A glycine-conjugated form of cholic acid
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Glycocholic Acid

Item No. 20276

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]-glycine
CAS Number
475-31-0
Synonyms
  • Cholylglycine
  • GCA
Molecular Formula
C26H43NO6
Formula Weight
465.6
Purity
≥95%
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[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C
InChi Code
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
InChi Key
RFDAIACWWDREDC-FRVQLJSFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Glycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid (Item No. 20250) and has roles in the emulsification of fats.1,2 It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml.3 Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin (Item No. 12091) in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin.4 It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases.3 Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lefebvre, P., Cariou, B., Lien, F., et al. Role of bile acids and bile acid receptors in metabolic regulation. Physiol. Rev. 89(1), 147-191 (2009).

    2. Guo, C., Xie, C., Ding, P., et al. Quantification of glycocholic acid in human serum by stable isotope dilution ultra performance liquid chromatography electrospray ionization tandem mass spectrometry. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1072, 315-319 (2018).

    3. Song, W.-S., Park, H.-M., Ha, J.M., et al. Discovery of glycocholic acid and taurochenodeoxycholic acid as phenotypic biomarkers in cholangiocarcinoma. Sci. Rep. 8(1), 11088 (2018).

    4. Lo, Y.L., Ho, C.T., and Tsai, F.L. Inhibit multidrug resistance and induce apoptosis by using glycocholic acid and epirubicin. Eur. J. Pharm. Sci. 35(1-2), 52-67 (2008).