An internal standard for the quantification of ursodeoxycholic acid
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Ursodeoxycholic Acid-d4

Item No. 21892

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β,7β)-3,7-dihydroxy-cholan-24-oic-2,2,4,4-d4 acid
CAS Number
347841-46-7
Synonyms
  • UDCA-d4
Molecular Formula
C24H36D4O4
Formula Weight
396.6
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
OC(CC[C@@H](C)[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)=O
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-QGCKUCIHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Ursodeoxycholic acid-d4 (UDCA-d4) is intended for use as an internal standard for the quantification of UDCA (Item No. 15121) by GC- or LC-MS. UDCA is a secondary bile acid formed via epimerization of chenodeoxycholic acid (CDCA; Item No. 10011286).1,2 UDCA is also a metabolite of lithocholic acid (LCA; Item No. 20253) in human liver microsomes.3 It inhibits taurocholic acid (Item No. 16215) uptake in HeLa cells expressing recombinant sodium/taurocholate cotransporting polypeptide (NTCP) with an IC50 value of 3.6 μM.4 UDCA (50 μM) inhibits apoptosis induced by deoxycholic acid (DCA; Item Nos. 20756 | 18231) or ethanol in primary rat hepatocytes.5 Dietary administration of UDCA blocks DCA-induced increases in the number of TUNEL-positive hepatocytes in rats. Formulations containing UDCA have been used in the treatment of primary biliary cirrhosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dawson, P.A., and Karpen, S.J. Intestinal transport and metabolism of bile acids. J. Lipid Res. 56(6), 1085-1099 (2015).

    2. Chiang, J.Y.L. Bile acid metabolism and signaling in liver disease and therapy. Liver Res. 1(1), 3-9 (2017).

    3. Deo, A.K., and Bandiera, S.M. 3-Ketocholanoic acid is the major in vitro human hepatic microsomal metabolite of lithocholic acid. Drug Metab. Dispos. 37(9), 1938-1947 (2009).

    4. Kim, R.B., Leake, B., Cvetkovic, M., et al. Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J. Pharmacol. Exp. Ther. 291(3), 1204-1209 (1999).

    5. Rodrigues, C.M.P., Fan, G., Ma, X., et al. A novel role for ursodeoxycholic acid in inhibiting apoptosis by modulating mitochondrial membrane perturbation. J. Clin. Invest. 101(12), 2790-2799 (1998).