香芹酚-β-D-葡萄糖苷的合成及在卷烟中的应用

Synthesis of carvacrol-β-D-glucoside and its use in cigarette flavoring

为了开发释香稳定型烟用香料,采用相转移催化法合成香芹酚-β-D-葡萄糖苷,对合成的香芹酚-β-D-葡萄糖苷进行热裂解分析,并将其加入卷烟中,考察其向主流烟气粒相中的热解释放行为及加香应用效果。结果表明:(1)采用相转移催化法可制得香芹酚-β-D-葡萄糖苷,产物结构通过1H NMR、13C NMR、FTIR和HRMS技术得到确证。(2)在不同温度下,香芹酚-β-D-葡萄糖苷的主要裂解产物均为香芹酚。(3)以不同加香方式在卷烟中添加香芹酚-β-D-葡萄糖苷可以达到不同的加香效果。烟丝加香方式下添加香芹酚-β-D-葡萄糖苷的卷烟释香更均匀稳定,加香效果优于香芹酚。(4)添加香芹酚-β-D-葡萄糖苷的卷烟在抽吸时可向主流烟气粒相中释放香芹酚,且随着加香量的增大香芹酚释放量呈增大趋势,而在主流烟气粒相中香芹酚的转移率则较稳定。

In order to develop tobacco flavors with good aroma release stability,a phase transfer catalytic method was used to synthesize carvacrol-β-D-glucoside.The pyrolysis of the synthesized carvacrol-β-D-glucoside was analyzed.It was also added to cigarettes to investigate its pyrolysis release behavior in the particulate phase of mainstream cigarette smoke and its application effect on flavoring.The results showed that:1)Carvacrol-β-D-glucoside could be obtained by the phase transfer catalytic method,and its structure was confirmed by 1H NMR,13C NMR,FTIR,and HRMS.2)At different heating temperatures,the main cleavage product of carvacrol-β-D-glucoside was carvacrol.3)By adding carvacrol-β-D-glucoside to cigarettes in different flavoring ways,different flavoring effects could be achieved.The aroma release of cigarettes with carvacrol-β-D-glucoside in cut tobacco was more uniform and stable,and the flavoring effect was better than that of cigarettes with adding carvacrol directly.4)Cigarettes with added carvacrol-β-D-glucoside could release carvacrol to the particulate phase of mainstream smoke during smoking,and the release of carvacrol increased with the increase of flavoring amount,while the transfer rate of carvacrol to the particulate phase of mainstream smoke was relatively stable.