ChemicalBook Product Catalog Chemical Reagents Deuterated Reagents CHOLIC-2,2,4,4-D4 ACID

CHOLIC-2,2,4,4-D4 ACID

Product NameCHOLIC-2,2,4,4-D4 ACID
CAS116380-66-6
MFC24H36D4O5
MW412.6
EINECS
MOL File116380-66-6.mol

Chemical Properties

Melting point	200-201°C (lit.)
storage temp.	Store at -20°C
solubility	DMF: 30 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 20 mg/ml,Ethanol: 20 mg/ml
form	Solid
color	White to Off-White
InChIKey	BHQCQFFYRZLCQQ-XJNZYMKVNA-N
SMILES	[2H]C1([2H])C[C@]2(C)[C@H]3C[C@H](O)[C@]4(C)[C@H](CC[C@H]4[C@@H]3[C@H](O)C[C@@H]2C([2H])([2H])[C@@H]1O)[C@H](C)CCC(O)=O
CAS Number Unlabeled	81-25-4

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Cholic acid-d₄ is intended for use as an internal standard for the quantification of cholic acid by GC- or LC-MS. Cholic acid is a primary bile acid. It is formed from cholesterol via a multistep process catalyzed by the cytochrome P450 (CYP) isoforms CYP7A1, CYP8B1, and CYP27A1. Cholic acid is conjugated to glycine or taurine by bile acid-CoA:amino acid N-acyltransferase (BAAT) to produce glycocholic acid (GCA; ) and taurocholic acid (TCA; ), respectively, in the liver, and is transformed into the secondary bile acid deoxycholic acid (DCA; ) by intestinal microbiota. It induces C. difficile colony formation in an agar dilution assay when used at a concentration of 0.1% w/v. Dietary administration of cholic acid (0.4% w/w) increases serum cholesterol levels, biliary phospholipid secretion, and fecal DCA levels in rats.

Uses

Cholic Acid-d4 is a labelled analog of Cholic acid (C432600) which is a choleretic produced by, and isolated from liver cells.

Definition

ChEBI: Cholic acid-2,2,4,4-d4 is a bile acid.

References

[1] TANJA M ARENAC Momir M. Bile Acid Synthesis: From Nature to the Chemical Modification and Synthesis and Their Applications as Drugs and Nutrients.[J]. Frontiers in Pharmacology, 2018: 939. DOI: 10.3389/fphar.2018.00939
[2] MARY C. HUNT Stefan E H A Marina I Siponen. The emerging role of acyl-CoA thioesterases and acyltransferases in regulating peroxisomal lipid metabolism[J]. Biochimica et biophysica acta. Molecular basis of disease, 2012, 1822 9: Pages 1397-1410. DOI: 10.1016/j.bbadis.2012.03.009
[3] CHRISTOPHER STALEY. Interaction of gut microbiota with bile acid metabolism and its influence on disease states[J]. Applied Microbiology and Biotechnology, 2016, 101 1: 47-64. DOI: 10.1007/s00253-016-8006-6
[4] JOSEPH A SORG A L S. Bile salts and glycine as cogerminants for Clostridium difficile spores.[J]. Journal of Bacteriology, 2008: 2505-2512. DOI: 10.1128/jb.01765-07
[5] K UCHIDA N T Y Nomura. Effects of cholic acid, chenodeoxycholic acid, and their related bile acids on cholesterol, phospholipid, and bile acid levels in serum, liver, bile, and feces of rats.[J]. Journal of biochemistry, 1980, 87 1: 187-194. DOI: 10.1093/oxfordjournals.jbchem.a132724
[6] PENGXIANG QU. DT-109 ameliorates nonalcoholic steatohepatitis in nonhuman primates.[J]. Cell metabolism, 2023, 35 5: 742-757.e10. DOI: 10.1016/j.cmet.2023.03.013

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