2242-12-8

Upstream product

• 81644-38-4 methyl 3-oxo-5β-chol-11-en-24-oate 
• 1053-37-8 3β-hydroxy-5β-cholen-(11)-oic acid-(24) 
• 423767-61-7 3-keto-5β-chol-11-enic acid 
• 81644-41-9 3β-hydroxy-5β-cholen-(11)-oic acid-(24)-methyl ester 
• 108-24-7 acetic anhydride 
• 27240-83-1 methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate 
• 3245-38-3 methyl deoxycholate 
• 83-44-3 Deoxycholic acid 
• 1053-37-8 lithocholenic acid 
• 7647-01-0 hydrogenchloride 
• 7751-05-5 3α-acetoxy-11β-hydroxy-5β-cholan-24-oic acid methyl ester 
• 64-19-7 acetic acid 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 141-52-6 sodium ethanolate 

Downstream Products

• 62797-60-8 3α-hydroxy-5β-chol-9(11)-en-24-oic acid 
• 3253-69-8 methyl 3α-acetoxy-5β-cholan-24-oate 
• 434-13-9 Lithocholic acid 
• 1053-37-8 lithocholenic acid 
• 4472-02-0 methyl 3β-hydroxy-5β-chol-9(11)-ene-12-one-24-oate acetate 
• 122441-65-0 methyl 3β-hydroxy-5β-cholan-11-one-24-oate acetate 
• 4472-02-0 methyl 3α-acetoxy-12-oxo-5β-chol-9(11)-en-24-oate 
• 4651-66-5 methyl 3α-acetoxy-11-oxo-5β-cholan-24-oate 

Relevant academic research and scientific papers

Chemical Synthesis of Rare Natural Bile Acids: 11α-Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids

A method for the preparation of 11α-hydroxy derivatives of lithocholic and chenodeoxycholic acids, recently discovered to be natural bile acids, is described. The principal reactions involved were (1) elimination of the 12α-mesyloxy group of the methyl esters of 3α-acetate-12α-mesylate and 3α,7α-diacetate-12α-mesylate derivatives of deoxycholic acid and cholic acid with potassium acetate/hexamethylphosphoramide; (2) simultaneous reduction/hydrolysis of the resulting △11-3α-acetoxy and △11-3α,7α-diacetoxy methyl esters with lithium aluminum hydride; (3) stereoselective 11α-hydroxylation of the △11-3α,24-diol and △11-3α,7α,24-triol intermediates with B2H6/tetrahydrofuran (THF); and (4) selective oxidation at C-24 of the resulting 3α,11α,24-triol and 3α,7α,11α,24-tetrol to the corresponding C-24 carboxylic acids with NaClO2 catalyzed by 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and NaClO. In summary, 3α,11α-dihydroxy-5β-cholan-24-oic acid and 3α,7α,11α-trihydroxy-5β-cholan-24-oic acid have been synthesized and their nuclear magnetic resonance (NMR) spectra characterized. These compounds are now available as reference standards to be used in biliary bile acid analysis.

The synthesis and antitumor activity of lithocholic acid and its derivatives

In this paper, a new and concise synthetic route of lithocholic acid (LCA) using commercially available steroid source deoxycholic acid is reported. A series of amide derivatives of LCA were also synthesized and investigated for their activity against the growth of MCF-7 and MCF-7/ADR cells using the sulforhodamine B assay. For MCF-7, the most potent compound 20 showed a 20-fold higher antitumor activity than LCA. For MCF-7/ADR, the most potent compound 24 showed a 22-fold higher antitumor activity than LCA. The transwell migration assay of 20 was evaluated on MDA-MB-231 cells. The colony formation and apoptosis assays of 20 were performed on MCF-7 and MCF-7/ADR cell lines.

Synthesizing method of lithocholic acid

The invention discloses a synthesizing method of lithocholic acid. The synthesizing method is characterized in that deoxycholic acid is used as the raw material, and the deoxycholic acid is subjected to reactions such as methyl esterification protection, acetic anhydride protection of 3 hydroxyl groups, dewatering, hydrogenation and hydrolysis to synthesize the lithocholic acid. The synthesizing method is simple in step, few in side reaction, high in yield, easy in raw material obtaining, suitable for industrial production, and capable of solving the problems that the prior art is excessively high in synthesizing cost, low in yield and not suitable for large-scale industrial production.