A sphingolipid
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1-β-D-Glucosylsphingosine

Item No. 31556

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl, β-D-glucopyranoside
CAS Number
52050-17-6
Synonyms
  • GlcSph(d18:1)
  • Glucosyl-C18-sphingosine
  • Glucosylsphingosine (d18:1)
  • Lyso-Gb1
  • Lyso-GL1
Molecular Formula
C24H47NO7
Formula Weight
461.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): solubleEthanol: solubleMethanol: soluble
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-JIAPQYILSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    1-β-D-Glucosylsphingosine is a glucosylsphingosine, which are deacylated lysolipid derivatives of glucocerebrosides (Item Nos. 23206 | 23207 | 25850).1 They are formed when sphingosines undergo glucosidation by UDP-glucose.2 Glucosylsphingosines completely reduce neurite outgrowth and induce death of LA-N-2 cells when used at concentrations of 10 and 50 μM, respectively. They also decrease the activity of glucocerebrosidase in LA-N-2 cells in a concentration-dependent manner. Glucosylsphingosine levels are elevated in patients with Gaucher's disease, both in the spleen (in types 1, 2, and 3) and brain (types 2 and 3), thus, glucosylsphingosine has been used as a key biomarker of the disease.1,3 This product contains 1-β-D-glucosylsphingosine (d18:1) isolated from bovine buttermilk. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1306]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Murugesan, V., Chuang, W.-L., Liu, J., et al. Glucosylsphingosine is a key biomarker of Gaucher disease. Am. J. Hematol. 91(11), 1082-1089 (2016).

    2. Schueler, U.H., Kolter, T., Kaneski, C.R., et al. Toxicity of glucosylsphingosine (glucopsychosine) to cultured neuronal cells: A model system for assessing neuronal damage in Gaucher disease type 2 and 3. Neurobiol. Dis. 14(3), 595-601 (2003).

    3. Orvisky, E., Park, J.K., LaMarca, M.E., et al. Glucosylsphingosine accumulation in tissues from patients with Gaucher disease: Correlation with phenotype and genotype. Mol. Genet. Metab. 76(4), 262-270 (2002).