N-Choloylglycine

Base Information

• Chemical Name: N-Choloylglycine
• CAS No.: 475-31-0
• Molecular Formula: C26H43NO6
• Molecular Weight: 465.631
• Wikidata: Q27104084
• Mol file: 475-31-0.mol

Synonyms:N-Choloylglycine;C26H43NO6;C26-H43-N-O6;Glycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)-;N-[(3alpha,5-beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine;CHEMBL2074587;CHEBI:29746;BDBM50420252;DB02691;Q27104084;N-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-oyl)glycinate

Chemical Property of N-Choloylglycine

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 3.7E-22mmHg at 25°C
• Melting Point: 128 °C
• Refractive Index: 1.56
• Boiling Point: 692.042 °C at 760 mmHg
• PKA: 4.4(at 25℃)
• Flash Point: 372.334 °C
• PSA: 127.09000
• Density: 1.213 g/cm³
• LogP: 2.95580
• Storage Temp.: Refrigerator
• Solubility.: methanol: 0.1 g/mL, clear, colorless
• Water Solubility.: 329.9mg/L(20 oC)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 464.30121306
• Heavy Atom Count: 33
• Complexity: 754

Purity/Quality:

99% ^*data from raw suppliers

Glycocholic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CCC(=O)NCC(=O)[O-])C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
• Isomeric SMILES: C[C@H](CCC(=O)NCC(=O)[O-])[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(CC[C@H](C4)O)C)O)O)C
• Description: N-Cholylglycine. Bile salt, conjugate of cholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as a cholagogue and choleretic. Glycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid and has roles in the emulsification of fats. It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml. Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin. It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases. Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals.

Technology Process of N-Choloylglycine

There total 12 articles about N-Choloylglycine 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: 92.3%

glycocholic acid ethyl ester (517904-33-5,94006-05-0) → glycocholic acid (475-31-0)

Guidance literature:

glycocholic acid ethyl ester; With water; sodium hydroxide; at 20 - 28 ℃;

With hydrogenchloride; In water; pH=7 - 7.5;

Reference yield: 78.3%

cholic acid (81-25-4) + glycine ethyl ester hydrochloride (623-33-6) → glycocholic acid (475-31-0)

Guidance literature:

cholic acid; With triethylamine; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

glycine ethyl ester hydrochloride; With pivaloyl chloride; In tetrahydrofuran; water; at 0 - 10 ℃; Reagent/catalyst;

Reference yield:

glycocholic acid methyl ester → glycocholic acid (475-31-0)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; water; at 35 - 40 ℃; for 10h;

upstream raw materials:

cholic acid

chloroformic acid ethyl ester

3α,7α,12α-trihydroxy-5β-cholanoyl-(24)-azide

glycine

Downstream raw materials:

N-nitrosoglycocholic acid

carbon dioxide

(3α,5β,7α,12α)3,7,12-trihydroxy-cholan-24-amide

oxalic acid

Refernces

• 1、 -. "Cholic acid derivative with antibacterial activity and pharmaceutical composition thereof". . . Retrieved 2020/03/25.
• 2、 -. "METHOD FOR THE SYNTHESIS OF GLYCOCHOLIC ACID". Page/Page column 6. . Retrieved 2010/11/18.