4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

Base Information

• Chemical Name: 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS No.: 81-23-2
• Molecular Formula: C24H34O5
• Molecular Weight: 402.531
• Hs Code.: 2918300000
• NSC Number: 757805
• Wikidata: Q27166907
• ChEMBL ID: CHEMBL3039061
• Mol file: 81-23-2.mol

Synonyms:SR-05000001544;Spectrum_001172;Spectrum2_001375;Spectrum3_001411;BSPBio_003082;KBioSS_001652;SPECTRUM1500907;SPBio_001330;CHEMBL3039061;CHEBI:95125;KBio2_001652;KBio2_004220;KBio2_006788;KBio3_002302;HMS2092O06;Pharmakon1600-01500907;CCG-38851;NSC757805;NSC-757805;NCGC00178307-01;4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid;SBI-0206710.P001;AB01563269_01;SR-05000001544-1;SR-05000001544-2;BRD-A11551002-001-03-8;Q27166907

Chemical Property of 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

Chemical Property:

• Appearance/Colour: white to off-white amorphous powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 238-240 °C
• Refractive Index: 30.5 ° (C=2, Dioxane)
• Boiling Point: 581.5 °C at 760 mmHg
• PKA: pKa 5.12(H2O t = 20 c > CMC) (Uncertain)
• Flash Point: 319.5 °C
• PSA: 88.51000
• Density: 1.172 g/cm³
• LogP: 4.07330
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: ethanol: 10 mg/mL
• Water Solubility.: 65mg/L(30 oC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 402.24062418
• Heavy Atom Count: 29
• Complexity: 756

Purity/Quality:

99% ^*data from raw suppliers

Dehydrocholic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(C(=O)CC3C2C(=O)CC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: CC(CCC(=O)O)[C@H]1CCC2[C@@]1(C(=O)CC3C2C(=O)C[C@H]4[C@@]3(CCC(=O)C4)C)C
• Description: Dehydrocholic acid is a semisynthetic bile acid, which is made by the oxidation of cholic acid by chromic acid. It can increase the output of bile by the liver and the filling of the gallbladder. Dehydrocholic acid aids the digestion of fats and increases absorption of fat soluble vitamins. It is used as a gastrointestinal agent that stimulates the flow of bile into the duodenum (cholagogue) or stimulate the production of bile by the liver (choleretic). It is also used as laxative to relief constipation, diuretic, and a diagnostic aid.
• Uses: Dehydrocholic Acid is a derivative of Cholic Acid (C432600). a choleretic produced by, and isolated from liver cells. antibacterial
• Therapeutic Function: Choleretic, Diuretic, Diagnostic aid

Technology Process of 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid

There total 37 articles about 4-[(5S,10S,13R,17R)-10,13-dimethyl-3,7,12-trioxo-1,2,4,5,6,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pentanoic 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%

cholic acid (81-25-4) → dehydrocholic acid (81-23-2)

Guidance literature:

With sodium hydroxide; sodium perchlorate; sodium chloride; In water; at 25 ℃; for 40h; pH=12; Electrochemical reaction; 50 mA;

DOI:10.1016/S0039-128X(00)00185-9

Reference yield: 100.0%

3,7,12-trihydroxy-5β-cholan-24-oic acid → dehydrocholic acid (81-23-2)

Guidance literature:

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

DOI:10.1021/jo020146b

Reference yield: 94.0%

C27H46O5 → dehydrocholic acid (81-23-2)

Guidance literature:

C₂₇H₄₆O₅; With potassium sulfate; cerous nitrate; at 8 ℃; for 2.33333h; Large scale;

With Tetradecanoic acid 1-methylethyl ester; for 3h; Temperature; Large scale;

upstream raw materials:

cholic acid

(24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate

sodium cholate

water

Downstream raw materials:

methyl 3,7,12-trioxo-5β-cholan-24-oate

3,7,12-trioxo-5β-cholan-24-oic acid ethyl ester

glycodehydrocholic acid

7α,12α-dihydroxy-3-oxocholanoic acid

Refernces

• 1、 Jones,Webb,Smith. "-". . p. 2764. Retrieved 1949.
• 2、 -. "METHODS FOR PREPARING BILE ACIDS". . . Retrieved 2019/02/15.
• 3、 Han, Young Taek,Yun, Hwayoung. "Concise and Efficient Synthesis of 3,7-Dioxo-5β-cholanic Acid via C3,C7-Selective Ketal Protection". . p. 163 - 168. Retrieved 2017/04/26.