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N-Hexadecanoyl-D-erythro-sphingosine (C16 sphingolipid base)

CATALOG # 2077


  • Catalog #:2077
  • Scientific Name:N-Hexadecanoyl-D-erythro-sphingosine (C16 sphingolipid base)
  • Common Name:N-Palmitoyl-D-erythro-sphingosine (C16 sphingolipid base)
  • Empirical Formula:C32H63NO3
  • CAS#:123065-37-2
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:510
  • Unit:1 mg
  • Source:synthetic
  • Purity:98%
  • Analytical Methods:TLC; HPLC; identity confirmed by MS
  • Solubility:chloroform, warm ethanol, warm methanol
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No


Application Notes:

N-Hexadecanoyl-D-erythro-C16-sphingosine is a well-defined ceramide and is ideal for use as a standard and in biological systems1. This product has the C16 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.2 Hexadecanoyl ceramide comprises a significant amount of natural ceramides, often being the second most abundant species after C18:0- ceramide. Ceramides function as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.3 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.4 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.5 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity.

1. M. Morrow et al. “Ceramide-1-phosphate, in contrast to ceramide, is not segregated into lateral lipid domains in phosphatidylcholine bilayers” Journal of Biophysics, Vol. 96(6) pp. 2216-2226, 2009
2. N. Zitomer et al. “A single extraction method for the analysis by liquid chromatography/tandem mass spectrometry of fumonisins and biomarkers of disrupted sphingolipid metabolism in tissues of maize seedlings” Analytical & Bioanalytical Chemistry, Vol. 391 pp. 2257-2263, 2008
3. J. M. Hauser, B. M. Buehrer, and R. M. Bell “Role of ceramide in mitogenesis induced by exogenous sphingoid bases.” Journal of Biological Chemistry Vol. 269 pp. 6803, 1994
4. N. S. Radin, “Killing tumours by ceramide-induced apoptosis: a critique of available drugs” Biochemical Journal, Vol. 371 pp. 243-256, 2003
5. N. S. Radin, “Designing anticancer drugs via the achilles heel: ceramide, allylic ketones, and mitochondria” Bioorganic and Medicinal Chemistry, Vol. 11(10) pp. 2123-2142, 2003
Price $435.00

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