α,β-不饱和γ-内酯的合成及香气特征研究  

Syntheses and odor features of α,β-unsaturated γ-lactones

作　　者：邵军强[1] 戴怡凤[1] 刘永国[1] 孙宝国[1] 陈海涛[1] 田红玉[1] 

机构地区：[1]北京工商大学食品学院北京市食品风味化学重点实验室,北京100048

出　　处：《日用化学工业》2013年第4期294-298,302,共6页China Surfactant Detergent & Cosmetics

基　　金：国家自然科学基金资助项目(No.31271932和31071610);国家科技部科技支撑计划资助项目(2011BAD23B01);北京市教委科技计划重点资助项目(KZ201110011015)

摘　　要：以脂肪醛和丙二酸为起始原料,通过Knoevenagel缩合反应制得(E)-3-链烯酸,产率为58%～85%;(E)-3-链烯酸用双氧水和甲酸氧化后在碱性条件下关环得到3-羟基-γ-内酯,产率为80%～88%;3-羟基-γ-内酯与甲磺酰氯反应,得到3-甲磺酰氧基-γ-内酯,然后在三乙胺的作用下发生消除反应得到α,β-不饱和γ-内酯,产率为87%～90%。所有产物的结构都通过1HNMR和13CNMR进行了确认。该系列的化合物均呈现令人愉悦的甜香、奶香和水果香味,与相应的饱和γ-内酯相比有明显区别。A series of （E） -β - alkenoic acid was prepared via the Knoevenagel reaction of aliphatic aldehydes and malonic acid with yield of 58% - 85%. The （E） - β- alkenoie acids were oxidized by H202 and formic acid followed by ring closure in the presence of alkali and 3 - hydroxy - Y - lactones was formed with yield of 80% - 88%. The 3 - hydroxy - y - lactones were further reacted with methylsulfonyl chloride to produce 3 -methylsulfoxy -T -laetones and followed by elimination reaction with triethylamine to produce a,β-unsaturated Y - lactones with yield of 87% - 90%. The structures of all of the products were characterized by HNMR and J3CNMR. The odor features of the prepared a,β- unsaturated Y -lactones were assessed. They present pleasant sweet, milk -like and fruity aroma,which are different from that of corresponding saturated y - lactones.

关 键 词：香料 α β-不饱和γ-内酯 合成 香气特征 

分 类 号：TQ655[化学工程—精细化工]