N-omega-CD3-Octadecanoyl-D-erythro-dihydrosphingosine

CATALOG # 2202
Amount 1 mg
Price $275.00
Qty
 
N-omega-CD3-Octadecanoyl-D-erythro-dihydrosphingosine
  • Catalog #:2202
  • Scientific Name:N-omega-CD3-Octadecanoyl-D-erythro-dihydrosphingosine
  • Common Name:N-C18:0-CD3-D-erythro-Dihydroceramide; N-Stearoyl-CD3-D-erythro-sphinganine
  • Empirical Formula:C36H70D3NO3
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:571
  • Unit:1 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC, HPLC, identity confirmed by MS
  • Solubility:hot ethanol, DMF, DMSO, chloroform/methanol 2:1
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No
  • Literature References:Application Notes:

    This product is a well-defined dihydroceramide containing a deuterated stearic acid acylated to a sphinganine base making it an ideal stable isotope-labeled standard for lipidomic studies using mass spectrometry. Stable isotope-labeled tracers are ideal for studies involving the metabolism and various metabolites of a lipid and can be used for the quantitative evaluation of major lipid pathways.1 Lipidomics has shown great success in the use of deuterium labeled compounds in identifying and quantifying individual molecular species by the use of tandem mass spectrometry.2 Dihydroceramide is a critical intermediate in the de novo synthesis of ceramide, leading to many complex sphingolipids. It is synthesized by the acylation of sphinganine (dihydrosphingosine) and is subsequently converted to ceramide via the enzyme dihydroceramide desaturase or into phytosphingosine via the enzyme C4-hydroxylase.3 Inhibition of ceramide synthase by some fungal toxins (such as fumonisin B1) causes an accumulation of sphinganine and sphinganine-1- phosphate and a decrease in dihydroceramide and other dihydrosphingolipids, leading to a number of diseases including oesophageal cancer.4 The dihydroceramide desaturase inhibitor N-(4-Hydroxyphenyl) retinamide (4-HPR) has been tested as an anti-cancer agent by inhibiting 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 its anti-cancer effects.5 Oxidative stress in cells causes an increase in the amount of dihydroceramide by potently inhibiting the desaturase enzyme.6 Dihydroceramide inhibits the formation of channels by ceramides and may thus reduce ceramide induced apoptosis in cells.7

    References:
    1. Magkos, F. and Mittendorfer, B., “Stable isotope-labeled tracers for the investigation of fatty acid and triglyceride metabolism in humans in vivo” Clin Lipidol. Vol. 4 pp. 215–230, 2009
    2. Byun, H. and Bittman, R. Selective deuterium labeling of the sphingoid backbone: facile syntheses of 3,4, 5-trideuterio-d-erythro-sphingosine and 3- deuterio-d-erythro-sphingomyelin” Chem Phys Lipids, Vol. 163(8) pp. 809-813, 2010
    3. Y. Mizutani, A. Kihara, and Y. Igarashi “Identifcation of the human sphingolipid C4-hydroxylase, hDES2, and its up-regulation during keratinocyte differentiation” FEBS Letters, vol. 563 pp. 93-97, 2004
    4. J. Soriano et al. “Mechanism of action of sphingolipids and their metabolites in the toxicity of fumonisin B1” Progress in Lipid Research, Vol. 44 pp. 345-356, 2005
    5. W. Zheng “Fenretinide increases dihydroceramide and dihydrosphingolipids due to inhibition of dihydroceramide desaturase” Georgia Institute of Technology, 2006
    6. J. Idkowiak-Baldys et al. “Dihydroceramide Desaturase Activity is Modulated by Oxidative Stress” Biochem. J., Vol. 427(2) pp. 265-274, 2010
    7. J. Stiban et al. “Dihydroceramide hinders ceramide channel formation: Implications on apoptosis” Apoptosis, Vol. 11(5) pp. 773-780, 2006