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D-erythro-C12-Sphingosine

CATALOG # 1838

Specifications

  • Catalog #:1838
  • Scientific Name:D-erythro-C12-Sphingosine
  • Common Name:Sphingosine with C12 chain
  • Empirical Formula:C12H25NO2
  • CAS#128427-86-1
  • SDSView Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:215
  • Unit:5 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, HPLC, identity confirmed by MS
  • Solubility:chloroform, methanol, ethanol, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No

Description

Application Notes:

Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others.1 It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18-carbon chain and a double bond at carbon 4 is the most abundant sphingosine in animal tissues. D-erythro-C12-sphingosine is a shortchain analog of natural sphingosine that exhibits different cellular effects from the long-chain sphingosines. This shorter long chain base is considerably less hydrophobic which could significantly change the process of signal transduction.2 Lysosphingolipids (such as sphingosine) inhibit protein kinase C activity resulting in the pathogenesis of sphingolipidoses such as Krabbe's disease and Gaucher's disease but short-chain C12-sphingosine does not demonstrate this inhibitory action.3 Sphingosine can be phosphorylated via two kinases to form sphingosine-1-phosphate, which has important signaling functions. While sphingosines and ceramides can induce apoptosis,4 sphingosine-1-phosphate can promote cell survival or proliferation. Sphingosine has been shown to cause an increase in the cytoplasmic calcium level of cells.

References:
1. A. Merrill, Jr. “De Novo Sphingolipid Biosynthesis: A Necessary, but Dangerous, Pathway” The Journal of Biological Chemistry, Vol. 277(29) pp. 25843–25846, 2002
2. H. Fyrst et al. “Characterization of free endogenous C14 and C16 sphingoid bases from Drosophila melanogaster” Journal of Lipid Research, Vol. 45 pp. 54-62, 2004
3. K. Sandhoff et al. “Sphingolipid biosynthesis in cultured neurons” European Journal of Biochemistry, vol. 198 pp. 667-674, 1991
4. V. Nava et al. “Sphingosine Enhances Apoptosis of Radiation-resistant Prostate Cancer Cells” Cancer Research, Vol. 60 pp. 4468-4474, 2000
Price $325.00

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