N-Hexanoyl-NBD-D-erythro-dihydrosphingosine

CATALOG # 1626
Amount 100ug
Price $200.00
Qty
 
N-Hexanoyl-NBD-D-erythro-dihydrosphingosine
  • Catalog #:1626
  • Scientific Name:N-Hexanoyl-NBD-D-erythro-dihydrosphingosine
  • Common Name:N-C6:0-NBD-Dihydroceramide; N-C6:0-NBD-D-erythro-Dihydrosphingosine
  • Empirical Formula:C30H51N5O6
  • CAS#114301-95-0
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:578
  • Unit:100ug
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC; identity confirmed by MS
  • Natural Source:n/a
  • Melting Point:n/a
  • Solubility:chloroform/methanol,2:1; methanol
  • Physical Appearance:solid
  • Storage:-20°C
  • Composition:n/a
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This high purity fluorescent product is ideal for the identification of dihydroceramide in samples and biological systems. 7- nitrobenzofurazan (NBD) has been shown to have only a small influence on lipid adsorption into cells and cellular membranes. This fluorescent analog of natural dihydroceramide is comparable to C6:0-dyhidroceramide in many biological functions.1,2 Dihydroceramide is a critical intermediate in the synthesis of many complex sphingoid bases. Inhibition of dihydroceramide synthesis by some fungal toxins that have a similar structure causes an increase in dihydroceramide and dihydroceramide-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer. Dihydroceramide, synthesized by the acylation of sphinganine, is subsequently converted into ceramide via a desaturase enzyme. N-(4-Hydroxyphenyl) retinamide (4-HPR) has been tested as an anti-cancer agent. It inhibits the dihydroceramide desaturase enzyme in cells resulting in a high concentration of dihydroceramide and dihydro-sphingolipids and this is thought to be the cause of the anti-cancer effects.3 Dihydrosphingosine induces cell death in a number of types of malignant cells.

    References:
    1. G van Meer et al. “Epithelial sphingolipid sorting allows for extensive variation of the fatty acyl chain and the sphingosine backbone” Journal of Biochemistry, vol. 283 pp. 913-917, 1992
    2. A. Merrill, Jr. et al. “Dihydroceramide Biology STRUCTURE-SPECIFIC METABOLISM AND INTRACELLULAR LOCALIZATION” Journal of Biological Chemistry, vol. 272 pp. 21128-21136, 1997
    3. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006