异丁香酚-β-D-葡萄糖苷的合成及热裂解转移率
Synthesis and pyrolysis transfer rate of isoeugenol-β-D-glucopyranoside
张改红 1徐月莹 1石栋栋 1杨鹏飞 1黄申 1毛多斌1
作者信息
- 1. 郑州轻工业大学 食品与生物工程学院,河南 郑州 450002
- 折叠
摘要
以乙酰溴-α-D-葡萄糖(Ⅰ)作为糖基供体与异丁香酚(Ⅱ)进行反应,通过相转移催化法和离子液体催化法合成了异丁香酚-2,3,4,6-四-O-乙酰基-β-D-葡萄糖苷(Ⅲ),然后在甲醇钠中脱乙酰化得到异丁香酚-β-D-葡萄糖苷(Ⅳ).将化合物Ⅳ加入卷烟中,测试了其在卷烟主流烟气粒相中的转移率.结果表明,合成Ⅲ采用离子液体催化法(收率 56.8%)优于相转移催化法(收率 43.5%).离子液体催化法反应条件为:1-丁基-3-甲基-溴化咪唑 为催化剂、氯仿为溶剂、氢氧化钠水溶液为缚酸剂、n(Ⅰ)∶n(Ⅱ)= 0.8∶1,n(Ⅰ)∶n(1-丁基-3-甲基-溴化咪唑)= 1∶1、室温、反应时间 8 h.在上述条件下,化合物Ⅲ的收率为 56.8%.化合物Ⅲ在甲醇钠/甲醇溶液中反应脱去四乙酰基,得到化合物Ⅳ,收率 87.6%.卷烟燃吸过程中,化合物Ⅳ热裂解为异丁香酚,异丁香酚向主流烟气粒相中的转移率为 3.2%.
Abstract
Isoeugenol-2,3,4,6-tetra-O-acetyl-β-D-glucoside(Ⅲ)were synthesized from acetylbromide-α-D-glucose(Ⅰ)and isoeugenol(Ⅱ)through phase transfer catalysis and ionic liquid catalysis.Compound(Ⅲ)deacetylated in sodium methoxide to obtain isoeugenol-β-D-glucoside(Ⅳ).CompoundⅣ was added into cigarette and its transfer rate in the particle phase of cigarette mainstream smoke was analyzed.The results showed that the ionic liquid catalysis method(yield 56.8%)was superior to the phase transfer catalysis method(yield 43.5%).The reaction conditions of the ionic liquid catalytic method were as follows:1-butyl-3-methylimidazolium bromide as catalyst,chloroform as solvent,sodium hydroxide aqueous solution as acid binding agent,n(Ⅰ)∶n(Ⅱ)= 0.8∶1,n(Ⅰ)∶n(1-butyl-3-methylimidazolium bromide)= 1∶1,room temperature,and reaction time 8 h.Under the above-mentioned conditions,the yield of compound Ⅲ was 56.8%.Compound Ⅳ with a yield of 87.6%was obtained from compound Ⅲ reacted in sodium methoxide/methanol solution by removing the tetraacetyl group.During cigarette smoking,the transfer rate of isoeugenol from the thermal decomposition of compound Ⅳ to the mainstream smoke particle phase was 3.2%.
关键词
离子液体/相转移催化/糖苷化/异丁香酚-β-D-葡萄糖苷/热裂解转移率/香料与香精Key words
ionic liquids/phase transfer catalysis/glycosylation/isoeugenol-β-D-glucoside/pyrolysis transfer rate/perfumes and essences引用本文复制引用
基金项目
中国烟草总公司重大科技项目(110202201053SJ-03)
河南省科技攻关计划项目(192102110212)
出版年
2024
NETL
NSTL
维普
万方数据