N-Heptadecanoyl-lactosylceramide

CATALOG # 1538
Amount 1 mg
Price $235.00
Qty
 
N-Heptadecanoyl-lactosylceramide
  • Catalog #:1538
  • Scientific Name:N-Heptadecanoyl-lactosylceramide
  • Common Name:N-C17:0-Lactosylceramide; Lactosylceramide with C17:0 fatty acid side chain
  • Empirical Formula:C47H89NO13
  • CAS#1354699-26-5
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:876
  • Unit:1 mg
  • Source:semisynthetic
  • Purity:98+%
  • Analytical Methods:TLC, identity confirmed by MS
  • Natural Source:bovine, buttermilk
  • Solubility:chloroform/methanol/water, 2:1:0.1
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is a well-defined lactosylceramide containing a heptadecanoyl group acylated to the amine of the sphingosine and is ideal as an internal standard. Lactosylceramide is the precursor of many other glycosphingolipids and also functions as a second messenger and protein receptor, making it a very important organic molecule. Many cellular processes are dependent on lactosylceramide since it is the substrate for neutral oligoglycosylceramides, sulfatides and gangliosides, all of which have their own vital functions. Lactosylceramide also helps to stabilize the lipid membrane, activate receptor molecules and acts as a receptor for certain bacteria and toxins. In animals, where it is found mostly in epithelial and neuronal cells, it is expressed on neutrophils and macrophages where it binds to toxins and bacteria, which are then engulfed and eliminated. Its role as a second messenger has been found to be vital and dysfunctions in its processes can lead to cancer and inflammation since it is critical to neutrophil activity and in activating anti-inflammatory responses.1 Therefore, it is being studied for its use in cancer therapies and as a therapy for other diseases. Other examples of lactosylceramide second messenger functions are tumor necrosis factor  and platelet-derived growth factor. A deficiency in the enzyme responsible for hydrolyzing the galactose of lactosylceramide leads to lactosylceramidosis, which is characterized by an accumulation of lactosylceramide that causes a primary neurological disorder.2 Lactosylceramide is also important in the activation of platelet/endothelial cell adhesion molecule-1 which causes adhesion and diapedesis of monocytes/lymphocytes.3

    References:
    1. Ravinder Pannu et al. “A Novel Role of Lactosylceramide in the Regulation of Tumor Necrosis Factor alpha-mediated Proliferation of Rat Primary Astrocytes: IMPLICATIONS FOR ASTROGLIOSIS FOLLOWING NEUROTRAUMA” Journal of Biological Chemistry, Vol. 280 pp. 13742-13751, 2005
    2. Glyn Dawson “Glycosphingolipid levels in an unusual neurovisceral storage disease characterized by lactosylceramide galactosyl hydrolase deficiency: lactosylceramidosis” Journal of Lipid Research, Vol. 13 pp. 207-219, 1972
    3. NanLing Gong “Lactosylceramide recruits PKC and phospholipase A2 to stimulate PECAM-1 expression in human monocytes and adhesion to endothelial cells” Proceedings of the National Academy of Sciences, Vol. 101:17 pp. 6490-6495, 2004