An internal standard for the quantification of glycodeoxycholic acid
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Glycodeoxycholic Acid-d4

Item No. 31310

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3α,5β,12α)-3,12-dihydroxy-24-oxocholan-24-yl-2,2,4,4-d4]-glycine
CAS Number
1069132-37-1
Synonyms
  • GDCA-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)
Ethanol: slightly solubleMethanol: slightly soluble
SMILES
C[C@H](CCC(NCC(O)=O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C([2H])([2H])[C@H](O)C([2H])([2H])C[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C
InChi Code
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1/i10D2,12D2
InChi Key
WVULKSPCQVQLCU-JHVXYEQYSA-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

    Glycodeoxycholic acid-d4 is intended for use as an internal standard for the quantification of glycodeoxycholic acid (Item No. 20274) by GC- or LC-MS. Glycodeoxycholic acid (GDCA) is a glycine-conjugated form of the secondary bile acid deoxycholic acid (Item Nos. 18231 | 20756).1 It induces a reversible, concentration-dependent reduction in myogenic tone in rats and decreases expression of the gene encoding the cytochrome P450 (CYP) isoform 7A1 (CYP7A1) in rabbits.2,3 Serum levels of GDCA are elevated in non-surviving patients with acetaminophen-induced acute liver failure (AALF) compared with survivors.4 GDCA levels are also increased in the plasma of patients with asthma.5

    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. Khurana, S., Raina, H., Pappas, V., et al. Effects of deoxycholylglycine, a conjugated secondary bile acid, on myogenic tone and agonist-induced contraction in rat resistance arteries. PLoS One 7(2), e32006 (2012).

    3. Shang, Q., Guo, G.L., Honda, A., et al. Bile acid flux through portal but not peripheral veins inhibits CYP7A1 expression without involvement of ileal FGF19 in rabbits. Am. J. Physiol. Gastrointest. Liver Physiol. 307(4), G479-G486 (2014).

    4. Woolbright, B.L., McGill, M.R., Staggs, V.S., et al. Glycodeoxycholic acid levels as prognostic biomarker in acetaminophen-induced acute liver failure patients. Toxicol. Sci. 142(2), 436-444 (2014).

    5. Comhair, S.A.A., McDunn, J., Bennett, C., et al. Metabolomic endotype of asthma. J. Immunol. 195(2), 643-650 (2015).