4-甲基愈创木酚-β-D-葡萄糖苷的合成及其在卷烟加香中的应用研究  

Synthesis of 4-methylguaiacol-β-D-glucoside and its application in cigarettes flavoring

作　　者：张改红 杜帅 许航 徐月莹 石栋栋 毛多斌 ZHANG Gaihong;DU Shuai;XU Hang;XU Yueying;SHI Dongdong;MAO Duobin(College of Tobacco Science and Engineering,Zhengzhou University of Light Industry,Zhengzhou,Henan 450001,China)

机构地区：[1]郑州轻工业大学烟草科学与工程学院,河南郑州450001

出　　处：《湖南农业大学学报(自然科学版)》2025年第2期16-23,共8页Journal of Hunan Agricultural University(Natural Sciences)

基　　金：中国烟草总公司重大科技项目(110202201053(SJ–03));河南省科技攻关计划项目(192102110212);郑州轻工业大学校基础研究基金项目(23XJCYJ032)。

摘　　要：为了开发热稳定及释香稳定型烟用香料,采用离子液体催化法合成4-甲基愈创木酚-β-D-葡萄糖苷,对合成的4-甲基愈创木酚-β-D-葡萄糖苷进行热稳定及热裂解分析,并考察其加入卷烟后向主流烟气粒相中释放4-甲基愈创木酚的情况。结果表明:以1-丁基-3-甲基-溴化咪唑鎓为离子液体催化剂,合成了4-甲基愈创木酚-2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷,收率为49.3%;脱去乙酰基,得到4-甲基愈创木酚-β-D-葡萄糖苷,收率为87.3%;热重-微商热重(TG-DTG)分析表明4-甲基愈创木酚-β-D-葡萄糖苷的热稳定性优于4-甲基愈创木酚;热裂解-气相色谱-质谱(Py-GC-MS)分析表明4-甲基愈创木酚-β-D-葡萄糖苷在300、600、900℃的主要裂解产物均为4-甲基愈创木酚;烟丝加香方式和卷烟纸加香方式下烟气中4-甲基愈创木酚的释放量不同,加香效果不同;添加4-甲基愈创木酚-β-D-葡萄糖苷的加香卷烟燃吸时能释放4-甲基愈创木酚,并且释香更均匀、逐口稳定性更好,效果优于添加4-甲基愈创木酚的;推测4-甲基愈创木酚-β-D-葡萄糖苷可能是一种释香稳定的香料前体。In order to develop thermal and aroma stable tobacco flavorings,4-methylguaiacol-β-D-glucoside was synthesized using ionic liquid catalytic method,the synthesized 4-methylguaiacol-β-D-glucoside was subjected to thermal stability and pyrolysis analysis,and added to cigarettes to investigate the release of 4-methylguaiacol into mainstream smoke particles.The results showed that 1-Butyl-3-methyl-imidazonium bromide was selected as an ionic liquid catalyst to synthesize 4-methylguaiacol-2,3,4,6-tetra-O-acetyl-β-D-glucoside with a yield of 49.3%.The target 4-methylguaiacol-β-D-glucoside was obtained by deacetylation of 4-methylguaiacol-2,3,4,6-tetra-O-acetyl-β-D-glucoside with a yield of 87.3%.The thermal stability of 4-methylguaiacol-β-D-glucoside was found to be superior to that of 4-methylguaiacol using the thermogravimetric analysis(TG-DTG).Through pyrolysis gas chromatography-mass spectrometry(Py-GC-MS)technology,it was shown that the main cracking product of 4-methylguaiacol-β-D-glucoside at 300,600 and 900℃was 4-methylguaiacol.The release amount of 4-methylguaiacol in smoke is different between the tobacco flavoring method and the cigarette paper flavoring method,resulting in different flavoring effects.Flavored cigarettes added with 4-methylguaiacol-β-D-glucoside can release 4-methylguaiacol during smoking,and the release of fragrance is more uniform,with better stability per bite,and the effect is better compared to 4-methylguaiacol addition.We speculate that 4-methylguaiacol-β-D-glucoside can be a stable fragrance precursor.

关 键 词：卷烟 4-甲基愈创木酚-β-D-葡萄糖苷 糖苷化 离子液体 加香 

分 类 号：O629.13[理学—有机化学] TS411[理学—化学]