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Chenodeoxycholic Acid
Cayman Chemical Item Number 10011286
Description
Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.1↗ They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress.2↗,3↗ Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis. Chenodeoxycholic acis (CDCA) is a hydrophobic primary bile acid that activates nuclear receptors involved in cholesterol metabolism.3↗,4↗ EC50 concentrations for activation of FXR range from 13-34 μM.5↗,6↗ In cells, CDCA also binds to bile acid binding proteins (BABP) with a reported stiochiometery of 1:2.4↗ CDCA toxicity is linked to increased cellular glutathione levels and increased oxidative stress. Exposure of cells to excess CDCA contributes to liver and intestinal cancers.3↗
Synonyms CDCA,Fluibil,Hekbilin,Anthropodeoxycholic Acid,Kebilis,Ulmenide
Formal Name 3α,7α-dihydroxy-5β-cholan-24-oic acid
CAS Number 474-25-9
Molecular Formula C24H40O4
Formula Weight 392.6
Formulation A crystalline solid
Purity ≥95%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES C[C@@]12[C@](CC[C@]2([H])[C@H](C)CCC(O)=O)([H])C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC1
InCHI Code 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
InCHI Key RUDATBOHQWOJDD-LIPUCWBFSA-N |