Methyl lithocholate

Base Information

• Chemical Name: Methyl lithocholate
• CAS No.: 1249-75-8
• Molecular Formula: C₂₅H₄₂O₃
• Molecular Weight: 390.607
• European Community (EC) Number: 215-002-9
• NSC Number: 63558,8116
• DSSTox Substance ID: DTXSID501315512
• Nikkaji Number: J21.487F
• Wikidata: Q63396421
• ChEMBL ID: CHEMBL260735
• Mol file: 1249-75-8.mol

Synonyms:lithocholic acid, methyl ester;methyl lithocholate;methyl lithocholate, (3beta,5alpha)-isomer;methyl lithocholate, (3beta,5beta)-isomer;methyl lithocholate, 24-(14)C-labeled, (3alpha,5beta)-isomer;methyl lithocholate, 3H-labeled, (3beta,5alpha)-isomer

Chemical Property of Methyl lithocholate

Chemical Property:

• Vapor Pressure: 5.56E-11mmHg at 25°C
• Melting Point: 125-126 °C
• Boiling Point: 474.1°Cat760mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 177.5°C
• PSA: 46.53000
• Density: 1.038g/cm³
• LogP: 5.59550
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 390.31339520
• Heavy Atom Count: 28
• Complexity: 588

Purity/Quality:

99% ^*data from raw suppliers

MethylLithocholate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Uses: Methyl Lithocholate is an derivative of Lithocholic Acid (L469180),a cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

Technology Process of Methyl lithocholate

There total 63 articles about Methyl lithocholate 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: 100.0%

methanol (67-56-1) + Lithocholic acid (434-13-9) → methyl lithocholate (1249-75-8,5405-42-5,15074-01-8,15074-02-9,20231-51-0,63814-53-9,106757-10-2,125412-30-8)

Guidance literature:

With acetyl chloride; at 20 ℃; for 3.3h;

DOI:10.1016/S0968-0896(98)80025-4

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Lithocholic acid (434-13-9) → methyl lithocholate (1249-75-8,5405-42-5,15074-01-8,15074-02-9,20231-51-0,63814-53-9,106757-10-2,125412-30-8)

Guidance literature:

In diethyl ether; at 20 ℃; for 1h;

DOI:10.1134/S1068162006060124

Reference yield: 100.0%

Lithocholic acid (434-13-9) + diazomethyl-trimethyl-silane (18107-18-1) → methyl lithocholate (1249-75-8,5405-42-5,15074-01-8,15074-02-9,20231-51-0,63814-53-9,106757-10-2,125412-30-8)

Guidance literature:

In methanol; hexane; toluene; at 20 ℃;

DOI:10.1016/j.steroids.2012.07.006

upstream raw materials:

methanol

Isolithocholic acid

3α-hydroxy-5α-cholanic acid

3β-hydroxy-5α-cholan-24-oic acid

Downstream raw materials:

24,24-diphenyl-5α-cholanediol-(3α,24)

24,24-diphenyl-5α-cholanediol-(3β,24)

(R)-methyl 4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate

3α-acetoxy-24,24-diphenyl-5β-chol-23-ene

Refernces

• 1、 Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao. "Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite". supporting information. p. 2713 - 2718. Retrieved 2021/06/25.
• 2、 Xie, Qiqiang,Dong, Guangbin. "Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds". supporting information. p. 14422 - 14427. Retrieved 2021/09/29.