中国烟草学报2024，Vol.30Issue(4)：1-9,9.DOI:10.16472/j.chinatobacco.2023.123
百里香酚-β-D-葡萄糖苷的合成及转移率研究
Synthesis and transfer rate of thymol-β-D-glucopyranoside
摘要
Abstract
[Background]This study aim to improve the thermal stability of thymol by conducting glycosylation research.[Methods]Acetyl bromide-α-D-glucose(Ⅰ)and thymol(Ⅱ)were reacted under ionic liquid catalysis to synthesize thymol-2,3,4,6-tetra-O-acetyl-β-D-glucoside(Ⅲ),and compound Ⅲ was deacetylated to obtain thymol-β-D-glucoside(Ⅳ).The thermal stability of compound Ⅳ was investigated through TG-DTG,its pyrolysis behavior was studied through Py-GC-MS,and the pyrolytic transfer rate of compounds Ⅱ and Ⅳ in the particulate phase of mainstream smoke,as well as the change in transfer rate over time,was researched through GC-MS.[Results]The reaction conditions for the catalytic synthesis of compound Ⅲ using ionic liquids were as follows:sodium hydroxide aqueous solution as acid binding agent,1-butyl-3-methyl-bromimidazolium as catalyst,dichloromethane as solvent,n(Ⅰ):n(NaOH)=1:2,n(Ⅰ):n(1-butyl-3-methyl-bromimidazolium)=1:1,n(Ⅰ):n(Ⅱ)=1:1,reaction time 4 hours,with a yield of 55.1％for compound Ⅲ.Under the action of sodium methoxide,compound Ⅲ was deacetylated to obtain the target glucoside Ⅳ,with a yield of 80.6％.The structure of the product was confirmed by 1HNMR,13CNMR,IR,and HRMS.The thermal stability of compound Ⅳ was superior to that of compound Ⅱ,and the main pyrolysis products of compound Ⅳ at different temperatures were compound Ⅱ,indicating that the fragrance stability of compound Ⅳ was superior to that of compound Ⅱ.[Conclusion]Thymol-β-D-glucoside can improve the drawbacks of thymol and can be used as a thermally stable and fragrance-stable precursor for tobacco flavoring.关键词
糖苷/百里香酚-β-D-葡萄糖苷/热稳定性/热裂解/转移率Key words
glycosides/thymol-β-D-glucoside/thermal stability/pyrolysis/transfer rate引用本文复制引用
张改红,石栋栋,杜帅,许航,夏金华,白冰,毛多斌..百里香酚-β-D-葡萄糖苷的合成及转移率研究[J].中国烟草学报,2024,30(4):1-9,9.基金项目
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)) （110202201053(SJ-03）
