A sphingolipid
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Labeled Version(s)
31199C16 Globotriaosylceramide-d9 (d18:1/16:0-d9)
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C16 Globotriaosylceramide (d18:1/16:0)

Item No. 24875

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]-hexadecanamide
CAS Number
137896-85-6
Synonyms
  • C16 Ceramide Trihexoside (d18:1/16:0)
  • Gb3 (d18:1/16:0)
  • N-Hexadecanoyl-ceramide trihexoside
Molecular Formula
C52H97NO18
Formula Weight
1024.3
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(CCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C52H97NO18/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(57)35(53-40(58)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-66-50-46(64)43(61)48(38(32-55)68-50)71-52-47(65)44(62)49(39(33-56)69-52)70-51-45(63)42(60)41(59)37(31-54)67-51/h27,29,35-39,41-52,54-57,59-65H,3-26,28,30-34H2,1-2H3,(H,53,58)/b29-27+/t35-,36+,37+,38+,39+,41-,42-,43+,44+,45+,46+,47+,48+,49-,50+,51+,52-/m0/s1
InChi Key
MGOOTGNGBOPVIV-VVNLPLDBSA-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

    C16 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from C16 lactosylceramide (Item No. 24352).1 C16 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes.2 It accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease.3 C16 globotriaosylceramide is also upregulated in plasma of patients with ovarian carcinoma compared to those with benign ovarian tumors or uterine fibroids.4 As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1528]

    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. 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).

    3. 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).

    4. Hou, Y., Li, J., Xie, H., et al. Differential plasma lipids profiling and lipid signatures as biomarkers in the early diagnosis of ovarian carcinoma using UPLC-MS. Metabolomics 12(18), (2015).