新型草莓酰基呋喃木糖合成及其卷烟加香效应

Synthesis of 1,2-O-propylidene-3-O-(2-methyl-2-penetenacyl)-5-O-benzoyl-D-xylofuranose and Its Flavoring in Cigarette

以木糖、苯甲酰氯和2-甲基2-戊烯酸(草莓酸)为原料,以二环己基碳二亚胺(DCC)为缩合剂,在4-二甲氨基吡啶(4-DMAP)催化作用下,合成了化合物1,2-O-异丙叉基-3-O-(2-甲基-2-戊烯酰基)-5-O-苯甲酰基呋喃木糖,其结构经IR、1HNMR、HRMS图谱比对得到验证,并对其进行了热裂解和卷烟加香试验。结果表明,(1)合成产物为目标产物,且操作简单,收率高;(2)温度对合成产物的热裂解产物种类和含量有较大影响,随着裂解温度的升高,裂解程度越来越剧烈。但各温度段主要产物有呋喃、月桂烯、2-甲基2-戊烯酸等香味物质;(3)合成产物的用量为0.004%～0.008%时,与烟香谐调,可以改善卷烟香气质,增加香气量,降低刺激性和杂气,改善余味。同时,不同产地的烟丝对该种香原料的最佳添加量要求稍有不同。

The compound 1,2-O-propylidene-3-O-（2-methyl-2-penetenacyl）-5-O-benzoyl-D-xylofuranose was synthesized from xylose,benzoyl chloride and 2-methyl-2-pentenoicacid with 4-DMAP as catalyst and DCC as dehydration reagent.Its structure was confirmed by IR,1H NMR,HRMS spectra.The pyrolysis of the precursor and the application of the compound in blended cigarette flavoring were studied as well.The results show that：（1） The target compound can be synthetized in simpler operation and with higher yield.（2） Temperature has a great influence on the types and contents of pyrolysis of the compound;with the rise of pyrolytic temperature the cracking degree becomes more and more severe.The contents of furan,myrcene,2-methyl-2-pentenoicacid and so on are higher in each temperature section.（3） When the dosage of the synthesized compound falls in the range of 0.004%～0.008%,the compound is in harmony with tobacco,and can improve aroma quality,enhance aroma quantity,reduce irritancy and improve aftertaste of cigarette smoke.Meanwhile a slight difference shows between tobacco from different areas in the requirement of the optimum additive amount of this compound.