Dehydrolithocholic acid

Base Information

• Chemical Name: Dehydrolithocholic acid
• CAS No.: 1553-56-6
• Molecular Formula: C₂₄H₃₈O₃
• Molecular Weight: 374.564
• European Community (EC) Number: 833-832-5
• UNII: 96JBM35FXF
• Nikkaji Number: J39.835G
• Wikidata: Q27073738
• Pharos Ligand ID: R779VQR8ZL4R
• Metabolomics Workbench ID: 36368
• ChEMBL ID: CHEMBL410893
• Mol file: 1553-56-6.mol

Synonyms:3-keto-5 beta-cholanoic acid;3-oxo-5 beta-cholan-24-oic acid;3-oxocholan-24-oic acid;dehydrolithocholic acid

Chemical Property of Dehydrolithocholic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 140-141 °C
• Refractive Index: 1.52
• Boiling Point: 509.3 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 275.9 °C
• PSA: 54.37000
• Density: 1.069 g/cm³
• LogP: 5.71530
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 374.28209507
• Heavy Atom Count: 27
• Complexity: 613

Purity/Quality:

99% ^*data from raw suppliers

3-Oxo-5β-cholanoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C
• Uses: 3-Oxo-5beta-cholanoic Acid is a steroid compound with pharmacological activity. It is a bile acid. Also used in the preparation of lithocholic acid derivatives used as proteasome regulators. 3-Oxo-5β-cholanoic Acid is a steroid compound with pharmacological activity. It is a bile acid. Also used in the preparation of lithocholic acid derivatives used as proteasome regulators.

Technology Process of Dehydrolithocholic acid

There total 19 articles about Dehydrolithocholic acid 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%

3-hydroxy-5β-cholan-24-oic acid → dehydrolithocholic acid (1553-56-6,19038-19-8,98524-66-4)

Guidance literature:

With jones' reagent; In acetone; for 0.0833333h;

DOI:10.1021/jo020146b

Reference yield: 95.5%

Lithocholic acid (434-13-9) → dehydrolithocholic acid (1553-56-6,19038-19-8,98524-66-4)

Guidance literature:

With sodium hypochlorite; acetic acid; In dichloromethane; at 20 ℃; for 16.5h;

Reference yield: 88.1%

C24H34O3 (59648-73-6) → dehydrolithocholic acid (1553-56-6,19038-19-8,98524-66-4)

Guidance literature:

With piperazine; palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; under 760.051 Torr;

upstream raw materials:

Lithocholic acid

Isolithocholic acid

3,3-(Ethylendioxy)-5β-cholansaeure

sulfuric acid

Downstream raw materials:

Isolithocholic acid

methyl 3-oxo-5β-cholan-24-oate

Lithocholic acid

cholanic acid

Refernces

• 1、 -. "STEROID COMPOUNDS AS TREG MODULATORS AND USES THEREOF". Paragraph 0315. . Retrieved 2020/05/19.
• 2、 -. "Method for preparing acid through oxidating alcohols or aldehydes by oxygen". Paragraph 0051; 0052; 0053; 0054; 0103; 0104; 0105. . Retrieved 2017/09/29.