A ganglioside
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Ganglioside GM2 (bovine brain) (sodium salt)

Item No. 27192

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
19600-01-2
Synonyms
  • GM2
  • Monosialoganglioside GM2
Molecular Formula
C67H120N3O26 • Na (for stearoyl)
Formula Weight
1383.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): solubleWater: 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[C@]3([H])O[C@@H]([C@@H]([C@@H]([C@H]3NC(C)=O)O)O)CO)([H])O[C@]4(C([O-])=O)C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@@H]([C@H](O)CO)O)([H])O4)O)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC)=O.[Na+]
InChi Code
InChI=1S/C67H121N3O26.Na/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-50(80)70-43(44(77)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-89-64-57(85)56(84)59(48(38-73)91-64)93-65-58(86)62(60(49(39-74)92-65)94-63-52(69-42(4)76)55(83)54(82)47(37-72)90-63)96-67(66(87)88)35-45(78)51(68-41(3)75)61(95-67)53(81)46(79)36-71;/h31,33,43-49,51-65,71-74,77-79,81-86H,5-30,32,34-40H2,1-4H3,(H,68,75)(H,69,76)(H,70,80)(H,87,88);/q;+1/p-1/b33-31+;/t43-,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60-,61+,62+,63-,64+,65-,67-;/m0./s1
InChi Key
YZCIBJIDUSQSAE-VUDKKWOPSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $321

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    1 mg

    $576

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    Product Description

    Ganglioside GM2 is a glycosphingolipid component of cellular membranes, primarily the plasma membrane.1 Gangliosides isolated from apoptogenic glioblastoma multiforme (GBM) cells are enriched in ganglioside GM2 compared with nonapoptogenic GBM cells, and ganglioside GM2 induces activated T cell death when used at a concentration of 150 μg/ml in vitro.2 Serum ganglioside GM2 levels are increased in patients with breast cancer or cholangiocarcinoma.3,4 Levels of ganglioside GM2 are elevated in the brain of patients with Sandhoff disease, as well as feline and mouse models of the disease.5 Ganglioside GM2 accumulates in the lysosomes of individuals with Tay-Sachs disease and GM2-activator deficiency, as well as in the CNS of patients with and animal models of mucopolysaccharide storage disorders and Niemann-Pick disease types A, C1, and C2.5,6 This product contains ganglioside GM2 molecular species with primarily C18:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bisel, B., Pavone, F.S., and Calamai, M. GM1 and GM2 gangliosides: Recent developments. Biomol Concepts 5(1), 87-93 (2014).

    2. Chahlavi, A., Rayman, P., Richmond, A.L., et al. Glioblastomas induce T-lymphocyte death by two distinct pathways involving gangliosides and CD70. Cancer Res. 65(12), 5428-5438 (2005).

    3. Li, Q., Sun, M., Yu, M., et al. Gangliosides profiling in serum of breast cancer patient: GM3 as a potential diagnostic biomarker. Glycoconj. J. 36(5), 419-428 (2019).

    4. Talabnin, K., Talabnin, C., Kumagai, T., et al. Ganglioside GM2: A potential biomarker for cholangiocarcinoma. J. Int. Med. Res. 48(7), 1-10 (2020).

    5. Baek, R.C., Martin, D.R., Cox, N.R., et al. Comparative analysis of brain lipids in mice, cats, and humans with Sandhoff disease. Lipids 44(3), 197-205 (2009).

    6. Walkley, S.U. Secondary accumulation of gangliosides in lysosomal storage disorders. Semin. Cell Dev. Biol. 15(4), 433-444 (2004).