360-65-6

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

• 83-44-3 Deoxycholic acid 
• 70779-06-5 ethyl glycodeoxycholate 
• 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 
• 56-40-6 glycine 
• 2287-93-6 3α,12α-diformyloxy-5β-cholanoic acid-(24) 
• 86678-83-3 3α,12α-diformyloxy-5β-cholan-24-oic acid chloride 

Downstream Products

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

Relevant academic research and scientific papers

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.

Synthesis, anticancer activities, antimicrobial activities and bioavailability of berberine-bile acid analogues

Fifteen berberine-bile acid analogues were synthesized. Anticancer activities of these analogues compared with berberine (BBR) were evaluated in vitro; among the analogues, A4, B4, and B5 had higher cytotoxicity than that of BBR. Most of the analogues showed higher antimicrobial activity against Staphylococcus aureus ATCC 25923 and Staphylococcus albus ATCC 8799 than that of BBR, but Bacillus subtilis AS 1.398 and Escherichia coli ATCC 31343 were not sensitive to all of the analogues. A4 and B4 were stable in the serum stability assay. B4 showed promising oral bioavailability in mice.

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.

An improved procedure for the synthesis of glycine and taurine conjugates of bile acids

Glycine and taurine conjugates of 5β cholanic acids have been synthesized using improved procedures based on the peptide coupling reagent, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The conjugates are obtained in chromatographically pure form in yields higher than 90%. The use of this procedure in the large scale preparation of choly[1,2 13C2]glycine is described.