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CATALOG # 2043


  • Catalog #:2043
  • Scientific Name:N-(R,S)-alpha-Hydroxydodecanoyl-D-erythro-dihydrosphingosine
  • Common Name:N-(R,S)-alpha-Hydroxy-C12:0-D-erythro-dihydroceramide
  • Empirical Formula:C30H61NO4
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:500
  • Unit:5 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:GC, TLC, identity confirmed by MS
  • Solubility:chloroform/methanol/water, 2:1:0.5
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No


Application Notes:

This product is a high purity alpha-hydroxydihydroceramide and is ideal as a standard and for biological studies. 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 sphinganine and sphinganine-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 or into phytosphingosine via the C4-hydrozylase enzyme.1 The presence of a hydroxyl group on the fatty acyl chain of dihydroceramides significantly affects the function and properties of the molecule. While 2(S)-hydroxydihydroceramides can be converted to non-hydroxydihydroceramides in vivo 2(R)-hydroxydihydroceramides cannot. Data presented suggests that 2(R)-hydroxydihydroceramides may interact with some distinct cellular regulatory targets in a specific and more effective manner than their nonhydroxylated analogs.2 2-hydroxydihydroceramides have been shown to be incorporated into the galactosylceramides and sulfatides of the myelin where they are essential to neuronal functions.3

1. 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
2. Z. Szulc et al. “Synthesis, NMR characterization and divergent biological actions of 2-hydroxy-ceramide/dihydroceramide stereoisomers in MCF7 cells” Bioorg Med Chem, vol. 18 pp. 7565-7579, 2010
3. M. Kruer et al. “Defective FA2H leads to a novel form of neurodegeneration with brain iron accumulation (NBIA)” Annals of Neurology, vol. 68 pp. 611- 618, 2010
Price $310.00

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