Lithocholate 3-O-glucuronide

Base Information

• Chemical Name: Lithocholate 3-O-glucuronide
• CAS No.: 75239-91-7
• Molecular Formula: C₃₀H₄₈O₉
• Molecular Weight: 552.706
• Mol file: 75239-91-7.mol

Synonyms:lithocholate 3-O-beta-D-glucuronide;lithocholate 3-O-glucuronide;lithocholic acid glucuronide

Chemical Property of Lithocholate 3-O-glucuronide

Chemical Property:

• Vapor Pressure: 2.25E-24mmHg at 25°C
• Boiling Point: 726.6°C at 760 mmHg
• PKA: 2.82±0.70(Predicted)
• Flash Point: 231.6°C
• PSA: 153.75000
• Density: 1.29g/cm³
• LogP: 3.42360
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 552.32983310
• Heavy Atom Count: 39
• Complexity: 926

Purity/Quality:

98% ^*data from raw suppliers

LithocholicAcid3-O-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C)C
• Uses: Lithocholic Acid 3-O-Glucuronide is an impurity of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

Technology Process of Lithocholate 3-O-glucuronide

There total 6 articles about Lithocholate 3-O-glucuronide 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%

lithocholic acid methyl ester O-β-D-glucuronide (59274-61-2,75672-11-6,83701-10-4,101900-62-3) → lithocholic acid O-β-D-glucuronide (75239-91-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 4h; pH=14;

DOI:10.1016/j.ejmech.2016.01.002

Reference yield:

benzyl 3α-hydroxy-5β-cholan-24-oate-3-β-D-glucuronide methyl ester triacetate → lithocholic acid O-β-D-glucuronide (75239-91-7)

Guidance literature:

With water; sodium hydroxide; In toluene; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2017.12.034

Reference yield:

Lithocholic acid (434-13-9) → lithocholic acid O-β-D-glucuronide (75239-91-7)

Guidance literature:

Multi-step reaction with 3 steps

1: caesium carbonate / acetonitrile / Reflux

2: Fetizon's reagent / toluene / 38 °C / 5171.62 Torr / Molecular sieve

3: sodium hydroxide; water / toluene / 1 h / 20 °C

With water; caesium carbonate; sodium hydroxide; In toluene; acetonitrile; 2: |Koenigs-Knorr Glycosidation;

DOI:10.1016/j.ejmech.2017.12.034

upstream raw materials:

methyl lithocholate

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

lithocholic acid methyl ester O-β-D-glucuronide

Lithocholic acid