75239-91-7

Basic information

• Product Name: (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid
• Synonyms: (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid;Lithocholate 3-O-glucuronide
• CAS NO: 75239-91-7
• Molecular Formula: C30H48O9
• Molecular Weight: 552.7
• Mol File: 75239-91-7.mol

Chemical Properties

• Boiling Point: 726.6°C at 760 mmHg
• Flash Point: 231.6°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 2.25E-24mmHg at 25°C
• Refractive Index: 1.581
• PKA: 2.82±0.70(Predicted)
• CAS DataBase Reference: (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid(75239-91-7)
• EPA Substance Registry System: (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid(75239-91-7)

Safety Data

• Hazardous Substances Data: 75239-91-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid is used as an impurity in the production of Lithocholic Acid (L469180), a cholic acid derivative that acts as a TGR5 modulator. (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid is essential for the development and optimization of pharmaceuticals targeting TGR5 receptors, which play a role in various physiological processes, including bile acid metabolism and glucose homeostasis.
Used in Research and Development:
In the field of research, (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid can be utilized as a reference compound for studying the properties and interactions of similar molecules. Its unique structure may provide insights into the design and synthesis of new compounds with potential applications in drug development, material science, or other areas of research.
Used in Quality Control and Analysis:
As an impurity of Lithocholic Acid, (3a,5b)-23-carboxy-24-norcholan-3-yl b-D-glucopyranosiduronic acid can be used in quality control processes to ensure the purity and efficacy of pharmaceutical products containing Lithocholic Acid. Analytical techniques, such as high-performance liquid chromatography (HPLC) or mass spectrometry, can be employed to detect and quantify the presence of this impurity in the final product.

InChI:InChI=1/C30H48O9/c1-15(4-9-22(31)32)19-7-8-20-18-6-5-16-14-17(10-12-29(16,2)21(18)11-13-30(19,20)3)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h15-21,23-26,28,33-35H,4-14H2,1-3H3,(H,31,32)(H,36,37)/t15-,16-,17+,18+,19-,20+,21+,23+,24+,25-,26+,28-,29+,30-/m1/s1

Upstream product

• 434-13-9 Lithocholic acid 
• 6112-83-0 benzyl (R)-4-((3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 59274-61-2 lithocholic acid methyl ester O-β-D-glucuronide 
• 1249-75-8 methyl lithocholate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Relevant articles and documents

Synthesis and evaluation of Vitamin D receptor-mediated activities of cholesterol and Vitamin D metabolites

A systematic study with phase 1 and phase 2 metabolites of cholesterol and Vitamin D was conducted to determine whether their biological activity is mediated by the Vitamin D receptor (VDR). The investigation necessitated the development of novel synthetic routes for lithocholic acid (LCA) glucuronides (Gluc). Biochemical and cell-based assays were used to demonstrate that hydroxylated LCA analogs were not able to bind VDR. This excludes VDR from mediating their biological and pharmacological activities. Among the synthesized LCA conjugates a novel VDR agonist was identified. LCA Gluc II increased the expression of CYP24A1 in DU145 cancer cells especially in the presence of the endogenous VDR ligand 1,25(OH)2D3.Furthermore, the methyl ester of LCA was identified as novel VDR antagonist. For the first time, we showed that calcitroic acid, the assumed inactive final metabolite of Vitamin D, was able to activate VDR-mediated transcription to a higher magnitude than bile acid LCA. Due to a higher metabolic stability in comparison to Vitamin D, a very low toxicity, and high concentration in bile and intestine, calcitroic acid is likely to be an important mediator of the protective Vitamin D properties against colon cancer.

Synthesis, physicochemical properties, and biological activity of bile acids 3-glucuronides: Novel insights into bile acid signalling and detoxification

Glucuronidation is considered an important detoxification pathway of bile acids especially in cholestatic conditions. Glucuronides are less toxic than the parent free forms and are more easily excreted in urine. However, the pathophysiological significanc