An internal standard for the quantification of ganglioside GM3
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Unlabeled Version(s)
15587Ganglioside GM3 (bovine brain) (sodium salt)
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C18 Ganglioside GM3-d3 (d18:1/18:0-d3) (ammonium salt, synthetic)

Item No. 39226

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[[O-(N-acetyl-α-neuraminosyl)-(2→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-octadecanamide-18,18,18-d3, monoammonium salt
CAS Number
2692623-85-9
Synonyms
  • C18 GM3-d3
  • N-ω-CD3-Octadecanoyl monosialoganglioside GM3
  • Monosialoganglioside GM3-d3
  • N-Stearoyl Monosialoganglioside GM3-d3
Molecular Formula
C59H104D3N2O21 • NH4
Formula Weight
1201.6
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solution in methanol
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): Soluble
SMILES
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@@]2([H])[C@@H]([C@@]([C@H]([C@H](O2)CO)O)([H])O[C@]3(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@@H]([C@H](O)CO)O)O3)O)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC([2H])([2H])[2H])=O.[NH4+]
InChi Code
InChI=1S/C59H108N2O21.H3N/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81-59)48(70)43(68)35-62;/h30,32,40-45,47-57,62-64,66-68,70-74H,4-29,31,33-38H2,1-3H3,(H,60,65)(H,61,69)(H,75,76);1H3/b32-30+;/t40-,41+,42-,43+,44+,45+,47+,48+,49-,50+,51+,52+,53+,54+,55-,56+,57-,59-;/m0./s1/i1D3;
InChi Key
WFQOHDPRXSLGNK-QICQTCFUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    C18 Ganglioside GM3-d3 (d18:1/18:0-d3) is intended for use as an internal standard for the quantification of ganglioside GM3 (Item No. 15587) by GC- or LC-MS. Ganglioside GM3 is a simple monosialoganglioside that demonstrates both antiproliferative and proapoptotic effects in tumor cells by modulating cell adhesion, proliferation, and differentiation.1,2 When used at a concentration of 20 μM, it suppresses angiogenesis and reduces endothelial cell proliferation and migration by inhibiting VEGFR2 and Akt phosphorylation.1 Furthermore, ganglioside GM3 has been shown to induce the dissociation of the insulin receptor-caveolin-1 complex from lipid microdomains, functioning as an inhibitor of insulin signaling and contributing to insulin resistance.3 This product is fully synthetic and has no variations in the fatty acyl chain or sphingoid backbone. It is intended for use as an analytical standard for the quantification of C18 Ganglioside GM3 by mass spectrometry.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mukherjee, P., Faber, A.C., Shelton, L.M., et al. Thematic review series: Sphingolipids. Ganglioside GM3 suppresses the proangiogenic effects of vascular endothelial growth factor and ganglioside GD1a. J. Lipid Res. 49(5), 929-938 (2008).

    2. Seyfried, T.N., and Mukherjee, P. Ganglioside GM3 is antiangiogenic in malignant brain cancer. J. Oncol. 961243 (2010).

    3. Kabayama, K., Sato, T., Saito, K., et al. Dissociation of the insulin receptor and caveolin-1 complex by ganglioside GM3 in the state of insulin resistance. Proc. Natl. Acad. Sci. USA 104(34), 13678-13683 (2007).