Citation: Dou Qian, Yan Peng, Liu Zhiling, Zhang Wei. Synthesis of Ursodeoxycholic Acid[J]. Chemistry, ;2018, 81(8): 720-726. shu

Synthesis of Ursodeoxycholic Acid

Research Institute of Shanxi Yanchang Petroleum(Group) Co., Ltd, Xi'an 710075

Corresponding author: Zhang Wei, ycsy_zw@163.com
Received Date: 13 March 2018
Accepted Date: 17 April 2018

Figures(6)

Using inexpensive and readily available hyodeoxycholic acid (HDCA) as the starting material and with the Shapiro reaction as a key step, ursodeoxycholic acid was successfully synthesized by a series of reactions including esterification, selective oxidation, epoxidation, and deprotection. The total yield was 25.8%. The whole procedure was further modified to make steps shorter through silyl protection, Rubottom oxidation and Clemmensen reduction, with an overall yield of 28.8%. The structures of all synthetic compounds were identified by ¹H NMR, ¹³C NMR and HRMS. The aggregation behavior of similar bile acid salts with pyrene fluorescent probe was studied, the results showed that critical micelle concentration (CMC) value is only related to the number of hydroxyl group instead of configuration.
- Ursodeoxycholic acid,
- Critical micelle concentration
1. [1]
  D Kritchevsky. The Bile Acids-Chemistry, Physiology and Metabolism; Plenum Press:New York, 1971.
2. [2]
3. [3]
4. [4]
  A Colalillo, D Verga. Gastroenterology, 1980, 78(6):1412~1418.
5. [5]
  A Crosignani, K D Setchell, P Invernizzi et al. Pharmacokinet, 1996, 30(5):333~358.
6. [6]
7. [7]
  J Ren, Y C Wang, J L Wang et al. Steroids, 2013, 78(1):53~58.
8. [8]
  P Pedrini, E Andreotti, A Guerrini et al. Steroids, 2006, 71(3):189~198.
9. [9]
  P P Giovannini, A Grandini, D Perrone et al. Steroids, 2008, 73(14):1385~1390.
10. [10]
  A Medici, P Pedrini, E Bianchini et al. Steroids, 2002, 67(1):51~56.
11. [11]
  W S Zhou, Z Q Wang, B Jiang. J. Chem. Soc., Perkin Transac., 1990, 1:1~3.
12. [12]
  P Hohenberg, W Kohn. Phys. Rev., 1964, 136(3B):864~870.
13. [13]
  M Levy. PNAS, 1979, 76(12):6062~6065.
14. [14]
  A M Sousa, W S Coutinho, A F Lima et al. J. Chem. Phys., 2015, 142(7):703~704.
15. [15]
  Q Zhou, Y Li. J. Am. Chem. Soc., 2015, 137(32):10182~10189.
16. [16]
  S Visitsatthawong, P Chenprakhon, P Chaiyen et al. J. Am. Chem. Soc., 2015, 137(29):9363~9374.
17. [17]
  M J Frisch, G W Trucks, H B Schlegel et al. Gaussian 09, Revision A.1; Gaussian, Inc:Pittsburgh, 2009.
18. [18]
  Q Wang, J Zhao, X F Wang. J. Phys. Chem. A, 2015, 119(11):2244~2252.
19. [19]
  Y F Dai, Z Y Li, J L Yang. J. Phys. Chem. C, 2014, 118(6):3313~3318.
20. [20]
  K C Nicolaou, Z Yang, J Liu et al. Nature, 1994, 367(2):630~634.
21. [21]
  A Guillemette, A Francois. DE:2950481, 1980.
22. [22]
  M Samrat, M Uday. Org. Lett., 2004, 6(1):31~34.
23. [23]
  E Hauser. Helv. Chim. Acta, 1960, 43:1595~1600.
24. [24]
  D Prasad, S Chetan, G Salunke et al. Steroids, 2011, 76(12):1397~1399.
25. [25]
  A P Santos, A Z Panagiotopoulos. J. Phys. Chem., 2016, 144(4):709.
26. [26]
  P Karamanis, C Pouchan. J. Phys. Chem. C, 2012, 116(21):11808~11819.
27. [27]
  Y Wang, L T Cheng. J. Phys., Chem.1992, 96(4):1530~1532.
1. [1]
  Guoze Yan , Bin Zuo , Shaoqing Liu , Tao Wang , Ruoyu Wang , Jinyang Bao , Zhongzhou Zhao , Feifei Chu , Zhengtong Li , Yamauchi Yusuke , Melhi Saad , Xingtao Xu . Opportunities and Challenges of Capacitive Deionization for Uranium Extraction from Seawater. Acta Physico-Chimica Sinica, 2025, 41(4): 2404006-0. doi: 10.3866/PKU.WHXB202404006
2. [2]
  Cunling Ye , Xitong Zhao , Hongfang Wang , Zhike Wang . A Formula for the Calculation of Complex Concentrations Arising from Side Reactions and Its Applications. University Chemistry, 2024, 39(4): 382-386. doi: 10.3866/PKU.DXHX202310043
3. [3]
  Ruilin Han , Xiaoqi Yan . Comparison of Multiple Function Methods for Fitting Surface Tension and Concentration Curves. University Chemistry, 2024, 39(7): 381-385. doi: 10.3866/PKU.DXHX202311023
4. [4]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
5. [5]
  Fanpeng Shang , Jiantuo Chen . 多视角分析DMPE盘状双层胶束——第38届中国化学奥林匹克(初赛)第4题解析. University Chemistry, 2025, 40(8): 388-393. doi: 10.12461/PKU.DXHX202410034
6. [6]
  Zhihuan XU , Qing KANG , Yuzhen LONG , Qian YUAN , Cidong LIU , Xin LI , Genghuai TANG , Yuqing LIAO . Effect of graphene oxide concentration on the electrochemical properties of reduced graphene oxide/ZnS. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1329-1336. doi: 10.11862/CJIC.20230447
7. [7]
  Zeqiu Chen , Limiao Cai , Jie Guan , Zhanyang Li , Hao Wang , Yaoguang Guo , Xingtao Xu , Likun Pan . Advanced electrode materials in capacitive deionization for efficient lithium extraction. Acta Physico-Chimica Sinica, 2025, 41(8): 100089-0. doi: 10.1016/j.actphy.2025.100089
8. [8]
  Xiaochen Zhang , Fei Yu , Jie Ma . Cutting-Edge Applications of Multi-Angle Numerical Simulations for Capacitive Deionization. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-0. doi: 10.3866/PKU.WHXB202311026
9. [9]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
10. [10]
  Hongyi Zhang , Zhihong Shi , Zhijun Zhang . A New Strategy for “De-formulized” Calculation of Dynamic Buffer Capacity in Analytical Chemistry Education. University Chemistry, 2024, 39(3): 390-394. doi: 10.3866/PKU.DXHX202309030
11. [11]
  Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
12. [12]
  Jingyi Xie , Qianxi Lü , Weizhen Qiao , Chenyu Bu , Yusheng Zhang , Xuejun Zhai , Renqing Lü , Yongming Chai , Bin Dong . Enhancing Cobalt―Oxygen Bond to Stabilize Defective Co₂MnO₄ in Acidic Oxygen Evolution. Acta Physico-Chimica Sinica, 2024, 40(3): 2305021-0. doi: 10.3866/PKU.WHXB202305021
13. [13]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
14. [14]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
15. [15]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
16. [16]
  Fa Wang , Yu Chen , Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024
17. [17]
  Hao Chen , Dongyue Yang , Gang Huang , Xinbo Zhang . Progress on Liquid Organic Electrolytes of Li-O₂ Batteries. Acta Physico-Chimica Sinica, 2024, 40(7): 2305059-0. doi: 10.3866/PKU.WHXB202305059
18. [18]
  Weicheng Feng , Jingcheng Yu , Yilan Yang , Yige Guo , Geng Zou , Xiaoju Liu , Zhou Chen , Kun Dong , Yuefeng Song , Guoxiong Wang , Xinhe Bao . Regulating the High Entropy Component of Double Perovskite for High-Temperature Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(6): 2306013-0. doi: 10.3866/PKU.WHXB202306013
19. [19]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
20. [20]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105

Get Citation

PDF

XML

Metrics

PDF Downloads(54)
Abstract views(4421)
HTML views(1514)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142