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Sphingosine with C14 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 but D-erythro-C14-sphingosine is the most common long chain base (LCB) in some organisms such as Drosophila. This shorter LCB is considerably less hydrophobic which could significantly change the process of signal transduction.2 D-erythro-C14-sphingosine has recently been found to act as a germination-accelerating factor in silkworms with much greater activity than its shorter or longer homologues.3 Lysosphingolipids inhibit protein kinase C activity resulting in the pathogenesis of sphingolipidoses such as Krabbe's disease and Gaucher's disease. 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
1833 5 mg £290.70

Additional Information

Property Value or Rating
Product Size 5 mg
Manufacturer Matreya, LLC
Empirical Formula C14H29NO2
CAS# 24558-60-9
Formula Weight 243.4
Solvent none
Source synthetic
Purity 98+%
Analytical Methods TLC, GC, HPLC, identity confirmed by MS
Natural Source Synthetic
Solubility chloroform, methanol, ethanol, DMSO
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. T. Noda et al. “Characterization of a germination-accelerating factor from the silkworm (Bombyx mori Linnaeus) of entomopathogenic fungus Nomuraea rileyi (Farlow) Samson” Biosci Biotechnol Biochem, Vol. 74(6) pp. 1226-1230, 2010 
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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