N-Hexanoyl-glucosylceramide

This product is a well-defined glucosylceramide containing hexanoic acid making it ideal as an internal standard and for biological systems. Due to the short acyl-chain of the ceramide this product is more water soluble than natural cerebrosides and can therefore more easily cross cell membranes. Glucosylceramide is a major constituent of skin lipids where it has an important role in lamellar body formation and in maintaining the water permeability barrier. Glucocerebroside is very important due to its function as the biosynthetic precursor of lactosylceramide and from there of most of the neutral oligoglycolipids and gangliosides.1 Glucocerebroside is found in plants, fungi, and animals and is one of the most abundant glycosphingolipids in plants. Due to the relatively high melting point of cerebrosides (much greater than physiological body temperature) they have a para-crystalline structure. Glucocerebrosides tend to be concentrated in the outer leaflet of the plasma membrane in lipid rafts. It has been reported that glucocerebrosides are essential for the activity of tyrosinase (a key enzyme in melanin biosynthesis), to elicit defense responses in plants, and to help the plasma membrane in plants to withstand stresses brought about by cold and drought. In Gaucher disease glucocerebrosides accumulate in the spleen, liver, lungs, bone marrow, and brain due to a deficiency of the enzyme glucocerebrosidase.2,3 This accumulation of glucocerebroside has been associated with chemotherapy resistance. Glucocerebroside has been shown to be able to modulate membrane traffic along the endocytic pathway.4