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C1129 Sigma

Cholic acid

from ox or sheep bile, ≥98%

Synonym: 3α,7α,12α-Trihydroxy-5β-cholanic acid, Cholanic acid

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Description

Application

Non-denaturing ionic detergent used for extraction of membrane proteins.

Dietary cholic acid has been used in a study to assess its effect on colonic epithelial cell proliferation. 1 It has also been used in a study to investigate extractions and comparisons of human erythrocyte ghosts. 2

Biochem/physiol Actions

Bile Acid

General description

Cholic acid is a major primary bile acid produced in the liver which facilitates fat absorption and cholesterol excretion. It is a non-denaturing ionic detergent.

Packaging

1 kg in poly bottle

25, 100, 500 g in poly bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1129.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

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Fatty Acid and Sterol Extraction Kits

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Cholic acid
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European Pharmacopoeia (EP) Reference Standard

Deoxycholic acid

≥98% (HPLC)

Lithocholic acid

≥95%

Safety & Documentation

Safety Information

WGK Germany 
2
RTECS 
FZ9350000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Bile Acids

The liver excretes excess cholesterol in the form of bile acids. Bile acids serve two purposes: to remove unwanted cholesterol from the body and to aid in lipid digestion in the intestine. Bile acids...
BioFiles 2007, 2.7, 17.
Keywords: Absorption, Digestions, Transcription

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Acute and Chronic Effect of Dietary Cholic Acid on Colonic Epithelial Cell Proliferation Deschner, E., et al. Digestion 21, 290, (1981)

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2. Detergent extraction of erythrocyte ghosts. Comparison of residues after cholate and Triton x-100 treatments Coleman, R., et al. Biochim. Biophys. Acta 436, 38, (1976)

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Discovery of 6alpha-ethyl-23(S)-methylcholic acid (S-EMCA, INT-777) as a potent and selective agonist for the TGR5 receptor, a novel target for diabesity. Roberto Pellicciari et al J. Med. Chem. 52, 7958-61, (2009)

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Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. Hiroyuki Sato et al J. Med. Chem. 51, 1831-41, (2008)

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Covalently linked trimer of the AcrB multidrug efflux pump provides support for the functional rotating mechanism. Takatsuka Y J. Bacteriol. 191(6), 1729-37, (2009)

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Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Jenny M Pedersen et al J. Med. Chem. 51, 3275-87, (2008)

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Bile-acid-mediated decrease in endoplasmic reticulum stress: a potential contributor to the metabolic benefits of ileal interposition surgery in UCD-T2DM rats. Cummings BP, Bettaieb A, Graham JL, et al. Dis. Model Mech. 6(2), 443-56, (2013)

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Intrahepatic cholestasis of pregnancy levels of sulfated progesterone metabolites inhibit farnesoid X receptor resulting in a cholestatic phenotype. Abu-Hayyeh S, Papacleovoulou G, Lövgren-Sandblom A, et al. Hepatology 57(2), 716-26, (2013)

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Assembly Of Nuclear DNA-encoded Subunits Into Mitochondrial Complex IV, And Their Preferential Integration Into Supercomplex Forms In Patient Mitochondria. Lazarou, M., et al. FASEB J. 276, 6701-13, (2009)

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Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia. Bao-Zhu Yu et al J. Nat. Prod. 72, 24-8, (2009)

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Decreased bile-acid synthesis in livers of hepatocyte-conditional NADPH-cytochrome P450 reductase-null mice results in increased bile acids in serum. Cheng X, Zhang Y, and Klaassen CD J. Pharmacol. Exp. Ther. 351(1), 105-13, (2014)

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MotiveValidator: interactive web-based validation of ligand and residue structure in biomolecular complexes. Vařeková RS, Jaiswal D, Sehnal D, et al. Nucleic Acids Res. 42(Web Server issue), W227-33, (2014)

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Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis. Theofilopoulos S, Wang Y, Kitambi SS, et al. Nat. Chem. Biol. 9(2), 126-33, (2013)

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New photoactive compounds to probe cholic acid and cholesterol inside mixed micelles. Nuin E, Gómez-Mendoza M, Andreu I, et al. Org. Lett. 15(2), 298-301, (2013)

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Alteration of bile acid metabolism in pseudo germ-free rats [corrected]. Bhowmik SK, An JH, Lee SH, et al. Arch. Pharm. Res. 35(11), 1969-77, (2012)

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Hepatic overexpression of Abcb11 in mice promotes the conservation of bile acids within the enterohepatic circulation. Henkel AS, Gooijert KE, Havinga R, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 304(2), G221-6, (2013)

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Effects of bile duct ligation and cholic acid treatment on fatty liver in two rat models of non-alcoholic fatty liver disease. Gabbi C, Bertolotti M, Anzivino C, et al. Dig. Liver Dis. 44(12), 1018-26, (2012)

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Synthesis and antimicrobial activity of cholic acid hydrazone analogues. Rasras, A., J., M.; et al. Eur. J. Med. Chem. 45, 2307, (2010)

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Nongenomic actions of bile acids. Synthesis and preliminary characterization of 23- and 6,23-alkyl-substituted bile acid derivatives as selective modulators for the G-protein coupled receptor TGR5. Pellicciari, R., et al J. Med. Chem. 50, 4265-4268, (2007)

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Examination Of Campylobacter Jejuni Putative Adhesins Leads To The Identification Of A New Protein, Designated FlpA, Required For Chicken Colonization. Flanagan, R.C., et al. Infect. Immun. 77, 2399-407, (2009)

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Fluorescence (fluidity/hydration) and calorimetric studies of interactions of bile acid-drug conjugates with model membranes. Sreekanth V and Bajaj A J. Phys. Chem. B 117(7), 2123-33, (2013)

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Deciphering the role of charge, hydration, and hydrophobicity for cytotoxic activities and membrane interactions of bile acid based facial amphiphiles. Singh M, Singh A, Kundu S, et al. Biochim. Biophys. Acta 1828(8), 1926-37, (2013)

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Effects of amphiphilic star-shaped poly(ethylene glycol) polymers with a cholic acid core on human red blood cell aggregation. Janvier F, Zhu JX, Armstrong J, et al. J. Mech. Behav. Biomed. Mater. 18, 100-7, (2013)

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Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli. Christopher A Elkins et al Antimicrob. Agents Chemother. 51, 923-9, (2007)

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Bile acid toxicity structure-activity relationships: correlations between cell viability and lipophilicity in a panel of new and known bile acids using an oesophageal cell line (HET-1A). Ruchika Sharma et al Bioorg. Med. Chem. 18, 6886-95, (2010)

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Amphiphilic N-(2,3-dihydroxypropyl)-chitosan-cholic acid micelles for paclitaxel delivery. Pan Z, Gao Y, Heng L, et al. Carbohydr. Polym. 94(1), 394-9, (2013)

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Cholic acid for hepatic steatosis in patients with lipodystrophy: a randomized, controlled trial. Ahmad Z, Subramanyam L, Szczepaniak L, et al. Eur. J. Endocrinol. 168(5), 771-8, (2013)

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X-linked Cholestasis In Mouse Due To Mutations Of The P4-ATPase ATP11C. Siggs, O.M., et al. Proc. Natl. Acad. Sci. U. S. A. 108, 7890-5, (2011)

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Two new cholic acid derivatives from the marine ascidian-associated bacterium Hasllibacter halocynthiae. Kim SH, Shin YK, Sohn YC, et al. Molecules 17(10), 12357-64, (2012)

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Involvement of SIK3 in glucose and lipid homeostasis in mice. Uebi T, Itoh Y, Hatano O, et al. PLoS ONE 7(5), e37803, (2012)

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Amphiphilic cholic-acid-modified dextran sulfate and its application for the controlled delivery of superoxide dismutase. Xiong Y, Qi J, and Yao P Macromol. Biosci. 12(4), 515-24, (2012)

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The generalized identification of truly interfacial molecules (ITIM) algorithm for nonplanar interfaces. Sega M, Kantorovich SS, Jedlovszky P, et al. J. Chem. Phys. 138(4), 044110, (2013)

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Preparation, preliminary screening of new types of steroid conjugates and their activities on steroid receptors. Jurášek M, Džubák P, Sedlák D, et al. Steroids 78(3), 356-61, (2013)

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StAR-related lipid transfer domain protein 5 binds primary bile acids. Létourneau D, Lorin A, Lefebvre A, et al. J. Lipid Res. 53(12), 2677-89, (2012)

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Synthesis and SAR of 2-aryl-3-aminomethylquinolines as agonists of the bile acid receptor TGR5. Mark R Herbert et al Bioorg. Med. Chem. Lett. 20, 5718-21, (2010)

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Inhibition Of Human Peptide Deformylase Disrupts Mitochondrial Function. Escobar-Alvarez, S., et al. Mol. Cell. Biol. 30, 5099-109, (2010)

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Delineation of biochemical, molecular, and physiological changes accompanying bile acid pool size restoration in Cyp7a1(-/-) mice fed low levels of cholic acid. Jones RD, Repa JJ, Russell DW, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 303(2), G263-74, (2012)

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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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Aggregation behavior of ibuprofen, cholic acid and dodecylphosphocholine micelles. Prakash P, Sayyed-Ahmad A, Zhou Y, et al. Biochim. Biophys. Acta 1818(12), 3040-7, (2012)

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Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: impending synergistic agents. Sudhir N Bavikar et al Bioorg. Med. Chem. Lett. 18, 5512-7, (2008)

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Synthesis of bile acid derivatives and in vitro cytotoxic activity with pro-apoptotic process on multiple myeloma (KMS-11), glioblastoma multiforme (GBM), and colonic carcinoma (HCT-116) human cell lines. Dominique Brossard et al Eur. J. Med. Chem. 45, 2912-8, (2010)

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Ice-like encapsulated water by two cholic acid moieties. Soto VH, Alvarez M, Meijide F, et al. Steroids 77(12), 1228-32, (2012)

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Bile acids repress hypoxia-inducible factor 1 signaling and modulate the airway immune response. Legendre C, Reen FJ, Woods DF, et al. Infect. Immun. 82(9), 3531-41, (2014)

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Amino functionalized novel cholic acid derivatives induce HIV-1 replication and syncytia formation in T cells. Deepak B Salunke et al J. Med. Chem. 49, 2652-5, (2006)

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Single nucleotide polymorphism analysis of the major tripartite multidrug efflux pump of Escherichia coli: functional conservation in disparate animal reservoirs despite exposure to antimicrobial chemotherapy. Christopher A Elkins et al Antimicrob. Agents Chemother. 54, 1007-15, (2010)

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Intestine-specific deletion of SIRT1 in mice impairs DCoH2-HNF-1α-FXR signaling and alters systemic bile acid homeostasis. Kazgan N, Metukuri MR, Purushotham A, et al. Gastroenterology 146(4), 1006-16, (2014)

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The effect of physiological concentrations of bile acids on in vitro growth of Mycobacterium tuberculosis. Epstein D, Mistry K, Whitelaw A, et al. S. Afr. Med. J. 102(6), 522-4, (2012)

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Effects of restructured pork containing Himanthalia elongata on adipose tissue lipogenic and lipolytic enzyme expression of normo- and hypercholesterolemic rats. González-Torres L, Churruca I, Schultz Moreira AR, et al. J. Nutrigenet. Nutrigenomics 5(3), 158-67, (2012)

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Variations in target gene expression and pathway profiles in the mouse hippocampus following treatment with different effective compounds for ischemia-reperfusion injury. Chen Y, Zhou C, Yu Y, et al. Naunyn Schmiedebergs Arch. Pharmacol. 385(8), 797-806, (2012)

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Dansyl-labeled cholic acid as a tool to build speciation diagrams for the aggregation of bile acids. Gomez-Mendoza M, Marin ML, and Miranda MA J. Phys. Chem. B 116(51), 14776-80, (2012)

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Progressive familial intrahepatic cholestasis and inborn errors of bile acid synthesis. Jankowska I and Socha P Clin. Res. Hepatol. Gastroenterol. 36(3), 271-4, (2012)

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Protective effect of grape by-product-fortified breads against cholesterol/cholic acid diet-induced hypercholesterolaemia in rats. Mildner-Szkudlarz S and Bajerska J J. Sci. Food Agric. 93(13), 3271-8, (2013)

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Towards squalamine mimics: synthesis and antibacterial activities of head-to-tail dimeric sterol-polyamine conjugates. Chen WH, Wennersten C, Moellering RC, et al. Chem. Biodivers. 10(3), 385-93, (2013)

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Phosphatidylcholine attenuates aggregation of nonsteroidal anti-inflammatory drugs with bile acid. Prakash P and Gorfe AA Biochemistry 52(42), 7461-9, (2013)

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Hydroxylation of lithocholic acid by selected actinobacteria and filamentous fungi. Kollerov VV, Monti D, Deshcherevskaya NO, et al. Steroids 78(3), 370-8, (2013)

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A possible role of chenodeoxycholic acid and glycine-conjugated bile acids in fibrotic steatohepatitis in a dietary rat model. Jia X, Suzuki Y, Naito H, et al. Dig. Dis. Sci. 59(7), 1490-501, (2014)

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Regulation of host weight gain and lipid metabolism by bacterial bile acid modification in the gut. Joyce SA, MacSharry J, Casey PG, et al. Proc. Natl. Acad. Sci. U. S. A. 111(20), 7421-6, (2014)

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Ameliorative effects of a combination of baicalin, jasminoidin and cholic acid on ibotenic acid-induced dementia model in rats. Zhang J, Li P, Wang Y, et al. PLoS ONE 8(2), e56658, (2013)

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Merck 14,2203

Beil. 10,IV,2072

FT-IR 2 (3), 4240:B / FT-IR 1 (2), 1057:C / FT-NMR 1 (3), 594:B / IR-Spectra (3), 1499:G / IR-Spectra (2), 1282:C / NMR-Reference 2 (2), 929:A / RegBook 1 (2), 2867:M / Sax 6, 788 / Sigma FT-IR 1 (1), 1221:D / Structure Index 1, 459:A:6

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