An endogenous glucosylceramide
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C22 Glucosylceramide (d18:1/22:0)

Item No. 23210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,2R,3E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxy-3-heptadecen-1-yl]-docosanamide
CAS Number
119242-44-3
Synonyms
  • N-C22:0-Glucocerebroside
  • C22 Glucosylceramide
  • GlcCer(18:1/22:0)
  • GluCer(18:1/22:0)
  • Glucosylceramide (d18:1/22:0
  • N-Docosanoyl-β-glucosylsphingosine
  • N-Docosanoyl-glucopsychosine
Molecular Formula
C46H89NO8
Formula Weight
784.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble
SMILES
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O
InChi Code
InChI=1S/C46H89NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-42(50)47-39(38-54-46-45(53)44(52)43(51)41(37-48)55-46)40(49)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h33,35,39-41,43-46,48-49,51-53H,3-32,34,36-38H2,1-2H3,(H,47,50)/b35-33+/t39-,40+,41+,43+,44-,45+,46+/m0/s1
InChi Key
YIGARKIIFOHVPF-CNUVFPMCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $569

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    Product Description

    C22 Glucosylceramide is an endogenous glucosylceramide.1,2,3 Glucosylceramides are major constituents of skin lipid membranes where they play a role in maintaining the water permeability barrier. They are precursors in the synthesis of lactosylceramide (Item No. 16983), as well as oligoglycolipids and gangliosides. Phospholipase A2 (PLA2) type XIIA knockdown increases C22 glucosylceramide expression in rat brain.3 It is also increased in the brain, but not the liver or spinal cord, of mice fed a methionine-restricted diet.2 In human athletes, plasma levels of C22 glucosylceramide increase during exercise and return to basal levels during recovery.1 This product contains C22 glucosylceramide 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. 1531]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bergman, B.C., Brozinick, J.T., Strauss, A., et al. Serum sphingolipids: Relationships to insulin sensitivity and changes with exercise in humans. Am. J. Physiol. Endocrinol. Metab. 309(4), E398-E408 (2015).

    2. Jové, M., Ayala, V., Ramírez-Núñez, O., et al. Specific lipidome signatures in central nervous system from methionine-restricted mice. J. Proteome Res. 12(6), 2679-2689 (2013).

    3. Ee, S.-M., Lo, Y.-L., Shui, G., et al. Distribution of secretory phospholipase A2 XIIA in the brain and its role in lipid metabolism and cognition. Mol. Neurobiol. 50(1), 60-75 (2014).