稳定同位素标记[2H4]-β-紫罗兰酮的合成及表征  

Synthesis and Characterization of Stabilized Isotope [2H4]-β-Ionone

作　　者：白冰 钟闻英 黄备备 张改红 贾春晓 毛多斌 BAI Bing;ZHONG Wen-ying;HAUNG Bei-bei;ZHANG Gai-hong;JIA Chun-xiao;MAO Duo-bin(School of Food&Biological Engineering,Zhengzhou University of Light Industry,Zhengzhou 450000,China;College of Material and Chem ical Engineering,Zhengzhou University of Light Industry,Zhengzhou 450000,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450000 [2]郑州轻工业大学材料与化学工程学院,河南郑州450000

出　　处：《化学试剂》2020年第3期332-336,共5页Chemical Reagents

基　　金：国家自然科学基金资助项目(21476216);烟草行业烟草工业生物技术重点实验室专项项目(中烟办[2014]334号);河南省科技攻关项目(192102110212)。

摘　　要：以柠檬醛为原料,以D6-丙酮为稳定同位素标记前体物,经碱催化羟醛缩合及酸催化关环反应合成了[2H4]-β-紫罗兰酮,考察了碱和酸的种类、用量及温度对反应的影响,确定了最优路线:先在20%NaOH重水溶液中于55℃反应2 h合成假性紫罗兰酮,再经浓硫酸于-10℃反应10 min合成目标产物,两步总收率为60%。目标化合物结构通过质谱、核磁共振氢谱、核磁共振碳谱、红外光谱进行表征,经高效液相色谱确认化学纯度>99%,经计算同位素丰度为98.1%。该方法所得目标产物可作为稳定同位素稀释分析法中的对照物质。Stabilized isotope-labeled [2H4]-β-ionone was synthesized by using citral as starting material and D6-acetone as a stable isotope-labeled precursor with two steps.The optimal reaction conditions were investigated.The first step was aldol condensation of citral with D6-acetone in the presence of 20% NaOH at 55 ℃ for 2 h.The second step was cyclization of the acquired pseudoionone in the presence of concentrated H2SO4 at-10 ℃ for 10 min.The total yield was 60%.The target compound was confirmed by MS,1HNMR,13CNMR and IR.The chemical purity was 99% detected by HPLC,and the isotope abundance was 98.1% by calculation.The compound could be used as standard in the method of stable isotope dilution.

关 键 词：同位素标记 合成 [2H4]-β-紫罗兰酮 柠檬醛 对照品 

分 类 号：O628.1[理学—有机化学]