Methyl 3-hydroxychol-5-en-24-oate

Base Information

• Chemical Name: Methyl 3-hydroxychol-5-en-24-oate
• CAS No.: 20231-57-6
• Molecular Formula: C25H40 O3
• Molecular Weight: 388.591
• NSC Number: 84140
• DSSTox Substance ID: DTXSID80942338
• Mol file: 20231-57-6.mol

Synonyms:methyl 3-hydroxychol-5-en-24-oate;NSC84140;Oprea1_298081;DTXSID80942338;STL372742;AKOS040894256;3.beta.-Hydroxy-5-cholenic acid, methyl ester;5-Cholenicacid-3beta-olmethylester,3-methylether;Chol-5-en-24-oic acid, methyl ester, (3.beta.)-

Chemical Property of Methyl 3-hydroxychol-5-en-24-oate

Chemical Property:

• Vapor Pressure: 2.13E-11mmHg at 25°C
• Boiling Point: 484°C at 760 mmHg
• Flash Point: 183.1°C
• PSA: 46.53000
• Density: 1.07g/cm³
• LogP: 5.51560
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 388.29774513
• Heavy Atom Count: 28
• Complexity: 640

Purity/Quality:

97% ^*data from raw suppliers

(R)-Methyl4-((3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Uses: 3β-Hydroxychol-5-enoic Acid Methyl Ester is a derivative of 5-Cholenic acid-3β-ol, an selective inhibition of cyclic AMP-dependent protein kinase. 3β-Hydroxychol-5-enoic Acid Methyl Ester is a reactant used in the preparation of cholenoic acid based bile acids present in human biological fluids.

Technology Process of Methyl 3-hydroxychol-5-en-24-oate

There total 37 articles about Methyl 3-hydroxychol-5-en-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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3β-hydroxy-5-cholenoic acid (5255-17-4) → methyl 5-cholenoate (20231-57-6)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 20 ℃; for 0.666667h;

DOI:10.1023/A:1015720707433

Reference yield: 96.7%

methyl 3α,7β-ditosyloxy-5β-cholan-24-oate → methyl 5-cholenoate (20231-57-6)

Guidance literature:

With potassium acetate; In water; N,N-dimethyl-formamide; at 105 ℃; for 7h;

Reference yield: 96.0%

methyl 3α,6α-ditosyloxy-5β-cholan-24-oate (1184-20-9) → methyl 5-cholenoate (20231-57-6)

Guidance literature:

With potassium acetate; In water; N,N-dimethyl-formamide; for 24h; Heating;

DOI:10.1016/j.steroids.2005.07.008

upstream raw materials:

methanol

3β-hydroxy-5-cholenoic acid

methyl iodide

diazomethane

Downstream raw materials:

methyl 3β-hydroxy-5α-cholan-24-oate

3β-acetoxy-24,24-dimethyl-choladiene-(5,23)

methyl 3-oxo-4-cholenolate

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol

Refernces

• 1、 Khripach,Zhabinskii,Konstantinova,Khripach,Antonchick. "Synthesis of 24-functionalized oxysterols". . p. 257 - 261. Retrieved 2002.
• 2、 Chen, Wang,Hu, Daihua,Feng, Zili,Liu, Zhaopeng. "An effective synthesis of ursodeoxycholic acid from dehydroepiandrosterone". supporting information. . Retrieved 2021/06/16.
• 3、 Jin, Can,Wang, Yulei,Sun, Bin,Su, Weike. "A concise synthesis of 25-Hydroxycholesterol from hyodesoxycholic Acid". . p. 96 - 99. Retrieved 2018/03/21.