An internal standard for the quantification of C16 globotriaosylceramide
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Unlabeled Version(s)
24875C16 Globotriaosylceramide (d18:1/16:0)
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C16 Globotriaosylceramide-d9 (d18:1/16:0-d9)

Item No. 31199

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-13,13,14,14,15,15,16,16,16-d9
CAS Number
2738376-84-4
Synonyms
  • C16 Ceramide Trihexoside (d18:1/16:0-d9)
  • Gb3 (d18:1/16:0-d9)
  • N-Hexadecanoyl-d9 (13,13,14,14,15,15,16,16,16)-ceramide Trihexoside
Molecular Formula
C52H88D9NO18
Formula Weight
1033.4
Purity
≥99% deuterated forms (d1-d9)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:DI water (2:1:0.2): soluble
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(CCCCCCCCCCCC([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=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/i2D3,4D2,6D2,8D2
InChi Key
MGOOTGNGBOPVIV-HQAVLLBJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $929

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    Product Description

    C16 Globotriaosylceramide-d9 (d18:1/16:0-d9) is intended for use as an internal standard for the quantification of C16 globotriaosylceramide (Item No. 24875) by GC- or LC-MS. C16 Globotriaosylceramide (d18:1/16:0) 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, a lysosomal storage disorder.3 Plasma levels of C16 globotriaosylceramide are increased in 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. 1551]

    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).