N-Hexanoyl-L-erythro-sphingosine

CATALOG # 1848
Amount 1 mg
Price $170.00
Qty
 
C24H47NO3
  • Catalog #:1848
  • Scientific Name:N-Hexanoyl-L-erythro-sphingosine
  • Common Name:N-C6:0-L-erythro-Ceramide
  • Empirical Formula:C24H47NO3
  • 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, ethanol, DMSO, DMF (up to 5mg/ml)
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is the L-erythro stereoisomer of natural D-erythro-hexanoyl ceramide. L-erythro ceramides are inactive in some ceramide functions, have different activities in other functions, and exhibit the same activity in yet other functions. Lerythro- N-acetyl ceramide has been shown to induce accumulation of greater levels of sphingosine than in control cells.1 Generation of endogenous long-chain ceramide can be induced by exogenous short chain D-erythro-hexanoyl-ceramide but not by non-natural L-erythro-hexanoyl-ceramide.2 Other examples of functions demonstrated by D-erythro, but not Lerythro, ceramides are several key downstream biological activities such as growth inhibition, cell cycle arrest, and modulation of telomerase activity.2 Some viruses require the presence of ceramide in a membrane to be able to fuse to that membrane and it has been demonstrated that only D-erythro ceramide, and not L-erythro or D- or L-threo ceramides, supports the viral fusion.3

    References:
    1. Y. Lee et al. “Sphingolipid metabolic changes during chiral C2-ceramides induced apoptosis in human leukemia cells” Arch Pharm Res, vol. 24 pp. 144- 149, 2001
    2. Y. Hannun et al. “Biochemical Mechanisms of the Generation of Endogenous Long Chain Ceramide in Response to Exogenous Short Chain Ceramide in the A549 Human Lung Adenocarcinoma Cell Line” The Journal of Biological Chemistry, vol. 277 pp. 12960–12969, 2002
    3. J. Wilschut et al. “Sphingolipids Activate Membrane Fusion of Semliki Forest Virus in a Stereospecific Manner” Biochemistry, vol. 34 pp. 10319-10324, 1995