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

作　　者：张改红 徐月莹 石栋栋 杨鹏飞 黄申 毛多斌 ZHANG Gaihong;XU Yueying;SHI Dongdong;YANG Pengfei;HUANG Shen;MAO Duobin(School of Food and Bioengineering,Zhengzhou University of Light Industry,Zhengzhou 450002,Henan,China)

机构地区：[1]郑州轻工业大学食品与生物工程学院,河南郑州450002

出　　处：《精细化工》2024年第2期420-426,457,共8页Fine Chemicals

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)。

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%。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). Compound Ⅳ 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 

分 类 号：O629.13[理学—有机化学] TS426[理学—化学]