475-31-0 Usage
Description
Glycocholic acid, also known as N-Cholylglycine, is a bile salt and a conjugate of cholate and glycine, typically found as the sodium salt. It is a glycine-conjugated form of the primary bile acid cholic acid and plays a crucial role in the emulsification of fats. Glycocholic acid acts as a detergent to solubilize fats for absorption and is itself absorbed. It is characterized by its off-white solid appearance and is involved in various biological processes, including the regulation of gene expression related to bile acid receptors and the modulation of intracellular accumulation and cytotoxicity of certain drugs.
Uses
Used in Pharmaceutical Applications:
Glycocholic acid is used as a cholagogue and choleretic, promoting the flow of bile and aiding in the digestion and absorption of fats. It is particularly useful in the treatment of conditions related to bile flow and fat digestion.
Used in Drug Delivery Systems:
Glycocholic acid is used to increase the intracellular accumulation and cytotoxicity of drugs like epirubicin in Caco-2 cells. It achieves this by decreasing the expression of genes encoding multidrug resistance proteins, such as MDR1, MRP1, and MRP2, when used alone or in combination with epirubicin. This application enhances the efficacy of chemotherapy in cancer treatment.
Used in Research and Diagnostics:
The elevated bile acid composition ratio of glycocholic acid in the bile of patients with cholangiocarcinoma and the increased serum levels of glycocholic acid in patients with hepatocellular carcinoma compared to healthy individuals make it a valuable biomarker for the diagnosis and study of these conditions.
Used in the Study of Bile Acid Receptors:
Glycocholic acid is used to investigate the regulation of gene expression related to bile acid receptors, such as the farnesoid X receptor (FXR), TGR5, and S1PR2, in various cell lines. This research contributes to the understanding of bile acid signaling and its role in metabolic and homeostatic processes.
Purification Methods
Glycocholic acid crystallises from hot water as the sesquihydrate. Dry it at 110o in vacuo. An analytical sample is prepared by suspending the acid (4g) in H2O (400mL) at ~20o, heating to boiling with slow stirring, filtering hot and allowing to cool to ~20o. The acid is filtered off, washed with H2O, dried in air, recrystallised from 5% aqueous EtOH, washed well and dried over P2O5 in a moderate vacuum to constant weight. Recrystallisation from EtOH/EtOAc, and drying, gave the anhydrous acid. [Cortese & Bauman J Am Chem Soc 57 1393 1935, Bergstrom & Norman Acta Chem Scand 7 1126 1953, Beilstein 10 IV 2077.]
Check Digit Verification of cas no
The CAS Registry Mumber 475-31-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,7 and 5 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 475-31:
(5*4)+(4*7)+(3*5)+(2*3)+(1*1)=70
70 % 10 = 0
So 475-31-0 is a valid CAS Registry Number.
InChI:InChI=1/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
475-31-0Relevant articles and documents
SYNTHESIS OF GLYCOCONJUGATE DERIVATIVES OF A BILE ACID
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Paragraph 0086-0087; 0091, (2021/04/10)
Processes for the synthesis and purification of glycoconjugate derivatives of cholic acid are provided herein.
Synthesis, anticancer activities, antimicrobial activities and bioavailability of berberine-bile acid analogues
Li, Qingyong,He, Wuna,Zhang, Li,Zu, Yuangang,Zhu, Qiaochu,Deng, Xiaoqiu,Zhao, Tengfei,Gao, Wenqing,Zhang, Baoyou
scheme or table, p. 573 - 580 (2012/08/08)
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.
An improved procedure for the synthesis of glycine and taurine conjugates of bile acids
Tserng,Hachey,Klein
, p. 404 - 407 (2007/10/06)
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.