A sphingolipid
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Ganglioside GM4 (chicken egg) (ammonium salt)

Item No. 24851

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
ganglioside GM4, monoammonium salt
Synonyms
  • Ganglioside G7
  • Monosialoganglioside GM4
Molecular Formula
C57H106N2O17 • NH3 (for 2-hydroxydocosanoyl)
Formula Weight
1108.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): SolubleChloroform:Methanol (2:1): soluble
SMILES
O[C@H]1[C@@](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC([R])=O)([H])O[C@H](CO)[C@H](O)[C@]1([H])O[C@]2(C(O)=O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@@H]([C@H](O)CO)O)O2.N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $602

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    Product Description

    Ganglioside GM4 is a sialic acid-containing glycosphingolipid found primarily in the brain of mammals, particularly in human myelin.1 Ganglioside GM4 is also found on epithelial cells in the intestinal tract of the red sea bream where it is an attachment site for Gram-negative Vibrios, the bacteria that causes vibriosis in humans after ingestion of raw or undercooked seafood.2 Ganglioside GM4 species have been found as 11 out of 61 gangliosides detected in an adrenal neuroblastoma tumor.3 Administration of ganglioside GM4 (80 and 160 µg) prevents development of myelin basic protein-induced experimental autoimmune encephalomyelitis (EAE) in guinea pigs.4 This product contains ganglioside GM4 molecular species with primarily 2-hydroxy C22:0, 2-hydroxy C24:0, and 2-hydroxy C23:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1535]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ueno, K., Ando, s., and Yu, R.K. Gangliosides of human, cat, and rabbit spinal cords and cord myelin. J. Lipid Res. 19(7), 863-871 (1978).

    2. Chisada, S., Shimizu, K., Kamada, H., et al. Vibrios adhere to epithelial cells in the intestinal tract of red sea bream, Pagrus major, utilizing GM4 as an attachment site. FEMS Microbiol. Lett. 341(1), 18-26 (2013).

    3. Robu, A.C., Vukelić, Ž., Schiopu, C., et al. Mass spectrometry of gangliosides in extracranial tumors: Application to adrenal neuroblastoma. Anal. Biochem. 509, 1-11 (2016).

    4. Mullin, B.R., Patrick, D.H., Poore, C.M., et al. Prevention of experimental allergic encephalomyelitis by ganglioside GM4. Brain Res. 296(1), 174-176 (1984).