Cholic acid

Details:

Chemical Properties of Cholic acid

Cas No.	81-25-4
PubChem ID	221493	Appearance	White powder
Formula	C24H40O5	M.Wt	408.6
Type of Compound	Steroids	Storage	Desiccate at -20°C
Solubility	DMSO : ≥ 50 mg/mL (122.38 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown.
Chemical Name	(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
SMILES	CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
Standard InChIKey	BHQCQFFYRZLCQQ-OELDTZBJSA-N
Standard InChI	InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cholic acid

The bile of Pig

Biological Activity of Cholic acid

Description	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. It prevents hepatic TG accumulation, VLDL secretion, and elevated serum TG in mouse models of hypertriglyceridemia;at the molecular level, CA decreases hepatic expression of SREBP-1c and its lipogenic target genes.
Targets	cAMP | Sodium Channel | SREBP-1c
In vitro	Design of β-CD-surfactant complex-coated liquid crystal droplets for the detection of cholic acid via competitive host-guest recognition.[Pubmed: 25892566] Chem Commun (Camb). 2015 Apr 20. β-CD-C14TAB complex-coated 5CB droplets are designed by the adsorption of β-CD-C14TAB complexes at the 5CB/aqueous interface. We show that the 5CB droplets can be used as an optical probe for the selective detection of Cholic acid in aqueous solution containing uric acid and urea via competitive host-guest recognition.
In vivo	Cholic acid induces a Cftr dependent biliary secretion and liver growth response in mice.[Pubmed: 25680200] PLoS One. 2015 Feb 13;10(2):e0117599. The cause of Cystic fibrosis liver disease (CFLD), is unknown. It is well recognized that hepatic exposure to hydrophobic bile salts is associated with the development of liver disease. For this reason, we hypothesize that, CFTR dependent variations, in the hepatic handling of hydrophobic bile salts, are related to the development CFLD. METHODS AND RESULTS: To test our hypothesis we studied, in Cftr-/- and control mice, bile production, bile composition and liver pathology, in normal feeding condition and during cholate exposure, either acute (intravenous) or Cholic acid (three weeks via the diet). In Cftr-/- and control mice the basal bile production was comparable. Intravenous taurocholate increased bile production to the same extent in Cftr-/- and control mice. However, Cholic acid cholate exposure increased the bile flow significantly less in Cftr-/- mice than in controls, together with significantly higher biliary bile salt concentration in Cftr-/- mice. Prolonged cholate exposure, however, did not induce CFLD like pathology in Cftr-/- mice. Cholic acid cholate exposure did induce a significant increase in liver mass in controls that was absent in Cftr-/- mice. Cholic acid cholate administration induces a cystic fibrosis-specific hepatobiliary phenotype, including changes in bile composition. These changes could not be associated with CFLD like pathological changes in CF mouse livers. However, Cholic acid cholate administration induces liver growth in controls that is absent in Cftr-/- mice. CONCLUSIONS: Our findings point to an impaired adaptive homeotrophic liver response to prolonged hydrophobic bile salt exposure in CF conditions.

Protocol of Cholic acid

Cell Research

Bile acids lower triglyceride levels via a pathway involving FXR, SHP, and SREBP-1c.[Pubmed: 15146238 ] J Clin Invest. 2004 May;113(10):1408-18. METHODS AND RESULTS: We explored the effects of bile acids on triglyceride (TG) homeostasis using a combination of molecular, cellular, and animal models. Cholic acid (CA) prevents hepatic TG accumulation, VLDL secretion, and elevated serum TG in mouse models of hypertriglyceridemia. At the molecular level, CA decreases hepatic expression of SREBP-1c and its lipogenic target genes. Through the use of mouse mutants for the short heterodimer partner (SHP) and liver X receptor (LXR) alpha and beta, we demonstrate the critical dependence of the reduction of SREBP-1c expression by either natural or synthetic farnesoid X receptor (FXR) agonists on both SHP and LXR alpha and LXR beta. CONCLUSIONS: These results suggest that strategies aimed at increasing FXR activity and the repressive effects of SHP should be explored to correct hypertriglyceridemia.

Animal Research

Diet supplementation with cholic acid promotes intestinal epithelial proliferation in rats exposed to γ-radiation.[Pubmed: 25455456] Toxicol Lett. 2014 Oct 17;232(1):246-252. Consumption of a high-fat diet increases some secondary bile acids (BAs) such as deoxyCholic acid (DCA) in feces. DCA is derived from Cholic acid (CA), a primary BA. METHODS AND RESULTS: We evaluated intestinal epithelial proliferation and BA metabolism in response to oral administration of Cholic acid (CA) in rats to determine the influence of a CA diet on the responses of gut epithelia to γ-rays. WKAH/HkmSlc rats were divided into two dietary groups: control diet or CA-supplemented (2g/kg diet) diet. Some of the rats from each group were irradiated with γ-rays, and epithelial cell proliferation in the colon was analyzed histochemically. Unirradiated CA-fed rats had high levels of DCA and CA in the sera, as well as the presence of tauroCholic acid in their feces. Significant increases were observed in both epithelial proliferation and the number of epithelial cells in the colon of the CA-fed rats, and this effect was observed at 8 weeks after γ-ray exposure. Furthermore, extracts from both cecal contents and sera of the unirradiated CA-fed rats promoted proliferation of IEC-6 cells. CONCLUSIONS: These results indicate that BAs in enterohepatic circulation promote proliferation and survival of the intestinal epithelium after receiving DNA damage.

Preparing Stock Solutions of Cholic acid

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.4474 mL	12.2369 mL	24.4738 mL	48.9476 mL	61.1845 mL
5 mM	0.4895 mL	2.4474 mL	4.8948 mL	9.7895 mL	12.2369 mL
10 mM	0.2447 mL	1.2237 mL	2.4474 mL	4.8948 mL	6.1185 mL
50 mM	0.0489 mL	0.2447 mL	0.4895 mL	0.979 mL	1.2237 mL
100 mM	0.0245 mL	0.1224 mL	0.2447 mL	0.4895 mL	0.6118 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

 

References on Cholic acid

Diet supplementation with cholic acid promotes intestinal epithelial proliferation in rats exposed to gamma-radiation.[Pubmed:25455456]

Toxicol Lett. 2015 Jan 5;232(1):246-52.

Consumption of a high-fat diet increases some secondary bile acids (BAs) such as deoxyCholic acid (DCA) in feces. DCA is derived from Cholic acid (CA), a primary BA. We evaluated intestinal epithelial proliferation and BA metabolism in response to oral administration of Cholic acid (CA) in rats to determine the influence of a CA diet on the responses of gut epithelia to gamma-rays. WKAH/HkmSlc rats were divided into two dietary groups: control diet or CA-supplemented (2g/kg diet) diet. Some of the rats from each group were irradiated with gamma-rays, and epithelial cell proliferation in the colon was analyzed histochemically. Unirradiated CA-fed rats had high levels of DCA and CA in the sera, as well as the presence of tauroCholic acid in their feces. Significant increases were observed in both epithelial proliferation and the number of epithelial cells in the colon of the CA-fed rats, and this effect was observed at 8 weeks after gamma-ray exposure. Furthermore, extracts from both cecal contents and sera of the unirradiated CA-fed rats promoted proliferation of IEC-6 cells. These results indicate that BAs in enterohepatic circulation promote proliferation and survival of the intestinal epithelium after receiving DNA damage.

Cholic acid induces a Cftr dependent biliary secretion and liver growth response in mice.[Pubmed:25680200]

PLoS One. 2015 Feb 13;10(2):e0117599.

The cause of Cystic fibrosis liver disease (CFLD), is unknown. It is well recognized that hepatic exposure to hydrophobic bile salts is associated with the development of liver disease. For this reason, we hypothesize that, CFTR dependent variations, in the hepatic handling of hydrophobic bile salts, are related to the development CFLD. To test our hypothesis we studied, in Cftr-/- and control mice, bile production, bile composition and liver pathology, in normal feeding condition and during cholate exposure, either acute (intravenous) or chronic (three weeks via the diet). In Cftr-/- and control mice the basal bile production was comparable. Intravenous taurocholate increased bile production to the same extent in Cftr-/- and control mice. However, chronic cholate exposure increased the bile flow significantly less in Cftr-/- mice than in controls, together with significantly higher biliary bile salt concentration in Cftr-/- mice. Prolonged cholate exposure, however, did not induce CFLD like pathology in Cftr-/- mice. Chronic cholate exposure did induce a significant increase in liver mass in controls that was absent in Cftr-/- mice. Chronic cholate administration induces a cystic fibrosis-specific hepatobiliary phenotype, including changes in bile composition. These changes could not be associated with CFLD like pathological changes in CF mouse livers. However, chronic cholate administration induces liver growth in controls that is absent in Cftr-/- mice. Our findings point to an impaired adaptive homeotrophic liver response to prolonged hydrophobic bile salt exposure in CF conditions.

Bile acids lower triglyceride levels via a pathway involving FXR, SHP, and SREBP-1c.[Pubmed:15146238]

J Clin Invest. 2004 May;113(10):1408-18.

We explored the effects of bile acids on triglyceride (TG) homeostasis using a combination of molecular, cellular, and animal models. Cholic acid (CA) prevents hepatic TG accumulation, VLDL secretion, and elevated serum TG in mouse models of hypertriglyceridemia. At the molecular level, CA decreases hepatic expression of SREBP-1c and its lipogenic target genes. Through the use of mouse mutants for the short heterodimer partner (SHP) and liver X receptor (LXR) alpha and beta, we demonstrate the critical dependence of the reduction of SREBP-1c expression by either natural or synthetic farnesoid X receptor (FXR) agonists on both SHP and LXR alpha and LXR beta. These results suggest that strategies aimed at increasing FXR activity and the repressive effects of SHP should be explored to correct hypertriglyceridemia.

Design of beta-CD-surfactant complex-coated liquid crystal droplets for the detection of cholic acid via competitive host-guest recognition.[Pubmed:25892566]

Chem Commun (Camb). 2015 May 28;51(43):8912-5.

beta-CD-C14TAB complex-coated 5CB droplets are designed by the adsorption of beta-CD-C14TAB complexes at the 5CB/aqueous interface. We show that the 5CB droplets can be used as an optical probe for the selective detection of Cholic acid in aqueous solution containing uric acid and urea via competitive host-guest recognition.

Hydrophilic modification of PVDF microfiltration membranes by adsorption of facial amphiphile cholic acid.[Pubmed:25454658]

Colloids Surf B Biointerfaces. 2014 Nov 1;123:809-13.

Amphiphilic molecules have been widely used in surface modification of polymeric materials. Bile acids are natural biological compounds and possess special facial amphiphilic structure with a unusual distribution of hydrophobic and hydrophilic regions. Based on the facial amphiphilicity, Cholic acid (CA), one of the bile acids, was utilized for the hydrophilic modification of poly(vinylidene fluoride) (PVDF) microfiltration membranes via the hydrophobic interactions between the hydrophobic face of CA and the membrane surfaces. Ethanol, methanol, and water were respectively used as solvent during CA adsorption procedure. Their polarity affects the CA adsorption amount, as similar to CA concentration and adsorption time. There are no changes on the membrane surface morphology after CA adsorption. The hydrophilicity of PVDF membranes is greatly enhanced and the water drops permeates into the CA modified membranes quickly after modification. All these factors benefit to the permeation flux of membrane for water. When CA concentration is higher than 0.088 M, the water permeation flux is doubled as compared with the nascent PVDF membrane and shows a good stability during filtration procedure. These results reveal the promising potential of facial amphiphilic bile acids for the surface modification of polymeric materials.

Description

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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