A monosialylated ganglioside
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C18 Ganglioside GM1 (d18:1/18:0) (ammonium salt)

Item No. 42980

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[[O-β-D-galactopyranosyl-(1→3)-O-2-(acetylamino)-2-deoxy-β-D-galactopyranosyl-(1→4)-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, monoammonium salt
CAS Number
1329115-44-7
Synonyms
  • N-Octadecanoyl Monosialoganglioside GM1
  • N-Stearoyl-GM1
  • C18 GM1
  • GM1 (18:1/18:0)
  • GM1 (d18:1/C18:0)
  • N-Stearoyl Monosialoganglioside GM1
Molecular Formula
C73H130N3O31 • NH4
Formula Weight
1563.9
Purity
≥98%
Formulation (Request formulation change)
A solid
SMILES
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@@H]3O[C@@H]([C@@H]([C@@H]([C@H]3NC(C)=O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)CO)O[C@]5(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@@H]([C@H](O)CO)O)([H])O5)O)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC)=O.[NH4+]
InChi Code
InChI=1S/C73H131N3O31.H3N/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70;/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97);1H3/b33-31+;/t44-,45+,46-,47+,48+,49+,50+,51+,53+,54+,55+,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66+,67+,68-,69+,70-,71-,73-;/m0./s1
InChi Key
XKTKEUMFELHBSG-POYTVKKJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Ganglioside GM1 is a monosialylated ganglioside and the prototypic ganglioside for those containing one sialic acid residue.1,2 C18 Ganglioside GM1 is found in the brain, primarily in the piriform cortex, amygdala nucleus, striatum, and hippocampal CA1 region.3 The ratio of C18 ganglioside GM1 (d20:1/18:0) to C18 ganglioside GM1 (d18:1/18:0) is decreased in the outer molecular layer of the hippocampal dentate gyrus in postmortem tissue from patients with Alzheimer's disease.4 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1569]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kolter, T. Ganglioside biochemistry. ISRN Biochem. 506160 (2012).

    2. Mocchetti, I. Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins. Cell Mol. Life Sci. 62(19-20), 2283-2294 (2005).

    3. Andres, A.D., Young, L.E.A., Gentry, M.S., et al. Spatial profiling of gangliosides in mouse brain by mass spectrometry imaging. J. Lipid Res. 61(12), 1537 (2020).

    4. Hirano-Sakamaki, W., Sugiyama, E., Hayasaka, T., et al. Alzheimer’s disease is associated with disordered localization of ganglioside GM1 molecular species in the human dentate gyrus. FEBS Lett. 589(23), 3611-3616 (2015).