S-EMCA

Base Information

• Chemical Name: S-EMCA
• CAS No.: 1199796-29-6
• Molecular Formula: C₂₇H₄₆O₅
• Molecular Weight: 450.659
• Mol file: 1199796-29-6.mol

Synonyms:

Chemical Property of S-EMCA

Chemical Property:

• Melting Point: 150-152℃
• Boiling Point: 602.8±55.0 °C(Predicted)
• PKA: 4.80±0.21(Predicted)
• Density: 1.128±0.06 g/cm3(Predicted)

Purity/Quality:

>98% ^*data from raw suppliers

6α-Ethyl-23(S)-methylcholicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: INT 777 is an inhibitor of TGR5 receptor, which is a transmembrane G protein-coupled receptor expressed in brown adipose tissue and muscle and activated by bile acid.

Technology Process of S-EMCA

There total 2 articles about S-EMCA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

C28H48O5 → INT-777 (1199796-29-6) + 6α-ethyl-23(S)-methyl-3α,7α,12α trihydroxy-5β-cholan-24-oic acid (1198786-98-9)

Guidance literature:

With sodium hydroxide; In methanol; at 45 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm901390p

Reference yield: 41.0%

methyl 3α,7α,12α-trimethoxymethyloxy-6α-ethyl-5β-cholan-24-oate (1227639-47-5) + methyl iodide (74-88-4) → INT-777 (1199796-29-6)

Guidance literature:

methyl 3α,7α,12α-trimethoxymethyloxy-6α-ethyl-5β-cholan-24-oate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

upstream raw materials:

methyl 3α,7α,12α-trimethoxymethyloxy-6α-ethyl-5β-cholan-24-oate

methyl iodide

Refernces

• 1、 Pellicciari, Roberto,Gioiello, Antimo,Macchiarulo, Antonio,Thomas, Charles,Rosatelli, Emiliano,Natalini, Benedetto,Sardella, Roccaldo,Pruzanski, Mark,Roda, Aldo,Pastorini, Elisabetta,Schoonjans, Kristina,Auwerx, Johan. "Discovery of 6α-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity". supporting information; experimental part. p. 7958 - 7961. Retrieved 2010/08/22.