3alpha,12beta-Dihydroxy-5beta-cholan-24-oic Acid

Base Information

• Chemical Name: 3alpha,12beta-Dihydroxy-5beta-cholan-24-oic Acid
• CAS No.: 570-62-7
• Molecular Formula: C24H40 O4
• Molecular Weight: 392.579
• DSSTox Substance ID: DTXSID901258025
• Nikkaji Number: J39.832B
• Wikidata: Q27155184
• Metabolomics Workbench ID: 36283
• ChEMBL ID: CHEMBL410872
• Mol file: 570-62-7.mol

Synonyms:570-62-7;Lagodeoxycholic;12-Epideoxycholic acid;3alpha,12beta-Dihydroxy-5beta-cholan-24-oic Acid;12-Epideoxycholate;CCRIS 3992;(4R)-4-[(3R,5R,8R,9S,10S,12R,13R,14S,17R)-3,12-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;LAGODEOXYCHOLATE;3alpha, 12beta-Dihydroxy-5beta-cholanoic acid;3a,12b-Dihydroxycholanoic acid;CHEBI:81242;3|A,12|A-Dihydroxycholanoic acid;(R)-4-((3R,5R,8R,9S,10S,12R,13R,14S,17R)-3,12-Dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid;3alpha,12beta-Dihydroxycholanoic Acid;12-epi-Deoxycholate;12-epi-deoxy-Cholate;12-epi-Deoxycholic acid;12-epi-deoxy-Cholic acid;3a,12b-Dihydroxycholanoate;CHEMBL410872;3a,12b-Dihydroxy-5b-cholanate;SCHEMBL10074117;3a,12b-Dihydroxy-5b-cholanoate;DTXSID901258025;3a,12b-Dihydroxy-5b-cholanic acid;3a,12b-Dihydroxy-5b-cholanoic acid;LMST04010041;AKOS037651135;3a,12b-Dihydroxy-5b-cholan-24-oate;CS-15966;HY-43470;3a,12b-Dihydroxy-5b-cholan-24-oic acid;LS-188152;CS-0080117;3alpha,12beta-dihydroxy-5beta-cholanoic acid;C17646;D72398;Q27155184;(3alpha,5beta,12beta)-3,12-Dihydroxycholan-24-oic acid

Chemical Property of 3alpha,12beta-Dihydroxy-5beta-cholan-24-oic Acid

Chemical Property:

• Melting Point: 178-180 °C
• Boiling Point: 547.1°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 298.8°C
• PSA: 77.76000
• Density: 1.128g/cm³
• LogP: 4.47790
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• 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%min ^*data from raw suppliers

3α,12β-DihydroxycholanoicAcid ^*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(CC3C2CCC4C3(CCC(C4)O)C)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]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: 3α,12β-Dihydroxycholanoic Acid is a bile acid that may decrease of the toxic effects of deoxycholic acid on lipid peroxidn.

Technology Process of 3alpha,12beta-Dihydroxy-5beta-cholan-24-oic Acid

There total 2 articles about 3alpha,12beta-Dihydroxy-5beta-cholan-24-oic 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:

3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester (28050-47-7) → Lagodeoxycholic acid (570-62-7) + Deoxycholic acid (83-44-3)

Guidance literature:

With sodium hydroxide; nickel; Hydrogenation;

DOI:10.1002/hlca.19420250516 DOI:10.1007/BF03018966

Reference yield:

methanol (67-56-1) + 3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester (28050-47-7) → Lagodeoxycholic acid (570-62-7) + Deoxycholic acid (83-44-3)

Guidance literature:

Behandlung des Reaktionsprodukts mit warmer methanol. Kalilauge_.Hydrogenation;

DOI:10.1002/hlca.19420250516 DOI:10.1007/BF03018966

Reference yield: 50.0%

(R)-4-((3R,12S)-3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid (83-44-3,570-62-7,570-63-8,1912-55-6,1912-69-2,2569-02-0,2569-04-2,30635-00-8,84848-09-9) + p-toluenesulfonyl chloride (98-59-9) → 7α-hydroxy-3α-tosyloxy-5β-cholansaeure-24,12α-lacton (88165-73-5)

Guidance literature:

In pyridine; at 5 ℃; for 48h;

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

upstream raw materials:

3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester

methanol

Downstream raw materials:

(R)-4-((3R,5R,8R,9S,10S,12S,13R,17R)-3,12-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid; compound with N-benzyl-N-methyl-2-oxo-propionamide

deoxycholic acid-propiophenone

7α-hydroxy-3α-tosyloxy-5β-cholansaeure-24,12α-lacton

7α,12α-dihydroxy-5β-cholansaeure