360-65-6

Basic information

• Product Name: GLYCODEOXYCHOLIC ACID
• Synonyms: deoxycholylglycine;glycodeoxy-5-beta-cholan-24-oicaci;glykodesoxycholsaeure;n-((3-alpha,5-beta,12-alpha)-3,12-dihydroxy-24-oxocholan-24-yl)-glycine;n-(3-alpha,12-alpha-dihydroxy-5-beta-cholan-24-yl)-glycin;3α,12α-Dihydroxy-5β-cholanoic acid N-(carboxymethyl)amide;N-(3α,12α-Dihydroxy-24-oxocholan-24-yl)glycine ;GLYCODEOXYCHOLIC ACID FREE ACID
• CAS NO: 360-65-6
• Molecular Formula: C₂₆H₄₃NO₅
• Molecular Weight: 467.64
• Mol File: 360-65-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 655.6 °C at 760 mmHg
• Flash Point: 350.3 °C
• Appearance: White solid
• Density: 1.162 g/cm³
• Vapor Pressure: 5.74E-20mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: pKa 3.87±0.06(H2O,t = 25.0±0.1,I=0.00) (Uncertain)
• CAS DataBase Reference: GLYCODEOXYCHOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: GLYCODEOXYCHOLIC ACID(360-65-6)
• EPA Substance Registry System: GLYCODEOXYCHOLIC ACID(360-65-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• RTECS: MB9670000
• F: 10
• Hazardous Substances Data: 360-65-6(Hazardous Substances Data)

Usage

Uses

Glycodeoxycholic Acid is a bile acid that induces severe pancreatitis in rats.

Purification Methods

Glycodeoxycholic acid recrystallises from H2O or aqueous EtOH with 1 mol of H2O and is dried at 100o in vacuo. Its solubility in EtOH is ~5%. [UV: Lindstedt & Sj.vall Acta Chem Scand 11 421 1957.] The Na salt recrystallises from EtOH/Et2O with m 245-250o and [] D23 +41.2o (c 1, H2O) [Wieland Hoppe Seyler's Z Physiol Chem 106 181 1919, Cortese J Am Chem Soc 59 2532 1937]. [Beilstein 10 IV 1611.]

InChI:InChI=1/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1

Upstream product

• 56-40-6 glycine 
• 174069-00-2 2,5-dioxopyrrolidin-1-yl (4R)-4-((3R,10S,12S,13R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 2287-93-6 3α,12α-diformyloxy-5β-cholanoic acid-(24) 
• 86678-83-3 3α,12α-diformyloxy-5β-cholan-24-oic acid chloride 
• 83-44-3 Deoxycholic acid 
• 70779-06-5 ethyl glycodeoxycholate 

Downstream Products

• 68984-81-6 N-(3,12-dioxo-5β-cholanoyl-(24))-glycine 
• 1110779-42-4 C₄₈H₈₀O₄₀*C₂₆H₄₃NO₅ 
• 1345012-02-3 C₂₉H₄₈BrNO₅ 
• 1394077-82-7 C₄₈H₆₃N₂O₉⁽¹⁺⁾*Cl^(1-) 

Relevant articles and documents

BILE ACID-GCPII INHIBITOR CONJUGATES TO TREAT INFLAMMATORY DISEASES

GCPII inhibitors comprising 2-(phosphonomethyl) pentanedioic acid (2-PMPA) conjugated to a bile acid and their use for treating a disease or condition associated with elevated levels of GCPII, including inflammatory bowel disease.

Chemical synthesis, structural analysis, and decomposition of N-nitroso bile acid conjugates

N-nitrosoamides of 7β-hydroxylated bile acid conjugates, particularly of the ursodeoxycholic acid family have been synthesized. The products and synthetic intermediates were fully characterized by the results of high- resolution 1H NMR, FT-1R, FABMS and ESI-MS studies. The compounds, N- nitrosoglycoursodeoxycholic acid (NOGUDCA), N-nitrosoglycoursocholic acid (NOGUCA) and N-nitrosoglycodeoxycholic acid (NOGDCA) decomposed between pH 6 and 9 in aqueous bullet solutions, indicating a t( 1/2 ) of 5-7 h while N- nitrosotauroursodeoxycholic acid (NOTUDCA) indicated a much longer t( 1/2 ) of 15-17 h. These results suggest that the compounds are relatively stable and may enter the enterohepatic circulation. Their decomposition is similar to that of other N-nitrosamides, which generate alkylating agents and thereby act as DNA mutagens.