糠醇-β-D-葡萄糖苷的合成、热裂解及卷烟主流烟气中糠醇的转移率  

Synthesis and pyrolysis of furfuryl alcohol-β-D-glucoside and transfer rate of furfuryl alcohol to mainstream cigarette smoke

作　　者：张改红 杜帅 许航 石栋栋 尚紫博 薛晶晶 王梦瑶 许志杰 毛多斌 ZHANG Gaihong;DU Shuai;XU Hang;SHI Dongdong;SHANG Zibo;XUE Jingjing;WANG Mengyao;XU Zhijie;MAO Duobin(College of Tobacco Science and Engineering,Zhengzhou University of Light Industry,Zhengzhou 450001,China;Bell Flavors&Fragrances(Shanghai)Co.,Ltd.,Shanghai 201600,China)

机构地区：[1]郑州轻工业大学烟草科学与工程学院,郑州450001 [2]贝尔香精香料(上海)有限公司,上海市201600

出　　处：《烟草科技》2024年第7期1-7,共7页Tobacco Science & Technology

基　　金：中国烟草总公司重大科技项目“香味前体物液相色谱-质谱数据库构建及应用研究”[110202201053(SJ-03)];河南省科技攻关计划项目“焦甜香香料前体的合成及加香应用”(192102110212)。

摘　　要：为了提高糠醇-β-D-葡萄糖苷的合成产率,对其合成条件进行了优化,并对糠醇-β-D-葡萄糖苷的热裂解产物及卷烟主流烟气粒相中糠醇的转移率进行了分析。结果表明:①糠醇与乙酰溴-α-D-葡萄糖在以硅胶担载的Ag_(2)CO_(3)为催化剂、NaOH固体为缚酸剂的条件下进行糖苷化反应,得到糠醇-2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷,产率为45.9%;糠醇-2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷脱去乙酰基,得到糠醇-β-D-葡萄糖苷,产率为90.1%。合成产物的结构通过1HNMR、13CNMR、FTIR和HRMS技术得到确证。②在不同温度下,糠醇-β-D-葡萄糖苷的主要裂解产物均为糠醇。③糠醇-β-D-葡萄糖苷在卷烟燃吸时能够释放出糠醇,主流烟气粒相中糠醇的转移率为0.68%。To improve the synthesis yield of furfuryl alcohol-β-D-glucoside in smoke,synthesis conditions and pyrolysis products were investigated and the transfer rate of furfuryl alcohol to the particulate phase of mainstream cigarette smoke was measured.The results showed that:1)Furfuryl alcohol and acetyl bromide-α-D-glucose underwent glycosylation reaction under the catalysis of Ag_(2)CO_(3)supported on silica gel and NaOH solid as acid binder to obtain furfuryl alcohol-2,3,4,6-tetra-O-acetyl-β-D-glucoside.The optimized yield of furfuryl alcohol-2,3,4,6-tetra-O-acetyl-β-D-glucoside was 45.9%.The intermediate furfuryl alcohol-2,3,4,6-tetra-O-acetyl-β-D-glucoside was deacetylated to obtain furfuryl alcohol-β-D-glucoside with a yield of 90.1%.The structures of the intermediates and the final products were confirmed by 1H NMR,13C NMR,FTIR and HRMS.2)At different temperatures,the main cleavage product of furfuryl alcohol-β-D-glucoside was furfuryl alcohol.3)Furfuryl alcohol-β-D-glucoside released furfuryl alcohol during cigarette smoking,and the transfer rate of furfuryl alcohol to the particulate phase of mainstream cigarette smoke was 0.68%.

关 键 词：卷烟 糠醇-β-D-葡萄糖苷 糖苷化 转移率 热裂解 

分 类 号：TS411.2[农业科学—烟草工业] O621.3[理学—有机化学]