Chenodeoxycholic Acid

• CAT Number: A001094
• CAS Number: 474-25-9
• Molecular Formula: C24H40O4
• Molecular Weight: 392.60
• Purity: ≥95%
• Synonyms: Chenodiol
• Target: FXR
• Solubility: >13.1mg/mL in DMSO
• Storage: 3 years -20C powder
• IUPAC Name: (4R)-4-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• 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
• InChIKey: RUDATBOHQWOJDD-BSWAIDMHSA-N
• SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C

Chenodeoxycholic Acid (Cat No.:A001094) is a primary bile acid produced in the liver and essential for digestion and absorption of fats. It emulsifies dietary fats, aiding their breakdown and absorption in the small intestine. CDCA is used therapeutically to dissolve cholesterol gallstones and treat certain liver disorders, including cerebrotendinous xanthomatosis, by reducing cholesterol synthesis. Its role in regulating bile acid synthesis has also led to interest in metabolic and digestive health research, positioning CDCA as valuable in exploring therapies for gallbladder, liver, and cholesterol-related conditions.

Reference

1:Chenodeoxycholic acid stimulated fibroblast growth factor 19 response – a potential biochemical test for bile acid diarrhoea. Borup C, Wildt S, Rumessen JJ, Bouchelouche PN, Graff J, Damgaard M, McQuitty C, Rainteau D, Munck LK.Aliment Pharmacol Ther. 2017 Jun;45(11):1433-1442. doi: 10.1111/apt.14056. Epub 2017 Apr 5. PMID: 28378364
2:Chenodeoxycholic Acid Derivative HS-1200 Inhibits Hepatocarcinogenesis and Improves Liver Function in Diethylnitrosamine-Exposed Rats by Downregulating MTH1. Xu M, Zhao Q, Shao D, Liu H, Qi J, Qin C.Biomed Res Int. 2017;2017:1465912. doi: 10.1155/2017/1465912. Epub 2017 Feb 5. PMID: 28261604 Free PMC Article
3:Chenodeoxycholic acid stimulates glucagon-like peptide-1 secretion in patients after Roux-en-Y gastric bypass. Nielsen S, Svane MS, Kuhre RE, Clausen TR, Kristiansen VB, Rehfeld JF, Holst JJ, Madsbad S, Bojsen-Moller KN.Physiol Rep. 2017 Feb;5(3). pii: e13140. doi: 10.14814/phy2.13140. Epub 2017 Feb 14. PMID: 28202805 Free PMC Article
4:Treatment with the natural FXR agonist chenodeoxycholic acid reduces clearance of plasma LDL whilst decreasing circulating PCSK9, lipoprotein(a) and apolipoprotein C-III. Ghosh Laskar M, Eriksson M, Rudling M, Angelin B.J Intern Med. 2017 Jun;281(6):575-585. doi: 10.1111/joim.12594. Epub 2017 Feb 1. PMID: 28145001
5:Chenodeoxycholic acid activates NLRP3 inflammasome and contributes to cholestatic liver fibrosis. Gong Z, Zhou J, Zhao S, Tian C, Wang P, Xu C, Chen Y, Cai W, Wu J.Oncotarget. 2016 Dec 20;7(51):83951-83963. doi: 10.18632/oncotarget.13796. PMID: 27924062 Free PMC Article
6:Chenodeoxycholic acid requires activation of EGFR, EPAC, and Ca2+ to stimulate CFTR-dependent Cl- secretion in human colonic T84 cells. Domingue JC, Ao M, Sarathy J, Rao MC.Am J Physiol Cell Physiol. 2016 Nov 1;311(5):C777-C792. doi: 10.1152/ajpcell.00168.2016. Epub 2016 Aug 24. PMID: 27558159
7:Prolonged fibroblast growth factor 19 response in patients with primary sclerosing cholangitis after an oral chenodeoxycholic acid challenge. Zweers SJ, de Vries EM, Lenicek M, Tolenaars D, de Waart DR, Koelfat KV, Groen AK, Olde Damink SW, Beuers U, Ponsioen C, Jansen PL, Schaap FG.Hepatol Int. 2017 Jan;11(1):132-140. doi: 10.1007/s12072-016-9769-7. Epub 2016 Sep 30. PMID: 27696157 Free PMC Article
8:The bile acid chenodeoxycholic acid directly modulates metabolic pathways in white adipose tissue in vitro: insight into how bile acids decrease obesity. Teodoro JS, Rolo AP, Jarak I, Palmeira CM, Carvalho RA.NMR Biomed. 2016 Oct;29(10):1391-402. doi: 10.1002/nbm.3583. Epub 2016 Aug 4. PMID: 27488269
9:Protoscolicidal effects of chenodeoxycholic acid on protoscoleces of Echinococcus granulosus. Shi H, Lei Y, Wang B, Wang Z, Xing G, Lv H, Jiang Y.Exp Parasitol. 2016 Aug;167:76-82. doi: 10.1016/j.exppara.2016.05.004. Epub 2016 May 17. PMID: 27207732
10:Chenodeoxycholic acid significantly impacts the expression of miRNAs and genes involved in lipid, bile acid and drug metabolism in human hepatocytes. Krattinger R, Boström A, Lee SM, Thasler WE, Schiöth HB, Kullak-Ublick GA, Mwinyi J.Life Sci. 2016 Jul 1;156:47-56. doi: 10.1016/j.lfs.2016.04.037. Epub 2016 May 10. PMID: 27174168 Free Article