b-D-Glucopyranosyl-1,1'-N-Docosanoyl-2'-Docosanamide-4'-octadecene-1',3'-diol Chemical Properties

Boiling point:

887.4±65.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Chloroform: Soluble

form 

A solid

pka

12.92±0.70(Predicted)

b-D-Glucopyranosyl-1,1'-N-Docosanoyl-2'-Docosanamide-4'-octadecene-1',3'-diol Usage And Synthesis

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 , 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.

Definition

ChEBI: Beta-D-glucosyl-N-(docosanoyl)sphingosine is a beta-D-glucosylceramide where the ceramide N-acyl group is specified as docosanoyl. It has a role as a mouse metabolite. It is functionally related to a docosanoic acid.

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-Nú?ez, 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).