Methyl 3,7,12-trihydroxycholan-24-oate

Base Information

• Chemical Name: Methyl 3,7,12-trihydroxycholan-24-oate
• CAS No.: 1448-36-8
• Molecular Formula: C25H42 O5
• Molecular Weight: 422.605
• European Community (EC) Number: 215-903-7
• NSC Number: 126794,224329
• DSSTox Substance ID: DTXSID40932412
• Wikidata: Q104984886
• Mol file: 1448-36-8.mol

Synonyms:1448-36-8;Methyl 3,7,12-trihydroxycholan-24-oate;NSC-126794;methyl thiodeoxycholate;Oprea1_471199;SCHEMBL1073655;DTXSID40932412;DLYVTEULDNMQAR-UHFFFAOYSA-N;(R)-methyl 4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate;NSC126794;NSC224329;AKOS000621834;AKOS026750613;NSC-224329;FT-0623768;Methyl-3beta,7beta,12beta-trihydroxy-5beta-cholan-24-oate;Cholan-24-oic acid,7,12-trihydroxy-, methyl ester, (3.alpha.,5.beta.,7.alpha.,12.alpha.)-

Chemical Property of Methyl 3,7,12-trihydroxycholan-24-oate

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 5.49E-14mmHg at 25°C
• Melting Point: 155-156°C
• Boiling Point: 541.6°Cat760mmHg
• PKA: 14?+-.0.70(Predicted)
• Flash Point: 174.9°C
• PSA: 86.99000
• Density: 1.141g/cm³
• LogP: 3.53710
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• Water Solubility.: Insoluble in water. Soluble in medium polarity organic solvents.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 422.30322444
• Heavy Atom Count: 30
• Complexity: 652

Purity/Quality:

99% ^*data from raw suppliers

MethylCholate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• Uses: A bile acid derivative as anti-inflammatory and antitumor agent. Protected Cholic Acid Methyl cholate, is used as a bile acid derivative as anti-inflammatory and antitumor agent.

Technology Process of Methyl 3,7,12-trihydroxycholan-24-oate

There total 45 articles about Methyl 3,7,12-trihydroxycholan-24-oate 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) + cholic acid (81-25-4) → methyl cholate (1448-36-8)

Guidance literature:

With diazomethyl-trimethyl-silane; In methanol; toluene; at 20 ℃; for 2h;

DOI:10.1124/dmd.117.075275

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + cholic acid (81-25-4) → methyl chelate + methyl cholate (1448-36-8)

Guidance literature:

In tetrahydrofuran;

Reference yield: 100.0%

cholic acid (81-25-4) + diazomethyl-trimethyl-silane (18107-18-1) → methyl cholate (1448-36-8)

Guidance literature:

In methanol; hexane; toluene; at 20 ℃;

DOI:10.1016/j.steroids.2012.07.006

upstream raw materials:

methanol

3α,7α,12α-trihydroxy-(5β)-cholan-24-oic acid

3α,7α,12α-trihydroxy-5β-cholanic acid

diazomethane

Downstream raw materials:

3-oxo cholic acid methyl ester

4,4'-Dimethoxybiphenyl

24-nor-5β-cholestane-3α,7α,12α,25-tetrol

(R)-4-[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-(4,5-Dimethoxy-2-nitro-benzyloxy)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

Refernces

• 1、 Qiu, Rongmao,Luo, Guoshun,Li, Xinyu,Zheng, Fan,Li, Haolin,Zhang, Jin,You, Qidong,Xiang, Hua. "Lipid accumulation inhibitory activities of novel isoxazole-based chenodeoxycholic acids: Design, synthesis and preliminary mechanism study". . p. 2879 - 2884. Retrieved 2018.
• 2、 Salunke, Deepak B.,Ravi, Dyavar S.,Pore, Vandana S.,Mitra, Debashis,Hazra, Braja G.. "Amino functionalized novel cholic acid derivatives induce HIV-1 replication and syncytia formation in T cells". . p. 2652 - 2655. Retrieved 2006.
• 3、 Fieser et al.. "-". . p. 3309,3312. Retrieved 1952.
• 4、 Grand,Reichstein. "-". . p. 344,348. Retrieved 1945.
• 5、 Tomkiel, Aneta M.,Kie?czewska, Urszula,Seroka, Barbara,?otowski, Zenon. "Dimeric cholaphanes with disulfide spacers". . p. 252 - 266. Retrieved 2018.
• 6、 Huang, Yanmin,Chen, Sijing,Cui, Jianguo,Gan, Chunfang,Liu, Zhiping,Wei, Yingliang,Song, Huachan. "Synthesis and cytotoxicity of A-homo-lactam derivatives of cholic acid and 7-deoxycholic acid". . p. 690 - 694. Retrieved 2011.
• 7、 Del Amo, Vicente,Bhattarai, Khadga,Nissinen, Maija,Rissanen, Kari,Pérez-Payán, M. Nieves,Davis, Anthony P.. "A short synthesis of methyl 3α, 7α, 12α- triaminocholanoate, the 'triaza-analogue' of methyl cholate". . p. 1319 - 1321. Retrieved 2005.
• 8、 Iida, Takashi,Namegawa, Kazunari,Nakane, Naoya,Iida, Kyoko,Hofmann, Alan Frederick,Omura, Kaoru. "Chemical synthesis of uncommon natural bile acids: The 9α-hydroxy derivatives of chenodeoxycholic and lithocholic acids". . p. 1397 - 1402. Retrieved 2016.
• 9、 Ibrahim-Ouali, Malika,Rocheblave, Luc. "First synthesis of thia steroids from cholic acid". . p. 701 - 709. Retrieved 2010.
• 10、 Zhang, Meng,Levaray, Nicolas,Daniel, Josée R.,Waldron, Karen C.,Zhu. "Cholic acid dimers as invertible amphiphilic pockets: Synthesis, molecular modeling, and inclusion studies". . p. 792 - 798. Retrieved 2017.