Issue
Korean Journal of Chemical Engineering,
Vol.31, No.7, 1276-1280, 2014
Preparation of ursodeoxycholic acid by direct electro-reduction of 7-ketolithocholic acid
A novel method of producing ursodeoxycholic acid was developed through direct electro-reduction of 7-ketolithocholic acid in a divided electrolytic cell. Titanium ruthenium mesh electrode was used as the anode, while high purity lead plate was used as the cathode. The process was optimized with regards to the electrolyte, temperature, concentration of methanol, current density and concentration of anolyte. When potassium bromide was used as the electrolyte, the saturated solution of 7-ketolithocholic acid in 85-93% (v/v) methanol, current density 9.52-28.6 A/m2 and concentration of anolyte at 4-6% (w/w), the maximum percentage yield of ursodeoxycholic acid could be 47%. The method will provide a potential approach for large-scale production of ursodeoxycholic acid.
[References]
  1. Talwalkar JA, Lindor KD, Lancet, 362, 53, 2003
  2. Hepatol J, European Association for the Study of the Liver, 51, 237, 2009
  3. Salvioli G, Igimi H, Carey MC, J. Lipid. Res., 24, 701, 1983
  4. Shiraki K, Ito T, Sugimoto K, Fuke H, Inoue T, Miyashita K, Yamanaka T, Suzuki M, Nabeshima K, Int. J. Mol. Med., 16, 729, 2005
  5. Liu F, Cheng Y, Wu J, Tauschel HD, Duan RD, Cancer Lett., 235, 141, 2006
  6. Galsky J, Bansky G, Holubova T, Konig J, J. Clin. Gastroenterol., 28, 249, 1999
  7. Poupon RE, Lindor KD, Cauch DK, Dickson ER, Poupon R, Heathcote E, J. Gastroenterol., 113, 884, 1997
  8. Santos VN, Lanzoni VP, Szejnfeld J, Shigueoka D, Parise ER, Braz. J. Med. Biol. Res., 36, 723, 2003
  9. Shoda M, J. Biochem., 7, 505, 1927
  10. Kanazawa T, Shimazaki A, Sato T, Hoshino T, Proc. Jpn. Acad., 30, 391, 1954
  11. Claudio G, Francesco M, Mariano M, Giulio P, US Patent, 4,486,352, 1984
  12. Kubota N, Mashita N, Japan Patent, 2,282,393, 1990
  13. Hattori M, Mikami K, Sekine T, Japan Patent, 5,032,692, 1993
  14. Bharucha R, Slemon E, US Patent, 4,547,271, 1985
  15. Hatsutori, Japan Patent, 6,002,184, 1994
  16. Terada M, Minami J, Abe N, Sato M, Horie Y, Komiyama M, Japan Patent, 60,217,899, 1985
  17. Zhao HB, Tian H, Jin YH, Cao XJ, J. Appl. Electrochem., 40(7), 1307, 2010