S-(-)-尼古丁-己二酸盐的制备、特性及其应用研究  

Preparation,characteristics and application of S-(-)-nicotine adipic acid salt

作　　者：肖智心 李江 黄晓江 何世波 刘明星[1] XIAO Zhi-xin;LI Jiang;HUANG Xiao-jang;HE Shi-bo;LIU Ming-xing(School of Life and Health Sciences,Hubei University of Technology,Wuhan 430068,China;Hubei Heno Biological Engineering Co.,Ltd.,Enshi 445000,China)

机构地区：[1]湖北工业大学生命科学与健康工程学院,湖北武汉430068 [2]湖北和诺生物工程股份有限公司,湖北恩施445000

出　　处：《化学研究与应用》2024年第9期2184-2189,共6页Chemical Research and Application

基　　金：恩施州“揭榜制”科技计划项目(202202)资助。

摘　　要：S-(-)-尼古丁的获取主要是通过从烟叶等植物中提取,获取途径受限,本研究以2′-羟基尼古丁为原料通过还原、化学拆分制备S-(-)-尼古丁;选用己二酸与S-(-)-尼古丁通过超声法制备S-(-)-尼古丁-己二酸盐,优化了合成工艺。产物利用ESI-MS、^(1)H NMR、HPLC进行表征;采用HPLC进行抗氧化性分析;利用热重分析仪进行热稳定性分析。结果表明在反应的最佳工艺条件下S-(-)-尼古丁总产率达55.1%,比旋光度为-141.5°,光学纯度为99.23%;S-(-)-尼古丁-己二酸盐的产率达94.4%,纯度为99.36%;S-(-)-尼古丁-己二酸盐的抗氧化性和热稳定性均优于S-(-)-尼古丁。本研究提供了一条切实可行的S-(-)-尼古丁及其己二酸盐的合成路线;S-(-)-尼古丁-己二酸盐有效避免了S-(-)-尼古丁易氧化、受热不稳定等不足,具有良好的应用前景。The acquisition of S-(-)-nicotine is primarily achieved through extraction from plants such as tobacco,with limited sources.This study explored the preparation of S-(-)-nicotine from 2'-hydroxy nicotine through reduction and chemical cleavage.Adipic acid was chosen to form the S-(-)-nicotine adipic acid salt using ultrasound-assisted synthesis,and the synthetic process was optimized.The products were characterized using ESI-MS,^(1)H NMR,and HPLC.Antioxidant analysis was conducted using HPLC,and thermal stability were evaluated using a thermogravimetric analyzer.Results indicated that under optimal conditions,the total yield of S-(-)-nicotine reached 55.1%,with a specific rotation of-141.5°,and an optical purity of 99.23%.The yield of S-(-)-nicotine adipic acid salt was 94.4%,with a purity of 99.36%.The antioxidant and thermal stability of S-(-)-nicotine adipic acid salt were superior to S-(-)-nicotine.This study provided a practical synthesis route for S-(-)-nicotine and its adipic acid salt.The S-(-)-nicotine adipic acid salt effectively avoided such as oxidation susceptibility and thermal instability associated with S-(-)-nicotine,presenting promising applications in various fields.

关 键 词：S-(-)-尼古丁 S-(-)-尼古丁-己二酸盐 抗氧化性 热稳定性 

分 类 号：O626.32[理学—有机化学]