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Synthesis of 7-ketolithocholic acid via indirect electrooxidation of chenodeoxycholic acid

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Abstract

7-Ketolithocholic acid was synthesized by indirect electrooxidation of chenodeoxycholic acid using the medium of Br−/Br2. Some important factors such as anode material, solvent, initial concentration of chenodeoxycholic acid, current density, electrolysis time have been investigated in detail. By comparing the experiment results, it can be concluded that productivity and current efficiency in the divided electrolytic cell are higher than that in the undivided electrolytic cell. The optimized process conditions have been found to be: the anode material PbO2/Ti, the solvent acetonitrile, and initial concentration of chenodeoxycholic acid 23.8–31.8 mg/mL, current density 95.2–142.9 A/m2. The current efficiency could reach 85% and the productivity of 7-ketolithocholic acid could reach 83%. The melting point, IR spectrum, 1H NMR, 13C NMR and EI-MS were used to characterize the product. The analytical results confirm that the product is 7-ketolithocholic acid.

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Acknowledgements

The authors wish to thank Prof. Xin-sheng Zhang and Dr.Yuan-hang Qin (UNILAB Research Centre of Chemical Reaction Engineering, East China University of Science & Technology) for kindly providing Electrochemical Workstation for Cyclic voltammetry experiments.

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Authors and Affiliations

  1. State Key Laboratory of Bioreactor Engineering, Department of Biochemical Engineering, East China University of Science & Technology, 130 Meilong Road, 200237, Shanghai, China

    Hongbin Zhao, He Tian, Yonghong Jin & Xuejun Cao

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  1. Hongbin Zhao
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  2. He Tian
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  3. Yonghong Jin
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  4. Xuejun Cao
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Correspondence to Xuejun Cao.

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Zhao, H., Tian, H., Jin, Y. et al. Synthesis of 7-ketolithocholic acid via indirect electrooxidation of chenodeoxycholic acid. J Appl Electrochem 40, 1307–1316 (2010). https://doi.org/10.1007/s10800-010-0076-z

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  • DOI: https://doi.org/10.1007/s10800-010-0076-z

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