Beiträge zur Kenntnis der Konstitution der Tetraoxy-norsterocholansäure

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Abstract
The new acid, tetrahydroxynor-sterocholanic acid, C27H46O6, m. 214[degree], was obtained from the bile of the "Gigi" fish. To prove that the 4 secondary alc. groups were at the C3, C6, C12 and C24 positions, the acid was partially acetylated, and a diacetate, m. 230[degree], obtained. This compound was partially oxidized with CrO3 to give 3,6-diacetoxy-12-ketocholanic acid, m. 210[degree], which after reduction and hydrolysis gave the known hydro-desoxycholic acid. Two of the secondary alc. groups were therefore at the C3 and C6 positions. The 3,6-diacetoxy-12-ketocholanic acid was subjected to dry distillation in vacuo, and an unsaturated acid obtained, which upon hydrogenation gave the known 12-ketocholanic acid, thus establishing the 3d secondary alc. group in the C12 position. By hydrolysis of the 3,6-diacetoxy-12-ketocholanic acid, the 3,6-dihydroxy-12-ketocholanic acid, C24H38O5, m. 190[degree], was formed. The constitution of the new acid was 3,6,12,24-tetrahydroxynor-sterocholanic acid.

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