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Chemical Structure
Chemical Structure
Chemical Structure

Chenodeoxycholic acid [474-25-9]

Research Use Only
AG-CN2-0410
AdipoGen Life Sciences
CAS Number474-25-9
Product group Chemicals
Estimated Purity>95%
Molecular Weight392.6
Price on request
Packing Size
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Chenodeoxycholic acid [474-25-9]
  • Delivery Days Customer
    10
  • CAS Number
    474-25-9
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Hazard Information
    Warning
  • Molecular Formula
    C24H40O4
  • Molecular Weight
    392.6
  • Scientific Description
    Chemical. CAS: 474-25-9. Formula: C24H40O4. MW: 392.6. Synthetic. Originally isolated from bile. Cytotoxic hydrophobic primary bile acid. Activator of farnesoid X receptor (FXR), a nuclear receptor that is hepatoprotective and regulates bile acid synthesis (cholesterol 7alpha-hydroxylase (CYP7A1) suppression), conjugation and transport, as well as genes involved in lipid and glucose metabolism and. Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, insulin resistance, hyperlipidemia and atherosclerosis. Inhibitor of 5beta-reductase (AKR1D1). Potent selective inhibitor of DD2 (AKR1C2). Potent inhibitor of 11beta-HSD1 dehydrogenase. Changes tumor cell viability via IL-6 pathway. Anticancer compound. Apoptosis inducer. Immunosuppressive and anti-inflammatory compound. Modulates oxidative stress. Differentiation regulator of mouse embryonic stem cells. Used for dissolution of cholesterol gallstones. - Cytotoxic hydrophobic primary bile acid [1]. Activator of farnesoid X receptor (FXR), a nuclear receptor that is hepatoprotective and regulates bile acid synthesis (cholesterol 7alpha-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 5beta-reductase (AKR1D1) [10, 15]. Potent selective inhibitor of DD2 (AKR1C2) [3]. Potent inhibitor of 11beta-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.
  • 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
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

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)