61252-49-1

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3α-(ethoxycarbonyloxy)-7α-(hydroxyl)-5β-cholanoate is used as an intermediate in the synthesis of α-Muricholic Acid for its role in the pharmaceutical industry. This bile acid metabolite is significant in the study and treatment of various liver and gallbladder disorders, as well as in the development of diagnostic tools for related conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, methyl 3α-(ethoxycarbonyloxy)-7α-(hydroxyl)-5β-cholanoate is utilized as a key compound for the production of other related molecules and pharmaceuticals. Its unique structure allows for further modification and functionalization, making it a valuable building block in the synthesis of complex organic molecules.
Used in Research and Development:
Methyl 3α-(ethoxycarbonyloxy)-7α-(hydroxyl)-5β-cholanoate is also used in research and development for the study of bile acid metabolism and its implications in human health and disease. Understanding the role of α-Muricholic Acid and related metabolites can lead to the discovery of new therapeutic targets and the development of novel treatments for various medical conditions.

Upstream product

• 3057-04-3 chenodeoxycholic acid methyl ester 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 96475-64-8 methyl 5β-3α-ethoxycarbonyloxy-7-carbonylcholanate 
• 66225-78-3 glycoβ-muricholic acid 
• 1249-75-8 methyl lithocholate 

Relevant academic research and scientific papers

Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

3α-Hydroxyl-7α-(4-pentenoyloxy)-5β-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3α-(ethoxycarbonyloxy)-7α-(allyloxycarbonyloxy)-5β-cholanoate (7) has led us to compare the spectroscopic difference of the 7α-(allyloxycarbonyloxy) group versus the 7α-(4-pentenoyloxy) group. The molecular structures of these compounds were confirmed by X-ray crystallography. Methyl 3α-(ethoxycarbonyloxy)-7α-(allyloxycarbonyloxy)-5β-cholanoate was obtained by a method, which may prove useful in the synthesis of 14C-labeled derivatives for metabolic studies.

INHIBITORS OF THE FARNESOID X RECEPTOR AND USES IN MEDICINE

Disclosed are inhibitors of the farnesoid X receptor, for example of formula (I), wherein R1, R2, R4, X, Y, Z, m, and n are as defined herein, which are useful in treating or preventing obesity, type 2 diabetes/insulin resistance and non alcoholic fatty liver disease in a mammal in need thereof. Also disclosed is a composition comprising a pharmaceutically suitable carrier and at least one compound of the invention, a method of method of inhibiting a farnesoid X receptor in a mammal, and a method of treating or preventing obesity in a mammal.

Chemical synthesis of 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid: An internal standard for mass spectrometric analysis of the abnormal Δ5-bile acids occurring in Niemann-Pick disease

In Niemann-Pick disease, type C1, increased amounts of 3β,7β-dihydroxy-5-cholenoic acid are reported to be present in urinary bile acids. The compound occurs as a tri-conjugate, sulfated at C-3, N-acetylglucosamidated at C-7, and N-acylamidated with taurine or glycine at C-24. For sensitive LC-MS/MS analysis of this bile acid, a suitable internal standard is needed. We report here the synthesis of a satisfactory internal standard, 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid (as the disodium salt). The key reactions involved were (1) the so-called "second order" Beckmann rearrangement (one-carbon degradation at C-24) of hyodeoxycholic acid (HDCA) 3,6-diformate with sodium nitrite in a mixture of trifluoroacetic anhydride and trifluoroacetic acid, (2) simultaneous inversion at C-3 and elimination at C-6 of the ditosylate derivatives of the resulting 3α,6α-dihydroxy-24-nor-5β-cholanoic acid with potassium acetate in aqueous N,N-dimethylformamide, and (3) regioselective sulfation at C-3 of an intermediary 3β,7β-dihydroxy-24-nor-Δ5 derivative using sulfur trioxide-trimethylamine complex. Overall yield of the desired compound was 1.8% in 12 steps from HDCA.