A sphingolipid
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Glucosylceramide (plant)

Item No. 25850

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
497155-61-0
Synonyms
  • GluCer (soy)
Molecular Formula
C40H75NO9 (for 2-hydroxy hexadecanoyl)
Formula Weight
714.0
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol (2:1): SolubleChloroform:Methanol (2:1): soluble
SMILES
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CC/C=C/CCCCCCCCC)NC([R])=O)[C@@H]1O
InChi Code
InChI=1S/C40H75NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,26,28,32-38,40,42-47H,3-18,21-25,27,29-31H2,1-2H3,(H,41,48)/b20-19+,28-26+/t32-,33+,34?,35+,36+,37-,38+,40+/m0/s1
InChi Key
HOMYIYLRRDTKAA-BEYQCJBTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $123

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    10 mg

    $195

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    50 mg

    $902

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    100 mg

    $1,669

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    Product Description

    Glucosylceramides are formed by the tethering of glucose to a ceramide by glucosylceramide synthase.1 They are present in neuronal and non-neuronal mammalian tissues and are found at low quantities in a large number of plant species, where they comprise 5-30% of total lipids in the plant plasma membrane, and in fungi.1,2,3 Glucosylceramides levels decrease during cold acclimatization in plants and glucosylceramides in fungi are involved in the regulation of virulence and act as elicitors in plants, stimulating plant defense mechanisms.3,4 Glucosylceramides are precursors in the synthesis of lactosylceramides and gangliosides. Increased levels of glucosylceramides are associated with obesity-induced insulin resistance in mice and with neuronal deficits observed in neuronopathic Gaucher disease.1,5 This product contains glucosylceramide molecular species with primarily 2-hydroxy C16:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1522]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Holland, W.L., and Summers, S.A. Sphingolipids, insulin resistance, and metabolic disease: New insights from in vivo manipulation of sphingolipid metabolism. Endocr. Rev. 29(4), 381-402 (2008).

    2. Cahoon, E.B., and Lynch, D.V. Analysis of glucocerebrosides of rye (Secale cereale L. cv Puma) leaf and plasma membrane. Plant Physiol. 95(1), 56-68 (1991).

    3. Lynch, D.V., and Dunn, T.M. An introduction to plant sphingolipids and a review of recent advances in understanding their metabolism and function. New Phytol. 161(3), 667-702 (2004).

    4. Rollin-Pinheiro, R., Bernardino, M.C., and Barreto-Bergter, E. Sphingolipids: Functional and biological aspects in mammals, plants, and fungi. Analysis of membrane lipids 21-40 (2020).

    5. Dai, M., Liou, B., Swope, B., et al. Progression of behavioral and CNS deficits in a viable murine model of chronic neuronopathic Gaucher disease. PLoS One 11(9), e0162367 (2016).