An internal standard for the quantification of glycoursodeoxycholic acid
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Glycoursodeoxycholic Acid-d4

Item No. 31309

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl-2,2,4,4-d4]-glycine
CAS Number
2044276-17-5
Synonyms
  • GUDCA-d4
  • Ursodeoxycholyl Glycine-d4
Molecular Formula
C26H39D4NO5
Formula Weight
453.7
Purity
≥99% deuterated forms (d1-d4)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
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-ODDJOPSVSA-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

    Glycoursodeoxycholic acid-d4 (GUDCA-d4) is intended for use as an internal standard for the quantification of GUDCA (Item No. 21698) by GC- or LC-MS. GUDCA is a glycine-conjugated form of the secondary bile acid ursodeoxycholic acid (UDCA; Item No. 15121).1,2 It has antioxidant effects in vitro in Barrett’s esophagus cells and primary cultured rat neurons.3,4 GUDCA reduces the levels of inflammatory cytokines and prevents cell death induced by unconjugated bilirubin (Item No. 17161) in an astroglial cell model of neonatal hyperbilirubinemia.5 Oral administration of GUDCA (500 mg/kg per day) decreases the severity of symptoms and increases the amount of A. muciniphila, a commensal bacterial species commonly decreased in patients with inflammatory bowel disease (IBD), in a mouse model of colitis.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. Van den Bossche, L., Hindryckx, P., Devisscher, L., et al. Ursodeoxycholic acid and its taurine- or glycine-conjugated species reduce colitogenic dysbiosis and equally suppress experimental colitis in mice. Appl. Environ. Microbiol. 83(7), e02766-02716 (2017).

    3. Goldman, A., Condon, A., Adler, E., et al. Protective effects of glycoursodeoxycholic acid in Barrett’s esophagus cells. Dis. Esophagus 23(2), 83-93 (2010).

    4. Brito, M.A., Lima, S., Fernandes, A., et al. Bilirubin injury to neurons: Contribution of oxidative stress and rescue by glycoursodeoxycholic acid. Neurotoxicology 29(2), 259-269 (2008).

    5. Fernandes, A., Vaz, A.R., Falcao, A.S., et al. Glycoursodeoxycholic acid and interleukin-10 modulate the reactivity of rat cortical astrocytes to unconjugated bilirubin. J. Neuropathol. Exp. Neurol. 66(9), 789-798 (2007).