N-Acetyl-D-erythro-sphingosine (C14 sphingolipid base)

CATALOG # 1842
Amount 5 mg
Price $285.00
Qty
 
C16H31NO3
  • Catalog #:1842
  • Scientific Name:N-Acetyl-D-erythro-C14 sphingolipid base
  • Common Name:N-C2:0-Ceramide of D-erythro-C14-sphingosine
  • Empirical Formula:C16H31NO3
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:285
  • Unit:5 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC, identity confirmed by MS
  • 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:

    N-Acetyl-D-erythro-C14-sphingosine is a well-defined ceramide and is ideal for use as a standard and in biological studies. This product has the C14 sphingoid base, which is less prevalent than the C18 base in most plants and animals making it very useful in determining sphingosine metabolism and derivatives and as an internal standard. Natural long-chain ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. It also exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.1 N-Acetyl-D-erythro-C16-sphingosine enters easily into cells where it is biologically active and has been shown to induce downregulation of Bcl-2 protein, inhibiting cell proliferation and inducing apoptosis.2 N-Acetylsphingosine demonstrates many of the biological activities associated with ceramides that contain long-chain fatty acids. However, it has also been found that N-acetyl-sphingosine may inhibit neutrophil superoxide release,3 stimulation of DNA synthesis, and phospholipase D activity. N-acetyl-sphingosine is different from sphingosine as seen by its inability to inhibit protein kinase C or cause calcium release.

    References:
    1. N. S. Radin, “Killing tumours by ceramide-induced apoptosis: a critique of available drugs” Biochemical Journal, Vol. 371 pp. 243-256, 2003
    2. N. Di Nardo et al. “Ceramide 2 (N-acetyl sphingosine) is associated with reduction in Bcl-2 protein levels by Western blotting and with apoptosis in cultured human keratinocytes” British Journal of Dermatology, Vol. 143 pp. 491-497, 2000
    3. K. Wong, X. Li, N. Hunchuk “N-Acetylsphingosine (C -ceramide) Inhibited Neutrophil Superoxide Formation and Calcium Influx” Journal of Biological Chemistry, Vol. 270 pp. 3056-3052, 1995