1-O-[3-(2-呋喃基)丙烯酰基]-β-D-吡喃果糖的合成及应用

Synthesis and Application of 1-O-[3-(2-Furanyl)acryloyl]-β-D-fructopyranose

为开发新型卷烟保润剂,以D-果糖和糠醛为起始原料,设计合成了一种新化合物1-O-[3-(2-呋喃基)丙烯酰基]-β-D-吡喃果糖(VIII),用IR,1H NMR,13C NMR,ESI-MS和元素分析表征了VIII的结构,并进行了添加于烟丝后的物理保润性能测试、热裂解分析、卷烟烟气安全性生物学评价和感官质量评价。结果显示:1所合成的化合物为目标产物;2VIII在干燥条件下的物理保润性能优于丙二醇;3VIII热裂解时会释放出呋喃类香味成分;4添加VIII的试验卷烟和空白卷烟的烟气生物学效应相当;5VIII可降低卷烟烟气干燥感和刺激性,提高烟气香气量及改善余味。

In order to develop novel cigarette humectants, a new compound, Ⅷ, was designed and synthesized with D-fructose and furfural as starting materials. The structure of the product was characterized by IR, 1H NMR, 13C NMR, ESI-MS and elemental analysis. The moisture retentivity test, pyrolysis analysis, biological effects assessment of tobacco smoke were conducted after the product being applied to cigarette, and the sensory quality of cigarette was also evaluated. The results showed that： 1） The obtained product was proved to be the target compound 1-O-[3-（2-furanyl）acryloyl]-β-D-fructopyranose. 2） The moisture retentivity of Ⅷ was better than that of propylene glycol in dry environments. 3） Ⅷreleased aromatic furan constituents during pyrolysis. 4） The cigarettes added with Ⅷ were comparable to blank cigarettes in the biological effects of smoke. 5） Ⅷ reduced the dryness and irritation, increased the aroma, and improved the aftertaste of cigarette smoke.