Isodeoxycholic acid

Base Information

• Chemical Name: Isodeoxycholic acid
• CAS No.: 566-17-6
• Molecular Formula: C₂₄H₄₀O₄
• Molecular Weight: 392.579
• DSSTox Substance ID: DTXSID701315756
• Nikkaji Number: J363.678J
• Wikidata: Q27155197
• Metabolomics Workbench ID: 36291
• Mol file: 566-17-6.mol

Synonyms:Isodeoxycholic acid;566-17-6;5-beta-cholanic acid-7-alpha, 12-alpha-diol;7alpha,12alpha-Dihydroxy-5beta-cholan-24-oic Acid;7alpha,12alpha-Dihydroxy-5beta-cholanic acid;(4R)-4-[(5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid;3-Deoxycholic acid;Cholan-24-oic acid, 7,12-dihydroxy-, (5beta,7alpha,12alpha)-;7a,12a-Dihydroxycholanoate;SCHEMBL1654634;7a,12a-Dihydroxycholanoic acid;7a,12a-Dihydroxy-5b-cholanoate;CHEBI:81256;DTXSID701315756;7a,12a-Dihydroxy-5b-cholanic acid;7a,12a-Dihydroxy-5b-cholanoic acid;LMST04010049;AKOS040755350;7a,12a-dihydroxy-5b-Cholan-24-oate;7alpha,12alpha-Dihydroxycholanoic acid;5beta-cholanic acid-7alpha,12alpha-diol;7a,12a-dihydroxy-5b-Cholan-24-oic acid;7alpha,12alpha-Dihydroxy-5beta-cholan-24-oate;C17661;Q27155197

Chemical Property of Isodeoxycholic acid

Chemical Property:

• Vapor Pressure: 2.98E-14mmHg at 25°C
• Melting Point: 210 °C
• Boiling Point: 547.1 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 298.8 °C
• PSA: 77.76000
• Density: 1.128 g/cm³
• LogP: 4.47790
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 392.29265975
• Heavy Atom Count: 28
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

Isodeoxycholic 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(C(CC3C2C(CC4C3(CCCC4)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CCCC4)C)O)O)C
• Uses: Isodeoxycholic Acid is used for comprehensive bile acid profiling in hereditary intrahepatic cholestasis.

Technology Process of Isodeoxycholic acid

There total 24 articles about Isodeoxycholic 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: 90.0%

7α-hydroxy-5β-cholansaeure-24,12α-lacton (88165-75-7) → 7α,12α-dihydroxy-5β-cholansaeure (566-17-6,15073-89-9,30627-74-8,84413-80-9,84413-81-0,84413-82-1,105227-29-0,105227-30-3,105227-31-4)

Guidance literature:

With potassium hydroxide; In methanol; for 4h;

DOI:10.1016/S0040-4020(01)82452-2

Reference yield:

7α,12α-dihydroxy-3-oxocholanoic acid (2304-89-4) → 3-deoxycholic acid (566-17-6)

Guidance literature:

With 85percent KOH; 80percent hydrazinium hydroxide; In 2-methoxy-ethanol; water; at 110 - 135 ℃; for 12h;

DOI:10.1021/jo020146b

Reference yield:

methyl 3-keto-7,12-diacetylcholate (4947-65-3) → 3-deoxycholic acid (566-17-6)

Guidance literature:

With sodium ethanolate; hydrazine hydrate; at 200 ℃;

upstream raw materials:

7β-hydroxy-12-oxo-5α-cholanic acid

methyl 7β-hydoxy-12-oxo-5α-cholanate

7,12-dioxo-5α-cholan-24-oic acid methyl ester

7,12-dioxo-chola-3,5-dien-24-oic acid methyl ester

Downstream raw materials:

7β,12α-dihydroxy-5β-cholan-24-oic acid

Refernces

• 1、 Bortolini, Olga,Fantin, Giancarlo,Fogagnolo, Marco,Forlani, Roberto,Maietti, Silvia,Pedrini, Paola. "Improved enantioselectivity in the epoxidation of cinnamic acid derivatives with dioxiranes from keto bile acids". . p. 5802 - 5806. Retrieved 2007/10/03.
• 2、 Wolf,Foster,Blickenstaff. "Intramolecular catalysis. VI. Selectivity in 7 ,12 -dihydroxy steroids and enhancement of 12 -hydroxyl reactivity by substituents at carbon 3.". . p. 1276 - 1279. Retrieved 2007/10/13.