Methyl 7a,12a-dihydroxy-5b-chol-3-enoate

Base Information

• Chemical Name: Methyl 7a,12a-dihydroxy-5b-chol-3-enoate
• CAS No.: 77731-11-4
• Molecular Formula: C25H40O4
• Molecular Weight: 404.58
• DSSTox Substance ID: DTXSID80561088
• Wikidata: Q72466562
• Mol file: 77731-11-4.mol

Synonyms:Methyl 7a,12a-dihydroxy-5b-chol-3-enoate;77731-11-4;methyl (4R)-4-[(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-2,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate;(5beta,7alpha,12alpha)-7,12-Dihydroxychol-3-en-24-oic acid methyl ester;DTXSID80561088;A865166

Chemical Property of Methyl 7a,12a-dihydroxy-5b-chol-3-enoate

Chemical Property:

• Melting Point: 136-137 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• Boiling Point: 506.9±50.0 °C(Predicted)
• PKA: 14.69±0.70(Predicted)
• PSA: 66.76000
• Density: 1.103
• LogP: 4.34230
• Storage Temp.: 2-8°C
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 404.29265975
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

97% ^*data from raw suppliers

METHYL-7ALPHA,12ALPHA-DIHYDROXY-5BETA-CHOL-3-ENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)OC)C1CCC2C1(C(CC3C2C(CC4C3(CCC=C4)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)OC)[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(CCC=C4)C)O)O)C

Technology Process of Methyl 7a,12a-dihydroxy-5b-chol-3-enoate

There total 8 articles about Methyl 7a,12a-dihydroxy-5b-chol-3-enoate 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: 73.0%

7α,12α-dihydroxy-3α-(toluene-sulfonyl-(4)-oxy)-5β-cholanoic acid-(24)-methyl ester (28192-77-0) → methyl 7α,12α-dihydroxy-5β-chol-3-enoate (77731-11-4)

Guidance literature:

With 2,6-dimethylpyridine; at 130 ℃; for 2h;

DOI:10.1021/jacs.1c11902

Reference yield: 21.0%

7α,12α-Dihydroxy-3α-(p-tolylsulfonyloxy)-5β-cholansaeure-methylester (28192-77-0,110655-79-3) → 7α,12α-Dihydroxychol-4-ensaeure-methylester (77731-18-1) + 3α,7α-Epoxy-12α-hydroxy-5β-cholansaeure-methylester + 7α,12α-Dihydroxy-5β-chol-3-ensaeure-methylester (77731-11-4) + 7α,12α-Dihydroxy-5β-chol-2-ensaeure-methylester (77731-10-3)

Guidance literature:

With aluminum oxide; In benzene; Further byproducts given. Yields of byproduct given; Heating;

DOI:10.1002/ardp.19813140205

Reference yield: 14.0%

7α,12α-dihydroxy-3α-(toluene-sulfonyl-(4)-oxy)-5β-cholanoic acid-(24)-methyl ester (28192-77-0) → methyl 7α,12α-dihydroxy-5β-chol-3-enoate (77731-11-4) + methyl 7α,12α-dihydroxy-5β-chol-2-enoate (77731-10-3)

Guidance literature:

With 2,6-dimethylpyridine; for 1h; Heating;

DOI:10.1248/cpb.37.3323

upstream raw materials:

7α,12α-dihydroxy-3α-(toluene-sulfonyl-(4)-oxy)-5β-cholanoic acid-(24)-methyl ester

methyl cholate

7α,12α-Dihydroxy-3α-(p-tolylsulfonyloxy)-5β-cholansaeure-methylester

deoxycholic acid

Downstream raw materials:

3β,4β,7α,12α-tetrahydroxy-5β-cholanoic acid

3α,4β,7α,12α-tetrahydroxy-5β-cholanoic acid