Chenodeoxycholic acid

Specifications / Handling

More Information
Product Details
Synonyms	CDCA; Ulmenide; Kebilis; Hekbilin; Fluibil; Chenodiol; Anthropodeoxycholic acid
Product Type	Chemical
Properties
Formula	C₂₄H₄₀O₄
MW	392.6
Merck Index	14: 2054
CAS	474-25-9
RTECS	FZ1980000
Source/Host Chemicals	Synthetic. Originally isolated from bile.
Purity Chemicals	≥95%
Appearance	White to off-white crystalline powder.
Solubility	Soluble in DMSO, ethanol or dimethylformamide. Sparingly soluble in water.
Identity	Determined by IR
InChi Key	RUDATBOHQWOJDD-BSWAIDMHSA-N
Smiles	[H][C@@]1(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])CC[C@]12C)[C@H](C)CCC(O)=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light. Protect from moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Cytotoxic hydrophobic primary bile acid [1].
Activator of farnesoid X receptor (FXR), a nuclear receptor that is hepatoprotective and regulates bile acid synthesis (cholesterol 7α-hydroxylase (CYP7A1) suppression), conjugation and transport, as well as genes involved in lipid and glucose metabolism and [4-6, 14].
Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, insulin resistance, hyperlipidemia and atherosclerosis [1, 8, 9, 12].
Inhibitor of 5β-reductase (AKR1D1) [10, 15].
Potent selective inhibitor of DD2 (AKR1C2) [3].
Potent inhibitor of 11β-HSD1 dehydrogenase [7].
Changes tumor cell viability via IL-6 pathway [11].
Anticancer compound. Apoptosis inducer [13].
Immunosuppressive and anti-inflammatory compound. Modulates oxidative stress [2, 16].
Differentiation regulator of mouse embryonic stem cells [17].
Used for dissolution of cholesterol gallstones.

Product References

Bile acids as drugs: principles, mechanisms of action and formulations: A.F. Hofmann; Ital. J. Gastroenterol. 27, 106 (1995) (Review)
S-adenosil-L-methionine is able to reverse the immunosuppressive effects of chenodeoxycholic acid in vitro: G. Filaci, et al.; Int. J. Immunopharmacol. 19, 157 (1997)
Identification of amino acid residues responsible for differences in substrate specificity and inhibitor sensitivity between two human liver dihydrodiol dehydrogenase isoenzymes by site-directed mutagenesis: K. Matsuura, et al.; Biochem. J. 323, 61 (1997)
Identification of a nuclear receptor for bile acids: M. Makishima, et al.; Science 284, 1362 (1999)
Bile acids: natural ligands for an orphan nuclear receptor: D.J. Parks, et al.; Science 284, 1365 (1999) (Review)
A natural product that lowers cholesterol as an anatagonist ligand for FXR: N.L. Urizar, et al.; Science 296, 1703 (2002)
Effect of chenodeoxycholic acid on 11beta-hydroxysteroid dehydrogenase in various target tissues: D.J. Morris, et al.; Metabolism 53, 811 (2004)
The Farnesoid X Receptor - A Molecular Link Between Bile Acid and Lipid and Glucose Metabolism: T. Claudel, et al.; Hepatology 48, 1632 (2008) (Review)
Farnesoid X receptor antagonizes nuclear factor kappaB in hepatic inflammatory response: Y.D. Wang, et al.; Hepatology 48, 1632 (2008) (Review)
Bile acids modulate glucocorticoid metabolism and the hypothalamic-pituitary-adrenal axis in obstructive jaundice: A.D. McNeilly, et al.; J. Hepatol. 52, 705 (2010)
Effects of bile acids on expression of interleukin-6 and cell viability in QBC939 cell line: J. Wang, et al.; Zhonghua Wai Ke Za Zhi. 48, 919 (2010)
Fasting plasma chenodeoxycholic acid and cholic acid concentrations are inversely correlated with insulin sensitivity in adults: B. Cariou, et al.; Nutrition & Metabolism 8, 48 (2011)
Deoxycholic and chenodeoxycholic bile acids induce apoptosis via oxidative stress in human colon adenocarcinoma cells: J.I. Barrasa, et al.; Apoptosis 16, 1054 (2011)
Farnesoid X receptor activation by chenodeoxycholic acid induces detoxifying enzymes through AMP-activated protein kinase and extracellular signal-regulated kinase 1/2-mediated phosphorylation of CCAAT/enhancer binding protein β: K. Noh, et al.; Drug Metab. Dispos. 39, 1451 (2011)
Substrate specificity and inhibitor analyses of human steroid 5β-reductase (AKR1D1): M. Chen, et al.; Steroids 76, 484 (2011)
Effect of chenodeoxycholic acid on fibrosis, inflammation and oxidative stress in kidney in high-fructose-fed Wistar rats: Z. Hu, et al.; Kidney Blood Press Res. 36, 85 (2012)
Direct effect of chenodeoxycholic acid on differentiation of mouse embryonic stem cells cultured under feeder-free culture conditions: S.J. Park, et al.; Biomed. Res. Int. 2013, 375076 (2013)

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