5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester

Base Information

• Chemical Name: 5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester
• CAS No.: 14773-00-3
• Molecular Formula: C25H40O4
• Molecular Weight: 404.59
• DSSTox Substance ID: DTXSID70471884
• Nikkaji Number: J128.873C
• Wikidata: Q82300575
• Mol file: 14773-00-3.mol

Synonyms:14773-00-3;Methyl 7|A-Hydroxy-3-ketocholanoate;5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester;methyl (4R)-4-[(5R,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoate;5.beta.-Cholan-24-oic acid, 7.alpha.-hydroxy-3-oxo-, methyl ester;Cholan-24-oic acid, 7-hydroxy-3-oxo-, methyl ester, (5.beta.,7.alpha.)-;SCHEMBL22731245;DTXSID70471884;XHRLTYUHWGHDCJ-WZAAVQHPSA-N;Methyl-3-keto-7-hydroxy-5-cholanoate;Methyl 7alpha-Hydroxy-3-ketocholanoate;Methyl 5-.beta.-cholan-7-.alpha.-ol-3-one-24-oate;Methyl 7-hydroxy-3-oxocholan-24-oate, (5.beta.,7.alpha.)-

Chemical Property of 5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester

Chemical Property:

• Melting Point: 128-129 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 505.7±25.0 °C(Predicted)
• PKA: 14.80±0.70(Predicted)
• Density: 1.085±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 404.29265975
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl7α-Hydroxy-3-ketocholanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2C(CC4C3(CCC(=O)C4)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCC(=O)C4)C)O)C
• Uses: 3-Oxo-7α-hydroxy-5β-cholan-24-oic acid methyl ester, steroidal fused pyrazoles useful as bile acid transporters.

Technology Process of 5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester

There total 15 articles about 5beta-Cholan-24-oic acid, 7alpha-hydroxy-3-oxo-, methyl ester 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: 98.0%

chenodeoxycholic acid methyl ester (3057-04-3) → methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3)

Guidance literature:

With oxygen; platinum; In ethyl acetate; for 100h; under 760 Torr; Ambient temperature;

DOI:10.1016/S0040-4020(01)86327-4

Reference yield: 91.0%

TMSCH2N2 + chenodeoxycholic acid (474-25-9) → methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3)

Guidance literature:

In methanol; diethyl ether; toluene; at 20 ℃; for 0.333333h;

DOI:10.1002/anie.201307465

Reference yield: 36.0%

chenodeoxycholic acid methyl ester (3057-04-3) → methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate (14773-00-3) + 7-ketolithocholic methyl ester (10538-59-7) + methyl 3,7-dioxocholan-24-oate (7753-72-2)

Guidance literature:

With dimethoxydioxirane*H₂O; In acetone; at 0 - 5 ℃; for 16h;

DOI:10.1016/S0040-4039(99)00834-5

upstream raw materials:

diazomethane

3-keto-7α-formyloxy-5β-cholan-24-oic acid

chenodeoxycholic acid methyl ester

(R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

Downstream raw materials:

14-methyl-3-oxo-5β-chol-7-enoate

(R)-4-((5R,7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

(R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

methyl 7α-methoxymethyloxy-3-oxo-5β-cholan-24-oate

Refernces

• 1、 Kagan,Jacques. "-". . p. 699,703. Retrieved 1957.
• 2、 Judkins, Joshua C.,Mahanti, Parag,Hoffman, Jacob B.,Yim, Isaiah,Antebi, Adam,Schroeder, Frank C.. "A photocleavable masked nuclear-receptor ligand enables temporal control of C.elegans development". supporting information. p. 2110 - 2113. Retrieved 2014/03/21.