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Anodic electrochemical oxidation of cholic acid.

Anodic electrochemical oxidation of cholic acid.

Steroids (2001-01-09)

A Medici, P Pedrini, A De Battisti, G Fantin, M Fogagnolo, A Guerrini

摘要

Regioselectivity in the anodic electrochemical oxidation of cholic acid with different anodes is described. The oxidation with PbO(2) anode affords the dehydrocholic acid in quantitative yield after 22 h. 3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholan-24-oic acid (59%) and 3alpha-hydroxy-7,12-dioxo-5beta-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 3alpha,12alpha-dihydroxy-7-oxo-5beta-cholan-24-oic acid (96%) while the 3alpha,7alpha-dihydroxy-12-oxo-5beta-cholan-24-oic acid (34%) is obtained together with the other oxo acids.

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铂, foil, not light tested, 100x100mm, thickness 0.0125mm, as rolled, 99.95%

铂, foil, 25x25mm, thickness 0.1mm, as rolled, 99.99+%

铂, foil, 25x25mm, thickness 0.25mm, as rolled, 99.99+%

铂, foil, 25x25mm, thickness 0.25mm, as rolled, 99.95%

铂, foil, 15x15mm, thickness 0.2mm, as rolled, 99.95%

铂, foil, 50x50mm, thickness 0.1mm, as rolled, 99.95%

铂, foil, 25x25mm, thickness 0.125mm, as rolled, 99.95%

铂, foil, 30x30mm, thickness 0.2mm, as rolled, 99.95%

铂, foil, 25x25mm, thickness 0.25mm, as rolled, 99.999%

铂, foil, 50x50mm, thickness 0.125mm, as rolled, 99.99+%

铂, foil, 25x25mm, thickness 0.1mm, as rolled, 99.95%

铂, foil, 50x50mm, thickness 0.1mm, as rolled, 99.99+%

铂, foil, 50x50mm, thickness 0.125mm, as rolled, 99.95%

铂, foil, 10mm disks, thickness 0.1mm, as rolled, 99.99+%

铂, foil, 25x25mm, thickness 0.125mm, as rolled, 99.99+%

铂, foil, 10mm disks, thickness 0.125mm, as rolled, 99.95%

铂, foil, 6mm disks, thickness 0.025mm, as rolled, 99.95%

铂, foil, not light tested, 100x100mm, thickness 0.01mm, as rolled, 99.95%

铂, foil, 0.1m coil, thickness 0.025mm, coil width .85mm, as rolled, 99.95%

铂, foil, 4mm disks, thickness 0.004mm, as rolled, 99.95%

铂, foil, 4mm disks, thickness 0.125mm, as rolled, 99.99+%

铂, foil, 0.05m coil, thickness 0.045mm, coil width .75mm, as rolled, 99.95%

铂, foil, 0.1m coil, thickness 0.025mm, coil width 5mm, as rolled, 99.95%

铂, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.95%

铂, foil, 0.2m coil, thickness 0.045mm, coil width .75mm, as rolled, 99.95%

铂, foil, not light tested, 50x50mm, thickness 0.01mm, as rolled, 99.95%

铂, foil, not light tested, 50x50mm, thickness 0.025mm, as rolled, 99.95%

铂, foil, 0.05m coil, thickness 0.025mm, coil width 1.2mm, as rolled, 99.95%

铂, foil, 0.1m coil, thickness 0.025mm, coil width .4mm, as rolled, 99.95%

铂, foil, 0.1m coil, thickness 0.2mm, coil width 5mm, as rolled, 99.95%