A bioactive sphingolipid
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Galactosylsphingosine (d18:1)

Item No. 20338

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2S-amino-3R-hydroxy-4E-octadecen-1-yl-β-D-galactopyranoside
CAS Number
2238-90-6
Synonyms
  • Galactosylsphingosine
  • Psychosine
Molecular Formula
C24H47NO7
Formula Weight
461.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (5:1): solubleEthanol: >1 mg/mlPBS (pH 7.2): >1 mg/ml
SMILES
O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)N
InChi Code
InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1
InChi Key
HHJTWTPUPVQKNA-PIIMIWFASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $70

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    5 mg

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    10 mg

    $369

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    Product Description

    Galactosylsphingosine is a bioactive sphingolipid.1,2,3 It potentiates LPS-induced production of inflammatory cytokines, decreases the mitochondrial membrane potential, and induces cell death in mouse astrocytes, effects that can be reversed by the sphingosine-1-phosphate receptor agonist FTY720 phosphate (Item No. 10008639).1 Galactosylsphingosine (0.1 and 1 µM) induces demyelination of mouse cerebellar slices. It inhibits PDGF-induced translocation of PKC to the cell surface and induces apoptosis in MO3.13 oligodendrocytes.4 Galactosylsphingosine (10 and 15 µM) inhibits gene transcription mediated by peroxisome proliferator-activated receptor α (PPARα) in reporter assays using C6 glial cells.5 Levels of galactosylsphingosine are increased in postmortem brain from patients with Krabbe disease, a lysosomal storage disorder characterized by a β-galactosylceramidase deficiency.1,2,3,5[Matreya, LLC. Catalog No. 1305]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. O'Sullivan, C., and Dev, K.K. Galactosylsphingosine (psychosine)-induced demyelination is attenuated by sphingosine 1-phosphate signalling. J. Cell. Sci. 128(21), 3878-3887 (2015).

    2. Hawkins-Salsbury, J., Parameswar, A.R., Jiang, X., et al. Psychosine, the cytotoxic sphingolipid that accumulates in globoid cell leukodystrophy, alters membrane architecture. J. Lipid. Res. 54(12), 3303-3311 (2013).

    3. Hannun, Y.A., and Bell, R.M. Lysosphingolipids inhibit protein kinase C: Implications for the sphingolipidoses. Science 235(4789), 670-674 (1987).

    4. Haq, E., Contreras, M.A., Giri, S., et al. Dysfunction of peroxisomes in twitcher mice brain: A possible mechanism of psychosine-induced disease. Biochem. Biophys. Res. Commun. 343(1), 229-238 (2006).