A glycosphingolipid
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C24 Globotriaosylceramide (d18:1/24:0)

Item No. 45584

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]-tetracosanamide
CAS Number
82005-99-0
Synonyms
  • C24 Ceramide Trihexoside (d18:1/24:0)
  • Gb3 (d18:1/24:0)
  • N-Tetracosanoyl-ceramide trihexoside
Molecular Formula
C60H113NO18
Formula Weight
1136.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): Soluble
SMILES
O[C@@H]([C@@H](NC(CCCCCCCCCCCCCCCCCCCCCCC)=O)CO[C@H](O[C@@H]([C@H]([C@@H]1O)O[C@H](O[C@@H]([C@@H]([C@@H]2O)O[C@@H](O[C@@H]([C@@H]([C@@H]3O)O)CO)[C@@H]3O)CO)[C@@H]2O)CO)[C@@H]1O)/C=C/CCCCCCCCCCCCC
InChi Code
InChI=1S/C60H113NO18/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-48(66)61-43(44(65)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)42-74-58-54(72)51(69)56(46(40-63)76-58)79-60-55(73)52(70)57(47(41-64)77-60)78-59-53(71)50(68)49(67)45(39-62)75-59/h35,37,43-47,49-60,62-65,67-73H,3-34,36,38-42H2,1-2H3,(H,61,66)/b37-35+/t43-,44+,45+,46+,47+,49-,50-,51+,52+,53+,54+,55+,56+,57-,58+,59+,60-/m0/s1
InChi Key
MRVRZXMLIKCXOT-SHLWWNIASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $569

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    Product Description

    C24 Globotriaosylceramide (d18:1/24:0) is a glycosphingolipid found in mammalian cell membranes.1 It is the Pk antigen in the human P1PK blood group system.2 C24 Globotriaosylceramide (d18:1/24:0) acts as a receptor for Shiga and Shiga-like toxins in vitro and in vivo.3 It is a substrate of the enzyme α-galactosidase A that accumulates in endothelial, vascular smooth muscle, renal, epithelial, myocardial, and dorsal ganglia neuronal cells in Fabry disease, a lysosomal storage disorder characterized by a deficiency in α-galactosidase A.4 C24 Globotriaosylceramide (d18:1/24:0) mediates CD4-dependent fusion of HIV-1 with human erythrocyte cell membrane microdomains by binding HIV-1 glycoprotein 120 (gp120) and facilitates gp120-coreceptor interactions.5 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. Nicolaou, K.C., Caulfield, H., Kataoka, H., et al. A practical and enantioselective synthesis of glycosphingolipids and related compounds. Total synthesis of globotriaosylceramide (Gb3). J. Am. Chem. Soc. 110(23), 7910-7912 (1988).

    2. Naiki, M., and Marcus, D.M. Human erythrocyte P and Pk blood group antigens: Identification as glycosphingolipids. Biochem. Biophys. Res. Commun. 60(3), 1105-1111 (1974).

    3. Takeda, Y., Kurazono, H., and Yamasaki, S. Vero toxins (Shiga-like toxins) produced by enterohemorrhagic Escherichia coli (verocytotoxin-producing E. coli). Microbiol. Immunol. 37(8), 591-599 (1993).

    4. 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).

    5. Hammache, D., Yahi, N., Maresca, M., et al. Human erythrocyte glycosphingolipids as alternative cofactors for human immunodeficiency virus type 1 (HIV-1) entry: Evidence for CD4-induced interactions between HIV-1 gp120 and reconstituted membrane microdomains of glycosphingolipids (Gb3 and GM3). J. Virol. 73(6), 5244-5248 (1999).