GLYCODEOXYCHOLIC ACID

Base Information

• Chemical Name: GLYCODEOXYCHOLIC ACID
• CAS No.: 360-65-6
• Deprecated CAS: 125757-76-8,36258-34-1
• Molecular Formula: C26H43NO5
• Molecular Weight: 449.631
• European Community (EC) Number: 623-793-0
• UNII: DS124M0828
• Nikkaji Number: J14.409F
• Wikipedia: Glycodeoxycholic_acid
• Wikidata: Q5572601
• Metabolomics Workbench ID: 36978
• ChEMBL ID: CHEMBL258605
• Mol file: 360-65-6.mol

Synonyms:Glycine,N-(3a,12a-dihydroxy-5b-cholan-24-oyl)- (8CI);Glycodeoxycholic acid(6CI,7CI);5b-Cholan-24-amide,N-(carboxymethyl)-3a,12a-dihydroxy- (8CI);Cholane,glycine deriv.;Deoxycholic acid glycine conjugate;Deoxycholylglycine;Deoxyglycocholic acid;Glycodesoxycholic acid;Glycyldeoxycholic acid;

Chemical Property of GLYCODEOXYCHOLIC ACID

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 5.74E-20mmHg at 25°C
• Melting Point: 184 °C
• Refractive Index: 1.546
• Boiling Point: 655.6 °C at 760 mmHg
• PKA: pKa 3.87±0.06(H2O,t = 25.0±0.1,I=0.00) (Uncertain)
• Flash Point: 350.3 °C
• PSA: 116.09000
• Density: 1.162 g/cm³
• LogP: 3.92070
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 449.31412347
• Heavy Atom Count: 32
• Complexity: 727

Purity/Quality:

99% ^*data from raw suppliers

GlycodeoxycholicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)NCC(=O)O)C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)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]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: Glycodeoxycholic Acid is a bile acid that induces severe pancreatitis in rats.

Technology Process of GLYCODEOXYCHOLIC ACID

There total 10 articles about GLYCODEOXYCHOLIC 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: 83.0%

glycine (56-40-6,18875-39-3,25718-94-9) + 2,5-dioxopyrrolidin-1-yl (4R)-4-((3R,10S,12S,13R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate (174069-00-2) → glycodeoxycholic acid (360-65-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

Reference yield:

Deoxycholic acid (83-44-3) → glycodeoxycholic acid (360-65-6)

Guidance literature:

With 1,4-dioxane; tributyl-amine; chloroformic acid ethyl ester; anschliessendes Behandeln mit Glycin und wss. NaOH;

Reference yield:

glycine (56-40-6,18875-39-3,25718-94-9) → glycodeoxycholic acid (360-65-6)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01291a014

upstream raw materials:

Deoxycholic acid

3α,12α-diformyloxy-5β-cholan-24-oic acid chloride

glycine

ethyl glycodeoxycholate

Downstream raw materials:

C₄₈H₆₃N₂O₉⁽¹⁺⁾*Cl^(1-)

C₂₉H₄₈BrNO₅

C₄₈H₈₀O₄₀*C₂₆H₄₃NO₅

N-(3,12-dioxo-5β-cholanoyl-(24))-glycine

Refernces

• 1、 Li, Qingyong,He, Wuna,Zhang, Li,Zu, Yuangang,Zhu, Qiaochu,Deng, Xiaoqiu,Zhao, Tengfei,Gao, Wenqing,Zhang, Baoyou. "Synthesis, anticancer activities, antimicrobial activities and bioavailability of berberine-bile acid analogues". . p. 573 - 580. Retrieved 2012/08/08.
• 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.