An internal standard for the quantification of chenodeoxycholic acid
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Chenodeoxycholic Acid-d4

Item No. 20848

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3α,7α-dihydroxy-5β-cholan-24-oic-2,2,4,4-d4 acid
CAS Number
99102-69-9
Synonyms
  • CDCA-d4
Molecular Formula
C24H36D4O4
Formula Weight
396.6
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])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@H](C)CCC(O)=O)([H])C1([2H])[2H]
InChi Code
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/i8D2,12D2
InChi Key
RUDATBOHQWOJDD-PSTGXAJBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Chenodeoxycholic acid-d4 (CDCA-d4) is intended for use as an internal standard for the quantification of CDCA (Item No. 10011286) by GC- or LC-MS. CDCA is a hydrophobic primary bile acid.1 It is formed from cholesterol in the liver via a multistep process catalyzed by the cytochrome P450 (CYP) isoforms CYP7A1, CYP8B1, and CYP27A1. CDCA is a farnesoid X receptor (FXR) agonist that binds to FXRs in a TR-FRET assay (EC50 = 13 µM) and induces FXR transactivation in a reporter assay.2,3 It induces transcription of the gene encoding the Nrf2 target glutamate cysteine ligase (GCL) in primary hepatocytes and HepG2 cells when used at concentrations ranging from 25 to 100 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fiorucci, S., and Distrutti, E. Chenodeoxycholic acid: An update on its therapeutic applications. Bile acids and their receptors. Handbook of experimental pharmacology 256, 265-282 (2019).

    2. Ohinata, Y., Payer, B., O'Carroll, D., et al. Blimp1 is a critical determinant of the germ cell lineage in mice. Nature 436(7048), 207-213 (2005).

    3. Urizar, N.L., Liverman, A.B., Dodds, D.T., et al. A natural product that lowers cholesterol as an antagonist ligand for FXR. Science 296(5573), 1703-1706 (2002).

    4. Tan, K.P., Yang, M., and Ito, S. Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. Mol. Pharmacol. 72(5), 1380-1390 (2007).

    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).