姜黄素烟酸酯的绿色合成
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摘要
目的:考察姜黄素烟酸酯的合成及表征,优化其合成工艺路线,为产业化奠定基础。方法:以姜黄素和烟酸为原料,N,N’-二环己基碳二亚胺(DCC)为脱水剂和4-二甲胺基吡啶(DMAP)为催化剂,在室温下合成姜黄素烟酸酯。结果:目标物的化学结构经红外光谱(IR)、液相色谱质谱联用(LC/MS)、氢核磁共振(1H-NMR)表征,本法合成姜黄素烟酸酯的收率达89.4%。结论:改进后的合成工艺操作简便、反应条件温和,重现性好,收率较高,易于放大制备。
Objective: To study the synthesis and characterization of curcumin nicotinate,improve the synthetic route,and lay foundation for the industrialization. Methods: Curcumin nicotinate was synthesized with curcumin and niacin as the raw materials,N,N'-dicyclohexylcarbodiimide (DCC) as the dehydrating agent,and 4-dimethylamino pyridine (DMAP) as the catalyst at room temperature. Results: The chemical structure of target compound was confirmed by infrared spectrum (IR),high performance liquid chromatography-mass spectrometry (LC/MS) and hydrogen nuclear magnetic resonance(1 HNMR),and the yield of curcumin nicotinate was 89.4%.Conclusion: The improvement is simple with mild reaction conditions,good reproducibility and higher yield,and suitable for the industrial production.
Objective: To study the synthesis and characterization of curcumin nicotinate,improve the synthetic route,and lay foundation for the industrialization. Methods: Curcumin nicotinate was synthesized with curcumin and niacin as the raw materials,N,N'-dicyclohexylcarbodiimide (DCC) as the dehydrating agent,and 4-dimethylamino pyridine (DMAP) as the catalyst at room temperature. Results: The chemical structure of target compound was confirmed by infrared spectrum (IR),high performance liquid chromatography-mass spectrometry (LC/MS) and hydrogen nuclear magnetic resonance(1 HNMR),and the yield of curcumin nicotinate was 89.4%.Conclusion: The improvement is simple with mild reaction conditions,good reproducibility and higher yield,and suitable for the industrial production.
引文
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5王华森,怀其勇.姜黄素衍生物的合成及抑菌活性研究[J].天然产物研究与开发,2013,25(2):237-240
6何黎琴,王效山,罗丹.姜黄素烟酸酯的合成[J].化学世界,2011,(3):175-177
7张学景,朱杰,熊晓云,等.白藜芦醇及白藜芦醇烟酸酯的合成[J].中国药学(英文版),2004,13(1):10-13
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9肖峰,李健和.右旋皮考布洛芬的绿色合成与表征[J].中国医药指南,2012,10(29):21-22
10 Kumar S,Narain U,Tripathi S,et al.Syntheses of curcumin bioconjugates and study of their antibacterial activities againstβ-lactamase-producing microorganisms[J].Bioconjugate Chem,2001,12(4):464-469
11李前荣,顾承志,尹浩,等.用DCCDMAP合成N苄氧羰基氨基酸薄荷酯[J].有机化学,2005,25(11):1416-1419
2姚海伦.烟酸姜黄素酯对动脉粥样硬化小鼠脂质调节和炎症反应的初步研究[D].湖南衡阳:南华大学硕士学位论文,2014
3郑自通.烟酸联合姜黄素对高脂血症大鼠的降脂作用及机制研究[D].湖南衡阳:南华大学硕士学位论文,2012
4廖端芳,郑兴,庹勤慧,等.含烟酸姜黄素酯衍生物及其制造方法和用途:中国专利,CN200910042665.8[P].2009-02-13
5王华森,怀其勇.姜黄素衍生物的合成及抑菌活性研究[J].天然产物研究与开发,2013,25(2):237-240
6何黎琴,王效山,罗丹.姜黄素烟酸酯的合成[J].化学世界,2011,(3):175-177
7张学景,朱杰,熊晓云,等.白藜芦醇及白藜芦醇烟酸酯的合成[J].中国药学(英文版),2004,13(1):10-13
8江明星.姜黄素提取及其修饰产物的活性研究[J].安徽合肥:安徽大学硕士学位论文,2011
9肖峰,李健和.右旋皮考布洛芬的绿色合成与表征[J].中国医药指南,2012,10(29):21-22
10 Kumar S,Narain U,Tripathi S,et al.Syntheses of curcumin bioconjugates and study of their antibacterial activities againstβ-lactamase-producing microorganisms[J].Bioconjugate Chem,2001,12(4):464-469
11李前荣,顾承志,尹浩,等.用DCCDMAP合成N苄氧羰基氨基酸薄荷酯[J].有机化学,2005,25(11):1416-1419