566-17-6

Usage

Uses

Used in Pharmaceutical Industry:
5-BETA-CHOLANIC ACID-7-ALPHA, 12-ALPHA-DIOL is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly those related to cholesterol and bile acid metabolism. Its unique structure allows for the development of drugs that can target specific pathways involved in these processes.
Used in Diagnostic Applications:
In the field of diagnostics, 5-BETA-CHOLANIC ACID-7-ALPHA, 12-ALPHA-DIOL is used for comprehensive bile acid profiling in hereditary intrahepatic cholestasis. This condition is characterized by impaired bile formation and flow, leading to the accumulation of bile acids in the liver and potentially causing liver damage. 5-BETA-CHOLANIC ACID-7-ALPHA, 12-ALPHA-DIOL aids in the identification and monitoring of bile acid levels, which can help in the diagnosis and management of the disease.
Used in Research and Development:
5-BETA-CHOLANIC ACID-7-ALPHA, 12-ALPHA-DIOL is also utilized in research and development for the study of cholesterol and bile acid metabolism, as well as the development of new therapeutic strategies for related medical conditions. Its unique properties make it a valuable tool for understanding the complex interactions between bile acids, cholesterol, and other lipids in the body.

InChI:InChI=1/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1

Upstream product

• 83-44-3 (R)-4-((3R,12S)-3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 
• 88165-73-5 7α-hydroxy-3α-tosyloxy-5β-cholansaeure-24,12α-lacton 
• 88165-75-7 7α-hydroxy-5β-cholansaeure-24,12α-lacton 
• 3701-54-0 methyl 7α,12a-dihydroxy-5β-cholan-24-oate 
• 84325-08-6 7-oxo-12α-hydroxy-5β-cholan-24-oic acid 
• 4947-65-3 methyl 3-keto-7,12-diacetylcholate 
• 21059-35-8 7,12-dioxo-5β-cholan-24-oic acid 
• 64-19-7 acetic acid 
• 6818-44-6 methyl 3,7,12-triacetoxycholan-24-oate 
• 1448-36-8 methyl cholate 
• 69889-89-0 methyl 7,12-diacetoxycholate 
• 81-25-4 cholic acid 
• 2304-89-4 7α,12α-dihydroxy-3-oxocholanoic acid 
• 14772-99-7 3-oxo cholic acid methyl ester 

Downstream Products

• 84413-81-0 7β,12α-dihydroxy-5β-cholan-24-oic acid 

Relevant academic research and scientific papers

7β,12β-dihydroxy-5β-cholan-24-oic acid as an internal standard for quantitative determination of bile acids by gas chromatography

In order to find an artificial internal standard compound for quantitative determination of bile acids by gas chromatography, 7α,12α-, 7α,12β-, 7β,12α- and 7β,12β-dihydroxy-5β-cholan-24-oic acids were chemically synthesized with cholic acid as the first starting material. The gas chromatographic retention time of 7β,12β-dihydroxy-5β-cholan-24-oic acid (ββ-isomer) was more different from that of natural bile acids than the other isomers. Moverover, ββ-isomer was extracted in the same fraction as the bile acids from urine, and no urinary substance had the same retention time as ββ-isomer. No artifact was produced from ββ-isomer during the analysis procedure. It was concluded that the ββ-isomer is an internal standard compound with certain advantages for the quantitative determination of bile acids in urine by gas chromatography, irrespective of the recovery rate during the analysis procedure.

Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids

The asymmetric epoxidation of substituted cinnamic acids has been obtained in the presence of different keto bile acid derivatives as optically active carbonyl inducers and Oxone as oxygen source. Predominant or almost exclusive formation of both enantiomeric epoxides is obtained (ee up to 95%) depending on the specific substitution at carbons C(7) and C(12) of the bile acid.

DARSTELLUNG VON CHOLSAEURELACTONEN

The 8-membered cyclic 24,12-lactones of cholic- and deoxycholic acid, previously prepared only in poor yield are easily synthesized by the reaction of the appropriate acids with arylsulfonylchloride in pyridine.Chenodeoxycholic acid is converted into a di