81-25-4
81-25-4
Chemical Structure
Cholic acid
- CAS No.: 81-25-4
- Formula:C24H40O5
- Molecular Weight:408.57
IUPAC Name: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
InChIKey: BHQCQFFYRZLCQQ-OELDTZBJSA-N
SMILES: C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C
Biological Activity: Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active[1][2].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Cholic acid | 99.80% | Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active. | ||||||||||||||||||||
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Cholic acid (Standard) | 99.90% | Cholic acid (Standard) is the analytical standard of Cholic acid. This product is intended for research and analytical applications. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid is orally active. | ||||||||||||||||||||
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Cholic acid-d4 | 99.91% | Cholic acid-d4 is the deuterium labeled Cholic acid. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. | ||||||||||||||||||||
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Cholic acid-d5 | 99.80% | Cholic acid-d5 is the deuterium labeled Cholic acid. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. | ||||||||||||||||||||
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Cholic acid-13C | 99.17% | Cholic acid-13C is the 13C-labeled Cholic acid. Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. | ||||||||||||||||||||
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Methyl cholate | 99.81% | Methyl cholate is a bile acid analog and a specific inhibitor of TcdB toxin from Clostridioides difficile. Methyl cholate exerts a stronger selective inhibitory effect on TcdB than on TcdA. Methyl cholate induces conformational stabilization by binding to a unique site of TcdB, thereby blocking the binding of the toxin to host receptors and its self-processing process. Methyl cholate effectively protects human fibroblasts from TcdB-induced cytopathic effects. Methyl cholate exhibits dose-dependent anti-hepatic fibrosis activity in both cellular and zebrafish models, and significantly reduces the expression levels of α-SMA and COL-I. Methyl cholate is suitable for in-depth research in the fields of Clostridioides difficile infection and hepatic fibrosis. | ||||||||||||||||||||
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Methyl cholate (Standard) | ≥98% | Methyl cholate (Standard) is the analytical standard of Methyl cholate. This product is intended for research and analytical applications. Methyl cholate is a bile acid analog and a specific inhibitor of TcdB toxin from Clostridioides difficile. Methyl cholate exerts a stronger selective inhibitory effect on TcdB than on TcdA. Methyl cholate induces conformational stabilization by binding to a unique site of TcdB, thereby blocking the binding of the toxin to host receptors and its self-processing process. Methyl cholate effectively protects human fibroblasts from TcdB-induced cytopathic effects. Methyl cholate exhibits dose-dependent anti-hepatic fibrosis activity in both cellular and zebrafish models, and significantly reduces the expression levels of α-SMA and COL-I. Methyl cholate is suitable for in-depth research in the fields of Clostridioides difficile infection and hepatic fibrosis. | ||||||||||||||||||||
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Ursocholic acid (Standard) | ≥98% | Ursocholic acid (Standard) is the analytical standard of Ursocholic acid. This product is intended for research and analytical applications. Ursocholic acid, a bile acid present in mammalian bile, is converted to deoxycholic acid (UDC) by the mouse intestinal flora. Ursocholic acid acts as a gallstone dissolving agent in the liver through anti-apoptosis, anti-inflammatory, immunomodulatory, bile regulation, and coordinated changes in mitochondrial integrity and cell signaling, Ursocholic acid also has favorable effects on bones in patients with chronic cholestasis. | ||||||||||||||||||||
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Ursodeoxycholic acid-d4 | 99.52% | Ursodeoxycholic acid-2,2,4,4-d4 is the deuterium labeled Ursodeoxycholic acid (HY-13771). Ursodeoxycholic acid is a secondary bile acid issued from the transformation of (cheno)deoxycholic acid by intestinal bacteria, acting as a key regulator of the intestinal barrier integrity and essential for lipid metabolism. Ursodeoxycholic acid acts as signaling molecule, exerting its effects by interacting with bile acid activated receptors, including G-protein coupled bile acid receptor 5 (TGR5, GPCR19) and the farnesoid X receptor (FXR). Ursodeoxycholic acid can be used for the research of a variety of hepatic and gastrointestinal diseases. Ursodeoxycholic acid also reduces ACE2 expression and is beneficial for reducing SARS-CoV-2 infection. | ||||||||||||||||||||
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α-Muricholic acid-d5 | α-Muricholic acid-d5 is the deuterium labeled α-Muricholic acid. α-Muricholic acid is the most abundant primary bile acid in rodents. | |||||||||||||||||||||
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ω-Muricholic Acid-d5 | ω-Muricholic Acid-d5 is the deuterium labeled ω-Muricholic Acid. | |||||||||||||||||||||
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Allocholic acid | Allocholic acid is a typically fetal bile acid found in vertebrates and reappears during liver regeneration and carcinogenesis, besides it is also a conjugate acid of allocholate and an isomer of cholic acid. Allocholic acid is a potent and specific stimulant of the adult olfactory system, it has a role as a marine metabolite, a rat metabolite and a human metabolite. | |||||||||||||||||||||
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Cholic acid 7-sulfate-d4 | Cholic acid 7-sulfate-d4 (7-Sulfocholic acid-d4) is the deuterium labeled Cholic acid 7-sulfate (HY-126855). Cholic acid 7-sulfate is a selective agonist targeting TGR5 (EC50=0.17 μM) and a ligand for MHC class I-related protein (MR1). As a gut-restricted TGR5 agonist, cholic acid 7-sulfate binds to TGR5 on enteroendocrine L cells, induces GLP-1 secretion, and improves glucose tolerance in a TGR5-dependent manner. Cholic acid 7-sulfate also acts as an endogenous ligand for MR1, promoting the survival of mucosal-associated invariant T cells MAIT and the expression of homeostatic gene signatures, affecting MAIT cell development and function. Cholic acid 7-sulfate is mainly used in the research of diabetes and MAIT cell-related immune regulation. | |||||||||||||||||||||
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Ursodeoxycholic acid methyl ester-d5 | Ursodeoxycholic acid-d5 methyl ester is the deuterium labeled Ursodeoxycholic acid methyl ester. | |||||||||||||||||||||
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β-Muricholic acid-d5 | β-Muricholic acid-d5 is the deuterium labeled β-Muricholic acid. | |||||||||||||||||||||
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6-ECDCA-d4 | 6-ECDCA-d4 (6α-ethyl Cheodeoxycholic Acid-d4, Obeticholic Acid-d4) is deuterium labeled 6-ECDCA. | |||||||||||||||||||||
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Homocholic acid | Homocholic acid is a synthetic steroid analogue. Homocholic acid can be labeled with 75Se and is used for SeHCAT detection (a method for diagnosing bile acid malabsorption). | |||||||||||||||||||||
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Chenodeoxycholic Acid-d4 | 99.94% | Chenodeoxycholic Acid-d4 is the deuterium labeled Chenodeoxycholic Acid. Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. | ||||||||||||||||||||
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Chenodeoxycholic acid-d5 | 99.79% | Chenodeoxycholic acid-d5 is the deuterium labeled Chenodeoxycholic Acid. Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. | ||||||||||||||||||||
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Cholic acid sodium | 99.85% | Cholic acid sodium is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid sodium is orally active. | ||||||||||||||||||||
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Cholic acid sodium (Standard) | ≥98% | Cholic acid (sodium) (Standard) is the analytical standard of Cholic acid (sodium). This product is intended for research and analytical applications. Cholic acid sodium is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Cholic acid sodium is orally active. | ||||||||||||||||||||
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Deoxycholic acid-d4 | 99.80% | Deoxycholic acid-d4 is the deuterium labeled Deoxycholic acid. Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity. | ||||||||||||||||||||
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Deoxycholic acid-d5 | 99.9% | Deoxycholic acid-d5 is the deuterium labeled Deoxycholic acid. Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity. | ||||||||||||||||||||
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Deoxycholic acid-d6 | 99.7% | Deoxycholic acid-d6 is the deuterium labeled Deoxycholic acid. Deoxycholic acid is specifically responsible for activating the G protein-coupled bile acid receptor TGR5 that stimulates brown adipose tissue (BAT) thermogenic activity. | ||||||||||||||||||||
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Glycocholic acid-d4 | 99.92% | Glycocholic acid-d4 is the deuterium labeled Glycocholic acid (HY-N1423). Glycocholic acid is a bile acid derivative. Glycocholic acid downregulates MDR1, Bcl-2, MRP1, MRP2 and FXR, upregulates Bax, p53, caspase-9, caspase-3, TGR5 and S1PR2. Glycocholic acid inhibits multidrug resistance and efflux pumps, induces mitochondrial apoptosis, and enhances chemosensitivity. Glycocholic acid modulates related bile acid receptor signaling. Glycocholic acid suppresses growth and conjugation of Enterobacteriaceae and increases their antibiotic susceptibility. Glycocholic acid can be used for the research of colon adenocarcinoma and cholangiocarcinoma (CCA). | ||||||||||||||||||||
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Glycocholic acid-d5 | 99.9% | Glycocholic acid-d5 is the deuterium labeled Glycocholic acid (HY-N1423). Glycocholic acid is a bile acid derivative. Glycocholic acid downregulates MDR1, Bcl-2, MRP1, MRP2 and FXR, upregulates Bax, p53, caspase-9, caspase-3, TGR5 and S1PR2. Glycocholic acid inhibits multidrug resistance and efflux pumps, induces mitochondrial apoptosis, and enhances chemosensitivity. Glycocholic acid modulates related bile acid receptor signaling. Glycocholic acid suppresses growth and conjugation of Enterobacteriaceae and increases their antibiotic susceptibility. Glycocholic acid can be used for the research of colon adenocarcinoma and cholangiocarcinoma (CCA). | ||||||||||||||||||||
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Glycochenodeoxycholic acid-d4 | 99.95% | Glycochenodeoxycholic acid-d4 is the deuterium labeled Glycochenodeoxycholic acid. Glycochenodeoxycholic acid (Chenodeoxycholylglycine) is a bile acid formed in the liver from chenodeoxycholate and glycine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. Glycochenodeoxycholic acid (Chenodeoxycholylglycine) induces hepatocyte apoptosis. | ||||||||||||||||||||
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Norcholic acid | 99.86% | Norcholic acid is a normal minorbile C23 bile acid having four side chain and exsits in human urine and meconium. Norcholic acid can become prominent under certain pathological conditions. Norcholic acid is efficiently absorbed from intestine and quickly excreted into the bile but not into urine. | ||||||||||||||||||||
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Norcholic acid (Standard) | ≥98% | Norcholic acid (Standard) is the analytical standard of Norcholic acid (HY-N9457). This product is intended for research and analytical applications. Norcholic acid is a normal minorbile C23 bile acid having four side chain and exsits in human urine and meconium. Norcholic acid can become prominent under certain pathological conditions. Norcholic acid is efficiently absorbed from intestine and quickly excreted into the bile but not into urine. | ||||||||||||||||||||
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Cholic acid sodium monohydrate | Cholic acid (sodium monohydrate) is a biochemical assay reagent. | |||||||||||||||||||||
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3β-Cholic acid | 99.7% | 3β-Cholic acid is a derivative of cholic acid (HY-N0324), and can be found in human feces. | ||||||||||||||||||||
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12β-Hydroxyisocholic acid | 99.66% | 12β-Hydroxyisocholic acid (Lagocholic acid) is a bile acid isomer that can be used in the study of bile acid metabolism. | ||||||||||||||||||||
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Methyl cholate-d5 | Methyl cholate-d5 is the deuterium labeled Methyl cholate. Methyl cholate is a bile acid analog and a specific inhibitor of TcdB toxin from Clostridioides difficile. Methyl cholate exerts a stronger selective inhibitory effect on TcdB than on TcdA. Methyl cholate induces conformational stabilization by binding to a unique site of TcdB, thereby blocking the binding of the toxin to host receptors and its self-processing process. Methyl cholate effectively protects human fibroblasts from TcdB-induced cytopathic effects. Methyl cholate exhibits dose-dependent anti-hepatic fibrosis activity in both cellular and zebrafish models, and significantly reduces the expression levels of α-SMA and COL-I. Methyl cholate is suitable for in-depth research in the fields of Clostridioides difficile infection and hepatic fibrosis. | |||||||||||||||||||||
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References
- [1]. Li Y, et al. Mechanism of hepatic targeting via oral administration of DSPE-PEG-Cholic acid-modified nanoliposomes. Int J Nanomedicine. 2017 Feb 28;12:1673-1684. [Content Brief]
- [2]. Pan X, et al. Cholic acid Feeding Leads to Increased CYP2D6 Expression in CYP2D6-Humanized Mice. Drug Metab Dispos. 2017 Apr;45(4):346-352. [Content Brief]
