凉味剂 L-薄荷醇 N-乙基-L-薄荷基甲酰胺 格氏反应 香料与香精 

分 类 号：TQ651.1[化学工程—精细化工]