A sphingolipid
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Labeled Version(s)
24626C18 Globotriaosylceramide-d3 (d18:1/18:0-d3)
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C18 Globotriaosylceramide (d18:1/18:0)

Item No. 24877

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[[(O-α-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl)oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-octadecanamide
CAS Number
69283-33-6
Synonyms
  • C18 Ceramide Trihexoside (d18:1/18:0)
  • Gb3(d18:1/18:0)
  • N-Octadecanoyl-ceramide trihexoside
Molecular Formula
C54H101NO18
Formula Weight
1052.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): SolubleDMSO: SolubleMethanol: Warmed
SMILES
O[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@H](O[C@]3([H])[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O3)[C@H](O)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@H](NC(CCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C54H101NO18/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(60)55-37(38(59)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-68-52-48(66)45(63)50(40(34-57)70-52)73-54-49(67)46(64)51(41(35-58)71-54)72-53-47(65)44(62)43(61)39(33-56)69-53/h29,31,37-41,43-54,56-59,61-67H,3-28,30,32-36H2,1-2H3,(H,55,60)/b31-29+/t37-,38+,39+,40+,41+,43-,44-,45+,46+,47+,48+,49+,50+,51-,52+,53+,54-/m0/s1
InChi Key
KWGVNZWSEWAOMI-DHCJWVHISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $569

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    Product Description

    C18 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from lactosylceramide (Item No. 16983).1 It inhibits aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate (PMA; 10008014) when used at a concentration of 1 μM.2 C18 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes.3 It accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A.4 C18 globotriaosylceramide also accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease.5 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1529]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lingwood, C.A., and Branch, D.R. The role of glycosphingolipids in HIV/AIDS. Discov. Med. 11(59), 303-313 (2011).

    2. Fiore, S., Nicolaou, K.C., Caulfield, T., et al. Evaluation of synthetic sphingosine, lysosphingolipids and glycosphingolipids as inhibitors of functional responses of human neutrophils. Biochem. J. 266(1), 25-31 (1990).

    3. Hoffmann, P., Hülsewig, M., Duvar, S., et al. On the structural diversity of Shiga toxin glycosphingolipid receptors in lymphoid and myeloid cells determined by nanoelectrospray ionization tandem mass spectrometry. Rapid Commun. Mass. Spectrom. 24(15), 2295-2304 (2010).

    4. Kamani, M.A., Provençal, P., Boutin, M., et al. Glycosphingolipid storage in Fabry mice extends beyond globotriaosylceramide and is affected by ABCB1 depletion. Future Sci. OA. 2(4), FS0147 (2016).

    5. Feldt-Rasmussen, U., Rasmussen, A.K., Mersebach, H., et al. Fabry disease: A new challenge in endocrinology and metabolism? Eur. J. Endocrinol. 146(6), 741-742 (2002).