An internal standard for the quantification of glycochenodeoxycholic acid
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Glycochenodeoxycholic Acid-d4

Item No. 21890

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3α,5β,7α)-3,7-dihydroxy-24-oxocholan-24-yl-2,2,4,4-d4]-glycine
CAS Number
1201918-16-2
Synonyms
  • GCDCA-d4
Molecular Formula
C26H39D4NO5
Formula Weight
453.7
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/mlEthanol: 1 mg/ml
SMILES
C[C@H](CCC(NCC(O)=O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C([2H])([2H])[C@H](O)C([2H])([2H])C[C@]4(C)[C@@]3([H])CC[C@@]21C
InChi Code
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1/i8D2,12D2
InChi Key
GHCZAUBVMUEKKP-PKIQRPOYSA-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

    An internal standard for the quantification of glycochenodeoxycholic acid (GCDCA; Item No. 16942) by GC- or LC-MS. GCDCA is a glycine-conjugated form of the primary bile acid chenodeoxycholic acid (Item No. 10011286).1 It reduces formation of cholic acid (Item No. 20250) in primary human hepatocytes when used at a concentration of 100 µM.2 GCDCA (50, 75, and 100 µM) reduces the number of LC3 puncta, a marker of autophagy, and is cytotoxic to L-02 hepatocytes.1 GCDCA (50 µM) induces apoptosis in isolated rat hepatocytes, an effect that can be blocked by the protein kinase C (PKC) inhibitor chelerythrine (Item No. 11314).3 Fecal levels of GCDCA are decreased in a rat model of high-fat diet-induced obesity compared with rats fed a normal diet.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lan, W., Chen, Z., Chen, Y., et al. Glycochenodeoxycholic acid impairs transcription factor E3-dependent autophagy-lysosome machinery by disrupting reactive oxygen species homeostasis in L02 cells. Toxicol. Lett. 331, 11-21 (2020).

    2. Ellis, E., Axelson, M., Abrahamsson, A., et al. Feedback regulation of bile acid synthesis in primary human hepatocytes: Evidence that CDCA is the strongest inhibitor. Hepatology 38(4), 930-938 (2003).

    3. Gonzalez, B., Fisher, C., and Rosser, B.G. Glycochenodeoxycholic acid (GCDC) induced hepatocyte apoptosis is associated with early modulation of intracellular PKC activity. Mol. Cell. Biochem. 207(1-2), 19-27 (2000).

    4. Lin, H., An, Y., Tang, H., et al. Alterations of bile acids and gut microbiota in obesity induced by high fat diet in rat model. J. Agric. Food Chem. 67(13), 3624-3632 (2019).

    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).