An internal standard for the quantification of cholic acid
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Cholic Acid-d4

Item No. 20849

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-3α,7α,12α-trihydroxy-cholan-24-oic-2,2,4,4-d4 acid
CAS Number
116380-66-6
Synonyms
  • CA-d4
  • Cholalic Acid-d4
  • Cholalin-d4
Molecular Formula
C24H36D4O5
Formula Weight
412.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/ml
SMILES
O[C@@H]1C([2H])([2H])C[C@@]2(C)[C@@](C[C@@H](O)[C@]3([H])[C@]2([H])C[C@H](O)[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCC(O)=O)([H])C1([2H])[2H]
InChi Code
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1/i8D2,10D2
InChi Key
BHQCQFFYRZLCQQ-YFEOEUIKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Cholic acid-d4 is intended for use as an internal standard for the quantification of cholic acid (Item No. 20250) by GC- or LC-MS. Cholic acid is a primary bile acid.1 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; Item No. 20276) and taurocholic acid (TCA; Item No. 16215), respectively, in the liver, and is transformed into the secondary bile acid deoxycholic acid (DCA; Item No. 20756) by intestinal microbiota.1,2,3 It induces C. difficile colony formation in an agar dilution assay when used at a concentration of 0.1% w/v.4 Dietary administration of cholic acid (0.4% w/w) increases serum cholesterol levels, biliary phospholipid secretion, and fecal DCA levels in rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Šarenac, T.M., and Mikov, M. Bile acid synthesis: From nature to the chemical modification and synthesis and their applications as drugs and nutrients. Front. Pharmacol. 9, 939 (2018).

    2. Hunt, M.C., Siponen, M.I., and Alexson, S.E.H. The emerging role of acyl-CoA thioesterases and acyltransferases in regulating peroxisomal lipid metabolism. Biochim. Biophys. Acta 1822(9), 1397-1410 (2012).

    3. Staley, C., Weingarden, A.R., Khoruts, A., et al. Interaction of gut microbiota with bile acid metabolism and its influence on disease states. Appl. Microbiol. Biotechnol. 101(1), 47-64 (2017).

    4. Sorg, J.A., and Sonenshein, A.L. Bile salts and glycine as cogerminants for Clostridium difficile spores. J. Bacteriol. 190(7), 2505-2512 (2008).

    5. Uchida, K., Nomura, Y., and Takeuchi, N. 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. Biochem. 87(1), 187-194 (1980).

    Product Citations

    Qu, P., Rom, O., Li, K., et al. DT-109 ameliorates nonalcoholic steatohepatitis in nonhuman primates. Cell Metab. 35(5), 742-757 (2023).