Specifications
- Purity
- ≥99% (T)
- Appearance
- White to off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- ethanol, DMSO
- Melting Point
- 203-204 °C (lit.)
Category: Lipids, Fatty Acids
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.
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 |