CAS Number474-25-9
SynonymsCDCA; Chenix; MFCD00064142; Chenodex; EINECS 207-481-8; Hekbilin; Fluibil; Ulmenide; Chenocol; chendol; Kebilis; anthropododesoxycholicacid; Chenodeoxycholic acid; 3α,7α-Dihydroxy-5β-cholanic Acid; Chendiol; 5β-Cholanic Acid-3α,7α-diol
Molecular FormulaC24H40O4
Molecular Weight392.57
Purity98%
Density1.1±0.1 g/cm3
Boiling Point547.1±25.0 °C at 760 mmHg
Melting Point165-167 °C (lit.)
Appearancepowder
EINECS207-481-8
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 474-25-9 |
| Catalog No. | 2A-9009715 |
| Chinese Name | 鹅去氧胆酸； 鹅脱氧胆酸 |
| Synonyms | CDCA; Chenix; MFCD00064142; Chenodex; EINECS 207-481-8; Hekbilin; Fluibil; Ulmenide; Chenocol; chendol; Kebilis; anthropododesoxycholicacid; Chenodeoxycholic acid; 3α,7α-Dihydroxy-5β-cholanic Acid; Chendiol; 5β-Cholanic Acid-3α,7α-diol |
| Molecular Formula | C24H40O4 |
| Molecular Weight | 392.57 |
| Purity | 98 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 547.1±25.0 °C at 760 mmHg |
| Melting Point | 165-167 °C (lit.) |
| Appearance | powder |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Storage Condition | Brown glass bottle airtightly packaged. Store at l |
| Application | Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates the nuclear receptor FXR, which is involved in cholesterol metabolism. |
| EINECS | 207-481-8 |
| HTC | 2918990090 |
| PubChem ID | 24893153 |
| MDL Number | MFCD00064142 |
| SMILES | C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| 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 |
| InChI Key | RUDATBOHQWOJDD-BSWAIDMHSA-N |
| Beilstein/REAXYS | 3219887 |
| NACRES Code | NA.25 |
| UNSPSC | 12352106 |
| Hazard Symbols | Transport |
| MSDS | msds/9715_1_474_25_9.pdf |
| Bioactivity | Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> FXR Natural Products >> Acids and Aldehydes Research Areas >> Metabolic Disease Target Human Endogenous Metabolite In Vitro Chenodeoxycholic acid (CDCA) and Deoxycholic acid (DCA) both inhibit 11 beta HSD2 with IC50 values of 22 mM and 38 mM, respectively and causes cortisol-dependent nuclear translocation and increases transcriptionalactivity of mineralocorticoid receptor (MR)[1]. Chenodeoxycholic acid is able to stimulate Ishikawa cell growth by inducing a significant increase in Cyclin D1 protein and mRNA expression through the activation of the membrane G protein-coupled receptor (TGR5)-dependent pathway[2]. Chenodeoxycholic acid (CDCA) induces LDL receptor mRNA levels approximately 4 fold and mRNA levels for HMG-CoA reductase and HMG-CoA synthase two fold in a cultured human hepatoblastoma cell line, Hep G2[3]. Chenodeoxycholic acid-induced Isc is inhibited (≥67%) by Bumetanide, BaCl2, and the cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor CFTRinh-172. Chenodeoxycholic acid-stimulated Isc is decreased 43% by the adenylate cyclase inhibitor MDL12330A and Chenodeoxycholic acid increases intracellular cAMP concentration[4]. Chenodeoxycholic acid treatment activates C/EBPβ, as shown by increases in its phosphorylation, nuclear accumulation, and expression in HepG2 cells. Chenodeoxycholic acid enhances luciferase gene transcription from the construct containing -1.65-kb GSTA2 promoter, which contains C/EBP response element (pGL-1651). Chenodeoxycholic acid treatment activates AMP-activated protein kinase (AMPK), which leads to extracellular signal-regulated kinase 1/2 (ERK1/2) activation, as evidenced by the results of experiments using a dominant-negative mutant of AMPKα and chemical inhibitor[5]. Kinase Assay Briefly, transfected HEK-293 cells, incubated in charcoal-treated Dulbecco's modified Eagle's medium for 24 h, are washed once with Hanks' solution and resuspended in a buffer containing 100 mM NaCl, 1 mM MgCl2, 1 mM EDTA, 1 mM EGTA, 250 mMsucrose, 20 mM Tris-HCl, pH 7.4. Cells are lysed by freezing in liquid nitrogen. Dehydrogenase activity is measured in a final volume of 20 μL containing the appropriate concentration of bile acid, 30 nCi of [3H]cortisol, and unlabeled cortisol to a final concentrations of 50 nM. The reaction is started by mixing cell lysate with the reaction mixture. Alternatively, endoplasmic reticulum microsomes are prepared from transfected HEK-293 cells and incubated with reaction mixture containing various concentrations of cortisol and CDCA. Incubation proceeded for 20 min, and the conversion of cortisol to cortisone is determined by thin layer chromatography (TLC). Because of the inaccuracy of the TLC method at low conversion rates and the end-product inhibition of 11βHSD2 at conversion rates higher than 60-70%, only conversion rates between 10 and 60% are considered for calculation. The inhibitory constant IC50 is evaluated using the curve-fitting program. Results are expressed as means±S.E. and consist of at least four independent measurements. Cell Assay The cell viability is analyzed by incubating transfected HEK-293 cells and CHO cells for 1 h with the corresponding concentration of bile acid and staining with trypan blue. The toxicity of bile acids is analyzed using the tetrazolium salt MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) according to the cell proliferation kit I. No significant differences between control and bile acid-treated cells are obtained in both tests. References [1]. Stauffer AT, et al. Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor. J Biol Chem. 2002 Jul 19;277(29):26286-92 [2]. Casaburi I, et al. Chenodeoxycholic acid through a TGR5-dependent CREB signaling activation enhances cyclin D1 expression and promotes human endometrial cancer cell proliferation. Cell Cycle. 2012 Jul 15;11(14):2699-710 [3]. Kawabe Y, et al. The molecular mechanism of the induction of the low density lipoprotein receptor by chenodeoxycholic acid in cultured human cells. Biochem Biophys Res Commun. 1995 Mar 8;208(1):405-11. [4]. Ao M, et al. Chenodeoxycholic acid stimulates Cl(-) secretion via cAMP signaling and increases cystic fibrosis transmembrane conductance regulator phosphorylation in T84 cells. Am J Physiol Cell Physiol. 2013 Aug 15;305(4):C447-56 [5]. Noh K, et al. Farnesoid X receptor activation by chenodeoxycholic acid induces detoxifying enzymes through AMP-activated protein kinase and extracellular signal-regulated kinase 1/2-mediated phosphorylation of CCAAT/enhancer binding protein β. Drug Metab Chemical & Physical Properties Density 1.1±0.1 g/cm3 Boiling Point 547.1±25.0 °C at 760 mmHg Melting Point 165-167 °C(lit.) Molecular Formula C24H40O4 Molecular Weight 392.572 Flash Point 298.8±19.7 °C Exact Mass 392.292664 PSA 77.76000 LogP 4.66 Vapour Pressure 0.0±3.3 mmHg at 25°C Index of Refraction 1.543 InChIKey RUDATBOHQWOJDD-BSWAIDMHSA-N SMILES CC(CCC(=O)O)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C Water Solubility PRACTICALLY INSOLUBLE |
| Use of | Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. Properties Articles130 Name chenodeoxycholic acid Synonym More Synonyms Chenodeoxycholic acid Biological Activity Description Chenodeoxycholic Acid is a hydrophobic primary bile acid that activates nuclear receptors (FXR) involved in cholesterol metabolism. Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> FXR Natural Products >> Acids and Aldehydes Research Areas >> Metabolic Disease Human Endogenous Metabolite References [1]. Stauffer AT, et al. Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor. J Biol Chem. 2002 Jul 19;277(29):26286-92 [2]. Casaburi I, et al. Chenodeoxycholic acid through a TGR5-dependent CREB signaling activation enhances cyclin D1 expression and promotes human endometrial cancer cell proliferation. Cell Cycle. 2012 Jul 15;11(14):2699-710 [3]. Kawabe Y, et al. The molecular mechanism of the induction of the low density lipoprotein receptor by chenodeoxycholic acid in cultured human cells. Biochem Biophys Res Commun. 1995 Mar 8;208(1):405-11. Chemical & Physical Properties Molecular Formula C24H40O4 Exact Mass 392.292664 PSA 77.76000 Index of Refraction 1.543 InChIKey RUDATBOHQWOJDD-BSWAIDMHSA-N Water Solubility PRACTICALLY INSOLUBLE |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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