N-Hexanoyl-D-threo-sphingosine

CATALOG # 1809
Amount 1 mg
Price $190.00
Qty
 
C24H47NO3
  • Catalog #:1809
  • Scientific Name:N-Hexanoyl-D-threo-sphingosine
  • Common Name:N-C6:0-D-threo-Ceramide
  • Empirical Formula:C24H47NO3
  • CAS#189894-79-9
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:398
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC; identity confirmed by MS
  • Solubility:chloroform, methanol, DMSO (up to 5 mg/ml)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    Ceramide is a fatty acid amide of sphingosine. This product is a well-defined ceramide with a hexanoyl acyl group. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1- phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein).4 It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. Ceramides with short side chains have been shown to enter easily into cells where they are biologically active. Ceramides with longer side chains also enter cells if dissolved in dodecane-isopropanol first.

    References:
    1. J. Hauser, B. Buehrer, and R. Bell, Journal of Biological Chemistry Vol. 269 pp. 6803, 1994
    2. N. Radin, Biochemical Journal, Vol. 371 pp. 243-256, 2003
    3. N. Radin, Bioorganic and Medicinal Chemistry, Vol. 11(10) pp. 2123-2142, 2003
    4. M. Yano, E. Kishida, Y. Muneyuki, and Y. Masuzawa, Journal of Lipid Research, Vol. 39 pp. 2091-2098, 1998