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

CAS Number Unlabeled

81-25-4

CAS Number Unlabeled

81-25-4

Safety Information

WGK Germany 

3

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