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Chemical Structure
Chemical Structure
Chemical Structure

Ursodeoxycholic acid [128-13-2]

Research Use Only
AG-CN2-0411
AdipoGen Life Sciences
CAS Number128-13-2
Product group Chemicals
Estimated Purity>95%
Molecular Weight392.6
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Ursodeoxycholic acid
  • Delivery Days Customer
    10
  • CAS Number
    128-13-2
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Hazard Information
    Warning
  • Molecular Formula
    C24H40O4
  • Molecular Weight
    392.6
  • Scientific Description
    Chemical. CAS: 128-13-2. Formula: C24H40O4. MW: 392.6. Synthetic. Endogenous hydrophilic bile acid. Antioxidant. Cytoprotective against oxidative stress and cell death. Hepatoprotective at cellular and molecular level, including stabilization of membranes. Protects hepatocytes against bile acid-induced apoptosis. Antiapoptotic and antinecrotic. Targets the mitochondrial function and integrity, reduction of endoplasmatic stress and interactions with survival signals in cAMP, Akt, NF-kappaB, MAPK and PI3K signaling pathways. Modulator and finetuner of the p53-Mdm-2 complex. Chemopreventive against colorectal cancer by countering the tumor-promoting effects of secondary bile acids. Shows also effects on epidermal growth factor receptor (EGFR) signaling and COX-2 expression. Immunomodulator and anti-inflammatory compound. Modifies TLR4 and TLR9 signaling pathways and downregulates the production of proinflammatory tumor necrosis factor-alpha (TNF-alpha). Pregnane X receptor agonist. Neuroprotective. Inhibits neuronal apoptosis. Glucocorticoid Receptor (GR) agonist. Anticholestatic agent. Used to reduce cholesterol absorption and for cholesterol gallstone dissolution. Used to treat primary biliary cirrhosis (PBC). Interferes with the progression of non-alcoholic fatty liver disease (NAFLD)/NASH. Reduces CXCR3 expression. TIMP-1 inducer. ADAM17 inhibitor. - Endogenous hydrophilic bile acid. Antioxidant. Cytoprotective against oxidative stress and cell death. Hepatoprotective at cellular and molecular level, including stabilization of membranes. Protects hepatocytes against bile acid-induced apoptosis. Antiapoptotic and antinecrotic. Targets the mitochondrial function and integrity, reduction of endoplasmatic stress and interactions with survival signals in cAMP, Akt, NF-kappaB, MAPK and PI3K signaling pathways. Modulator and finetuner of the p53-Mdm-2 complex. Chemopreventive against colorectal cancer by countering the tumor-promoting effects of secondary bile acids. Shows also effects on epidermal growth factor receptor (EGFR) signaling and COX-2 expression. Immunomodulator and anti-inflammatory compound. Modifies TLR4 and TLR9 signaling pathways and downregulates the production of proinflammatory tumor necrosis factor-alpha (TNF-alpha). Pregnane X receptor agonist. Neuroprotective. Inhibits neuronal apoptosis. Glucocorticoid Receptor (GR) agonist. Anticholestatic agent. Used to reduce cholesterol absorption and for cholesterol gallstone dissolution. Used to treat primary biliary cirrhosis (PBC). Interferes with the progression of non-alcoholic fatty liver disease (NAFLD)/NASH. Reduces CXCR3 expression [11]. TIMP-1 inducer [12]. ADAM17 inhibitor [12].
  • 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
  • UNSPSC
    12352200

References

  • Antioxidant properties of ursodeoxycholic acid: D. Lapenna, et al.; Biochem. Pharmacol. 64, 1661 (2002) (Review)
  • Ursodeoxycholic acid in cholestatic liver disease: mechanisms of action and therapeutic use revisited: G. Paumgartner, et al.; Hepatology 36, 525 (2002) (Review)
  • Nonalcoholic fatty liver disease: an overview of current insights in pathogenesis, diagnosis and treatmen. T.C. Schreuder, et al.; World J. Gastroenterol. 14, 2474 (2008) (Review)
  • p53 and the regulation of hepatocyte apoptosis: implications for disease pathogenesis: J.D. Amaral, et al.; Trends Mol. Med. 15, 531 (2009) (Review)
  • Bile acids: regulation of apoptosis by ursodeoxycholic acid: J.D. Amaral, et al.; J. Lipid. Res. 50, 1721 (2009) (Review)
  • Bile acids as regulators of hepatic lipid and glucose metabolism: M. Trauner, et al.; Dig. Dis. 28, 220 (2010) (Review)
  • Targeting the p53 pathway of apoptosis: J.D. Amaral, et al.; Curr. Pharm. Des. 16, 2493 (2010) (Review)
  • Ursodeoxycholic acid and chemoprevention of colorectal cancer: L. Serfaty, et al.; Gastroenterol. Clin. Biol. 34, 516 (2010) (Review)
  • Ursodeoxycholic acid and bile-acid mimetics as therapeutic agents for cholestatic liver diseases: an overview of their mechanisms of action: R. Poupon; Clin. Res. Hepatol. Gastroenterol. 36, S3 (2012) (Review)
  • Ursodeoxycholic acid in cholestasis: linking action mechanisms to therapeutic applications: M.G. Roma, et al.; Clin. Sci. (Lond). 121, 523 (2011) (Review)