Glycolithocholic acid

Base Information

• Chemical Name: Glycolithocholic acid
• CAS No.: 474-74-8
• Molecular Formula: C₂₆H₄₃NO₄
• Molecular Weight: 433.632
• UNII: Q53GV75CJG
• DSSTox Substance ID: DTXSID00963828
• Nikkaji Number: J258.541C
• Wikidata: Q27117337
• Metabolomics Workbench ID: 36981
• ChEMBL ID: CHEMBL258818
• Mol file: 474-74-8.mol

Synonyms:3a-Hydroxy-5b-cholanic acid glycine ester;glycolithocholate;glycolithocholic acid;glycolithocholic acid, monosodium salt;lithocholylglycine

Chemical Property of Glycolithocholic acid

Chemical Property:

• Melting Point: 212-214 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 619.7°Cat760mmHg
• PKA: 3.58±0.10(Predicted)
• Flash Point: 328.6°C
• PSA: 86.63000
• Density: 1.112g/cm³
• LogP: 5.01420
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 433.31920885
• Heavy Atom Count: 31
• Complexity: 695

Purity/Quality:

99%min ^*data from raw suppliers

Lithocholylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)NCC(=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)C
• Description: Glycolithocholic acid is a glycine-conjugated form of the secondary bile acid lithocholic acid . It is increased in the liver of mice fed a diet supplemented with ursodeoxycholic acid . Glycolithocholic acid levels are decreased in the plasma following subcutaneous administration of PEG-obestatin(Cys10, Cys13), a modified peptide hormone, in lean or diet-induced obese mice. Serum glycolithocholic acid levels increase with age in children.
• Uses: A metabolite in human hepatic bile. A lithocholic acid analog that inhibit sialyltransferase. A metabolite in human hepatic bile.

Technology Process of Glycolithocholic acid

There total 5 articles about Glycolithocholic 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: 95.0%

methyl N-(3α-hydroxy-5β-cholan-24-oyl)glycinate (69320-20-3) → glycolithocholic acid (13164-19-7,69351-31-1,78479-09-1,139894-84-1,474-74-8)

Guidance literature:

methyl N-(3α-hydroxy-5β-cholan-24-oyl)glycinate; With sodium hydroxide; In ethanol; at 20 ℃; for 1h;

With hydrogenchloride; In water;

DOI:10.1021/jm301890k

Reference yield: 69.0%

C30H51NO4 (881179-18-6) → glycolithocholic acid (13164-19-7,69351-31-1,78479-09-1,139894-84-1,474-74-8)

Guidance literature:

With water; trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1039/b514915k

Reference yield:

Lithocholic acid (434-13-9) → glycolithocholic acid (13164-19-7,69351-31-1,78479-09-1,139894-84-1,474-74-8)

Guidance literature:

With 1,4-dioxane; tributyl-amine; chloroformic acid ethyl ester; anschliessend Behandeln mit Natriumglycinat in H₂O;

upstream raw materials:

Lithocholic acid

C₃₀H₅₁NO₄

methyl N-(3α-hydroxy-5β-cholan-24-oyl)glycinate

Refernces

• 1、 Incerti, Matteo,Tognolini, Massimiliano,Russo, Simonetta,Pala, Daniele,Giorgio, Carmine,Hassan-Mohamed, Iftiin,Noberini, Roberta,Pasquale, Elena B.,Vicini, Paola,Piersanti, Silvia,Rivara, Silvia,Barocelli, Elisabetta,Mor, Marco,Lodola, Alessio. "Amino acid conjugates of lithocholic acid as antagonists of the EphA2 receptor". . p. 2936 - 2947. Retrieved 2013/05/22.
• 2、 Tserng,Hachey,Klein. "An improved procedure for the synthesis of glycine and taurine conjugates of bile acids". . p. 404 - 407. Retrieved 2007/10/06.