Dehydrodeoxycholic acid

Base Information

• Chemical Name: Dehydrodeoxycholic acid
• CAS No.: 2958-05-6
• Molecular Formula: C24H36 O4
• Molecular Weight: 388.547
• European Community (EC) Number: 220-982-6
• NSC Number: 60789
• UNII: 45UU3FP8KW
• DSSTox Substance ID: DTXSID70183753
• Nikkaji Number: J39.833K
• Wikidata: Q63395899
• Metabolomics Workbench ID: 36379
• ChEMBL ID: CHEMBL3391716
• Mol file: 2958-05-6.mol

Synonyms:3,12-dioxo-5 beta-cholan-24-oic acid;dehydrodeoxycholic acid;dioxo-DCA

Chemical Property of Dehydrodeoxycholic acid

Chemical Property:

• Melting Point: 176 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 544.7°Cat760mmHg
• PKA: 4.74±0.10(Predicted)
• Flash Point: 297.3°C
• PSA: 71.44000
• Density: 1.12g/cm³
• LogP: 4.89430
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 388.26135963
• Heavy Atom Count: 28
• Complexity: 684

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

3,12-Diketo-5β-cholanoicAcid ^*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(=O)CC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(C(=O)C[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC(=O)C4)C)C
• Uses: 3,12-Diketo-5β-cholanoic Acid and other oxo derivatives of cholic, deoxycholic and chenodeoxycholic acids have been studied for their hydrophobicity and hemolytic potential.

Technology Process of Dehydrodeoxycholic acid

There total 18 articles about Dehydrodeoxycholic 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%

3,12-dihydroxy-5β-cholan-24-oic acid → 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Guidance literature:

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

DOI:10.1021/jo020146b

Reference yield: 98.0%

Deoxycholic acid (83-44-3) → 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; acetone; In water; at 20 ℃;

DOI:10.1002/ejoc.200600972

Reference yield: 61.0%

sodium cholate (302-95-4) → 3-keto-12α-hydroxy-5β-cholan-24-oic acid (4185-01-7) + 3,12-dioxo-7-deoxycholic acid (2958-05-6)

Guidance literature:

With Rhodococcus erythropolis ECS₂₅; In water; at 28 ℃; for 24h; Microbiological reaction;

DOI:10.1002/cbdv.201500300

upstream raw materials:

1-methyl-4-nitrosobenzene

Deoxycholic acid

12-oxolithocholic acid

3β-hydroxy-12-oxo-5β-cholanoic acid-(24)

Downstream raw materials:

12-oxolithocholic acid

3β-hydroxy-12-oxo-5β-cholanoic acid-(24)

3,4;11,12-diseco-5β-cholanepentaoic acid-(3.4.11.12.24)

cholanic acid

Refernces

• 1、 Ishida, Hitoshi,Miyamoto, Hidekazu,Kajino, Takako,Nakayasu, Hidetoshi,Nukaya, Haruo,Tsuji, Kuniro. "Study on the bile salt from megamouth shark. I. The structures of a new bile alcohol, 7-deoxyscymnol, and its new sodium sulfates". . p. 1289 - 1292. Retrieved 1996.
• 2、 Fantin, Giancarlo,Ferrarini, Sabina,Medici, Alessandro,Pedrini, Paola,Poli, Silvia. "Regioselective microbial oxidation of bile acids". . p. 1937 - 1942. Retrieved 1998.
• 3、 Verzele, Dieter,Madder, Annemieke. "Short synthesis of orthogonally protected 3α,12α-diamino- 5β-cholan-24-oic acid, a dipodal steroid scaffold for combinatorial chemistry". . p. 1793 - 1797. Retrieved 2007.
• 4、 Costa, Stefania,Maldonado Rodriguez, Maria Elena,Rugiero, Irene,De Bastiani, Morena,Medici, Alessandro,Tamburini, Elena,Pedrini, Paola. "Biotransformations of Bile Acids with Bacteria from Cayambe Slaughterhouse (Ecuador): Synthesis of Bendigoles". . p. 969 - 975. Retrieved 2016/09/09.