Chenodeoxycholic Acid

Cayman Chemical Item Number 10011286

CDCA; Fluibil; Hekbilin; Anthropodeoxycholic Acid; Kebilis; Ulmenide (CAS 474-25-9)

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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

1. Makishima, M., Okamoto, A.Y., Repa, J.J., et al. Identification of a nuclear receptor for bile acids. Science 284 1362-1365 (1999).

2. Barbier, O., Torra, I.P., Sirvent, A., et al. FXR induces the UGT2B4 enzyme in hepatocytes: A potential mechanism of negative feedback control of FXR activity. Gastroenterology 124 1926-1940 (2003).

3. Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol Pharmacol 72(5) 1380-1390 (2007).

4. Eliseo, T., Ragona, L., Catalano, M., et al. Structural and dynamic determinants of ligand binding in the ternary complex of chicken liver bile acid binding protein with two bile salts revealed by NMR. Biochemistry 46(44) 12557-12567 (2007).

5. Urizar, N.L., Liverman, A.B., Dodds, D.T., et al. A natural product that lowers cholesterol as an anatagonist ligand for FXR.. Science 296 1703-1706 (2002).

6. Glickman, J.F., Wu, X., Mercuri, R., et al. A comparison of ALPHAScreen, TR-FRET, and TRF as assay methods for FXR nuclear receptors. J Biomol Screen 7(1) 3-10 (2002).

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
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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
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​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
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RUDATBOHQWOJDD-LIPUCWBFSA-N

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Size Price Quantity Subtotal
1 g $10.00 $0.00
5 g $45.00 $0.00
10 g $80.00 $0.00
25 g $175.00 $0.00
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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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