Hyocholic acid

Base Information

• Chemical Name: Hyocholic acid
• CAS No.: 547-75-1
• Molecular Formula: C24H40O5
• Molecular Weight: 408.579
• European Community (EC) Number: 208-935-8
• UNII: 2H5H0Q47FL
• DSSTox Substance ID: DTXSID20862167
• Nikkaji Number: J15.782A
• Wikipedia: Hyocholic_acid
• Wikidata: Q27155186
• Metabolomics Workbench ID: 36306
• ChEMBL ID: CHEMBL1908063
• Mol file: 547-75-1.mol

Synonyms:3 alpha,6 alpha,7 beta-trihydroxy-5 beta-cholanoic acid;3,6,7-trihydroxy-5-cholanoic acid;alpha-muricholic acid;beta-muricholic acid;hyocholic acid;muricholic acid;muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer;muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer;muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer;muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer;muricholic acid, (3alpha,5beta,6beta,7beta)-isomer;muricholic acid, sodium salt;omega-muricholic acid;trihydroxy-5 alpha-cholanoic acid

Chemical Property of Hyocholic acid

Chemical Property:

• Melting Point: 162 °C
• Boiling Point: 565.7 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 310 °C
• PSA: 97.99000
• Density: 1.184 g/cm³
• LogP: 3.44870
• Solubility.: Ethanol (Slightly), Methanol (Slightly, Heated)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 408.28757437
• Heavy Atom Count: 29
• Complexity: 637

Purity/Quality:

99%, ^*data from raw suppliers

3α,6α,7α-Trihydroxy-5β-cholanicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2C(C(C4C3(CCC(C4)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H]([C@@H]([C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
• Uses: 3α,6α,7α-Trihydroxy-5β-cholanic Acid is one of the bile acids categorizes under muricholic acid, a group of bile acids found in human urine due to its additional hydroxyl groups. The synthesis of 3α,6 α,7α-Trihydroxy-5β-cholanic Acid was shown to be promoted due to overexpression of cholesterol 7α-hydroxylase enzyme. 3α,6α,7α-Trihydroxy-5β-cholanic Acid is one of the bile acids categorizes under muricholic acid, a group of bile acids found in human urine due to its additional hydroxyl groups. The synthesis of 3α,6α,7α-Trihydroxy-5β-cholanic Acid was shown to be promoted due to overexpression of cholesterol 7α-hydroxylase enzyme.

Technology Process of Hyocholic acid

There total 15 articles about Hyocholic 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: 82.0%

methyl 3α,6α-diacetoxy-7α-hydroxy-5β-cholan-24-oate (127498-19-5) → hyocholic acid (547-75-1)

Guidance literature:

With potassium hydroxide; Heating;

DOI:10.1016/0039-128X(93)90052-O

Reference yield:

7-ketolithocholic methyl ester (10538-59-7) → hyocholic acid (547-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, N,N-dimethylaminopyridine

2: 80 percent / BF₃*Et₂O / acetic acid / 5 h / 55 °C

3: 93 percent / NaBH₄, MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

4: 82 percent / 2M methanolic KOH / Heating

With methanol; dmap; potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/0039-128X(93)90052-O

Reference yield:

methyl 3α-acetoxy-7-oxo-5β-cholan-24-oate (10452-65-0) → hyocholic acid (547-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / BF₃*Et₂O / acetic acid / 5 h / 55 °C

2: 93 percent / NaBH₄, MeOH / CH₂Cl₂ / 0.25 h / Ambient temperature

3: 82 percent / 2M methanolic KOH / Heating

With methanol; potassium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; In dichloromethane; acetic acid;

DOI:10.1016/0039-128X(93)90052-O

upstream raw materials:

3α,6α-dihydroxy-7-oxo-5β-cholan-24-oic acid

methyl 3α,6α-diacetoxy-7α-hydroxy-5β-cholan-24-oate

3α,6α,7α-triacetoxy-5β-cholan-24-oic acid methyl ester

chenodeoxycholic acid methyl ester

Downstream raw materials:

3-oxo-6,7-seco-5β-cholane-6,7,24-trioic acid

3α,6α,7α,24-Tetrahydroxy-24,24-diphenyl-cholan

chenodeoxycholic acid methyl ester

methyl hyodeoxycholate

Refernces