Regioselectivity in the anodic electrochemical oxidation of cholic acid with different anodes is described. The oxidation with PbO2 anode affords the dehydrocholic acid in quantitative yield after 22 h. 3α,12α-Dihydroxy-7-oxo-5β-cholan-24-oic acid (59%) and 3α-hydroxy-7,12-dioxo-5β-cholan-24-oic acid (51%) are obtained stopping the reaction at lower time. The rate of the OH-oxidation is C7 > C12 > C3. The electro-oxidation with platinum foil anode gives selectively the 7-ketocholic acid in 40% yield. On the other hand, the graphite plate anode, varying the reaction conditions, produces selectively the dehydrocholic acid in quantitative yield or the 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid (96%) while the 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid (34%) is obtained together with the other oxo acids. Copyright © 2001 Elsevier Science Inc.

Anodic electrochemical oxidation of cholic acid

Medici A.;Pedrini P.;De Battisti A.;Fantin G.;Fogagnolo M.;Guerrini A.
2001

Abstract

Regioselectivity in the anodic electrochemical oxidation of cholic acid with different anodes is described. The oxidation with PbO2 anode affords the dehydrocholic acid in quantitative yield after 22 h. 3α,12α-Dihydroxy-7-oxo-5β-cholan-24-oic acid (59%) and 3α-hydroxy-7,12-dioxo-5β-cholan-24-oic acid (51%) are obtained stopping the reaction at lower time. The rate of the OH-oxidation is C7 > C12 > C3. The electro-oxidation with platinum foil anode gives selectively the 7-ketocholic acid in 40% yield. On the other hand, the graphite plate anode, varying the reaction conditions, produces selectively the dehydrocholic acid in quantitative yield or the 3α,12α-dihydroxy-7-oxo-5β-cholan-24-oic acid (96%) while the 3α,7α-dihydroxy-12-oxo-5β-cholan-24-oic acid (34%) is obtained together with the other oxo acids. Copyright © 2001 Elsevier Science Inc.
2001
Medici, A.; Pedrini, P.; De Battisti, A.; Fantin, G.; Fogagnolo, M.; Guerrini, A.
File in questo prodotto:
File Dimensione Formato  
70. ST 2001.pdf

solo gestori archivio

Descrizione: Full text editoriale
Tipologia: Full text (versione editoriale)
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 154.22 kB
Formato Adobe PDF
154.22 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11392/1203815
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 17
social impact