Available from stock

Ursodeoxycholic acid

SKU: U0019

Category: Lipids, Fatty Acids

Synonyms: UDCA , USAN , BRN 3219888 , NSC 657950 , NSC 683769 , 3α,7β-Dihydroxy-5β-cholan-24-oic acid , 5β-Cholan-24-oic acid-3α,7β-diol , 7β-Hydroxylithocholic acid , UDCS; 128-13-2
CAS-Number: C₂₄H₄₀O₄
Molecular Formula: 392.57
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥99% (T)
Appearance: White to off-white powder
Identity: 1H-NMR

Properties

Solvents: ethanol, DMSO
Melting Point: 203-204 °C (lit.)

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: +4°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Transportation: Not dangerous goods

Description: Endogenous hydrophilic bile acid. Antioxidant. Cytoprotective against oxidative stress and cell death. Hepatoprotective at cellular and molecular level, including stabilization of membranes. Antiapoptotic and antinecrotic. Targets the mitochondrial function and integrity, reduction of endoplasmatic stress and interactions with survival signals in cAMP, Akt, NF-kB, MAPK and PI3K signaling pathways. 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-α (TNF-α). Pregnane X receptor agonist. Neuroprotective. Anticholestatic agent. Used to reduce cholesterol absorption and for cholesterol gallstone dissolution.
Smiles: [H][C@]1([C@@H](CCC(O)=O)C)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@@]21C
InChi Key: RUDATBOHQWOJDD-UZVSRGJWSA-N
References: (1) D. Lapenna, et al., Biochem. Pharmacol. 64, 1661 (2002) (Review) , (2) G. Paumgartner, et al., Hepatology 36, 525 (2002) (Review) , (3) T.C. Schreuder, et al., World J. Gastroenterol. 14, 2474 (2008) (Review) , (4) J.D. Amaral, et al., Trends Mol. Med. 15, 531 (2009) (Review) , (5) J.D. Amaral, et al., J. Lipid. Res. 50, 1721 (2009) (Review) , (6) M. Trauner, et al., Dig. Dis. 28, 220 (2010) (Review) , (7) J.D. Amaral, et al., Curr. Pharm. Des. 16, 2493 (2010) (Review) , (8) L. Serfaty, et al., Gastroenterol. Clin. Biol. 34, 516 (2010) (Review) , (9) M.G. Roma, et al., Clin. Sci. (Lond). 121, 523 (2011) (Review)
InChi: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1

Endogenous hydrophilic bile acid. Antioxidant. Cytoprotective against oxidative stress and cell death. Hepatoprotective at cellular and molecular level, including stabilization of membranes. Antiapoptotic and antinecrotic. Targets the mitochondrial function and integrity, reduction of endoplasmatic stress and interactions with survival signals in cAMP, Akt, NF-kB, MAPK and PI3K signaling pathways. 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-α (TNF-α). Pregnane X receptor agonist. Neuroprotective. Anticholestatic agent. Used to reduce cholesterol absorption and for cholesterol gallstone dissolution.

SKU: U0019 Category: Lipids, Fatty Acids

Additional information

Additional information

Synonyms	UDCA, USAN, BRN 3219888, NSC 657950, NSC 683769, 3α,7β-Dihydroxy-5β-cholan-24-oic acid, 5β-Cholan-24-oic acid-3α,7β-diol, 7β-Hydroxylithocholic acid, UDCS
Purity	≥99% (T)
Appearance	White to off-white powder
CAS-Number	128-13-2
Molecular Formula	C24H40O4
Molecular Weight	392.57
Identity	1H-NMR
Solvents	ethanol, DMSO
Melting Point	203-204 °C (lit.)
Smiles	[H][C@]1([C@@H](CCC(O)=O)C)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@@]21C
InChi Key	RUDATBOHQWOJDD-UZVSRGJWSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	+4°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Transportation	Not dangerous goods
References	(1) D. Lapenna, et al., Biochem. Pharmacol. 64, 1661 (2002) (Review), (2) G. Paumgartner, et al., Hepatology 36, 525 (2002) (Review), (3) T.C. Schreuder, et al., World J. Gastroenterol. 14, 2474 (2008) (Review), (4) J.D. Amaral, et al., Trends Mol. Med. 15, 531 (2009) (Review), (5) J.D. Amaral, et al., J. Lipid. Res. 50, 1721 (2009) (Review), (6) M. Trauner, et al., Dig. Dis. 28, 220 (2010) (Review), (7) J.D. Amaral, et al., Curr. Pharm. Des. 16, 2493 (2010) (Review), (8) L. Serfaty, et al., Gastroenterol. Clin. Biol. 34, 516 (2010) (Review), (9) M.G. Roma, et al., Clin. Sci. (Lond). 121, 523 (2011) (Review)
InChi	InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
Quantity	5 g, 25 g, Bulk