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Sphingosine with C12 chain

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.
Cat# Size Price Qty Buy
1838 5 mg £290.70

Additional Information

Property Value or Rating
Product Size 5 mg
Manufacturer Matreya, LLC
Empirical Formula C12H25NO2
CAS# 128427-86-1
Formula Weight 215.3
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC, identity confirmed by MS
Natural Source Synthetic
Solubility chloroform, methanol, ethanol
Physical Appearance A neat solid
Storage -20°C

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

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