二氢猕猴桃内酯的合成及作为卷烟香料的应用  

Synthesis and application of dihydroactinidiolide 1 as tobacco flavorant

作　　者：陈永宽[1] 孔宁川[1] 杨伟祖[1] 李聪[2] 

机构地区：[1]云南烟草科学研究院从事烟用香原料合成与应用的研究,昆明650106 [2]云南大学化学系,昆明650091

出　　处：《中国烟草学报》2003年第2期10-12,共3页Acta Tabacaria Sinica

基　　金：国家烟草专卖局资助项目 (合同号 981 0 1 9)

摘　　要：经过三步反应即环化反应、Darzen反应和氧化反应 ,柠檬醛 4转化成重要的挥发性香料组分二氢猕猴桃内酯 1(9-氧杂 - 1,5 ,5 -三甲基 -双环 [4,3,0 ]壬 - 6 -烯 - 8-酮 ) ,总产率为 33.5 %。该合成方法的关键步骤是 ,β-环柠檬醛 3与溴乙酸乙酯经过 Darzen反应生成β-环高柠檬醛 2。合成得到的二氢猕猴桃内酯 1经 mp、IR、MS、1 HNMR和元素分析鉴定。结果表明 ,化合物 1应用于烤烟型卷烟香料中具有增加卷烟香气 ,丰满卷烟香味和降低刺激的作用。Chtral4 has been converted through a three-step cyclic reaction, reaction i.e. Darzen reaction and oxidation reaction, into the important volatile flavor and armoa component of dihydroactinidiolide 1 (9-oxa-1,5,5-trimethy-bicyclo non-6-en-8-one) in 33.5 overall yiled. The key step involves the formation of β-homocyclocitral 2 by Darzen reaction of β-cyclocitral 3 with ethyl bromo acetate. Te title compound 1 was identified by mp, IR, MS, +1HNMR and elemental analysis, and the compound 1 was used in virginia type cigarettes as flavorant. The experimental cigarettes were found to have more tobacco smoke flavor, smoother body sensation and less harshness.

关 键 词：卷烟 二氢猕猴桃内酯 合成 香料 

分 类 号：TS42[农业科学—烟草工业]