N-Octanoyl-L-threo-sphingosine

CATALOG # 1830
Amount 1 mg
Price $190.00
Qty
 
C26H51NO3
  • Catalog #:1830
  • Scientific Name:N-Octanoyl-L-threo-sphingosine
  • Common Name:N-C8:0-L-threo-Ceramide
  • Empirical Formula:C26H51NO3
  • CAS#175892-44-1
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:426
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC
  • Solubility:chloroform, ethanol, DMSO,DMF (up to 5 mg/ml)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is a high purity, non-natural L-threo ceramide that is ideal as a standard and for biological studies. D-erythro Ceramide is the natural ceramide isomer and is involved in many biological processes including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.1 Both the natural D-erythro and the non-natural L-erythro and the D- and L-threo ceramides display similar effectiveness in inducing apoptotic damage in cells.2 The protein phosphatases PP1 and PP2A, which are involved in regulating apoptosis and cell growth, are activated by D-erythro ceramide but inhibited by L-threo, D-threo, and L-erythro ceramide.3 Both D-erythro and D-threo C2 ceramides have been found to be potent inducers of IL-6 production, while neither the L-threo or L-erythro stereoisomers of ceramide were effective.4 D- and L-erythro ceramide and D- and L-threo ceramide are also comparably effective inhibitors of protein kinase C.5

    References:
    1. 2. N. S. Radin, “Killing tumours by ceramide-induced apoptosis: a critique of available drugs” Biochemical Journal, Vol. 371 pp. 243-256, 2003
    2. W. Jarvis et al. “Induction of Apoptosis and Potentiation of Ceramide-mediated Cytotoxicity by Sphingoid Bases in Human Myeloid Leukemia Cells” The Journal of Biological Chemistry, Vol. 271 pp. 8275-8284, 1996
    3. C. Chalfant et al. “Long Chain Ceramides Activate Protein Phosphatase-1 and Protein Phosphatase-2A Activation is Stereospecific and Regulated by Phosphatidic Acid” The Journal of Biological Chemistry, Vol. 274 pp. 20313-20317, 1999
    4. S. Laulederkind et al. “Ceramide Induces Interleukin 6 Gene Expression in Human Fibroblasts” The Journal of Experimental Medicine, Vol. 182 pp. 599-604, 1995
    5. T. Ariga et al. “Role of sphingolipid-mediated cell death in neurodegenerative diseases” Journal of Lipid Research, Vol. 39 pp. 1-16, 1998