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N-C18:0-Sphingomyelin; N-Stearoyl-sphingosylphosphorylcholine

Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis. An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease and neonatal respiratory distress syndrome.1 However, the ratio of sphingomyelin to ceramide is different for different cell types.2 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.3 In contrast to ceramides, N-hexanoyl-sphingosylphosphorylcholine does not initiate vesicle formation in cells.4 N-hexanoyl-sphingosylphosphorylcholine has been used to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.5
Cat# Size Price Qty Buy
1911 5 mg £223.55

Additional Information

Property Value or Rating
Product Size 5 mg
Manufacturer Matreya, LLC
Empirical Formula C41H83N2O6P
CAS# 58909-84-5
Formula Weight 731.1
Solvent none
Source semisynthetic
Purity 98+%
Analytical Methods TLC
Natural Source Semi-synthetic|Animal/Bovine buttermilk
Solubility chloroform, ethanol, methanol
Physical Appearance A neat solid
Storage -20°C

1. C. St Clair et al. “The probability of neonatal respiratory distress syndrome as a function of gestational age and lecithin/sphingomyelin ratio” Am J Perinatol., Vol. 25(8) pp. 473-480, 2008, 
2. J. Kilkus et al. “Differential regulation of sphingomyelin synthesis and catabolism in oligodendrocytes and neurons” J Neurochem. Vol. 106(4) pp. 1745- 1757, 2008 
3. N. Duan RD. “Absorption and lipoprotein transport of sphingomyelin” J Lipid Res., Vol. 47(1) pp. 154-171, 2006 
4. R. Li, E. Blanchette-Mackie, and S. Ladisch “Induction of Endocytic Vesicles by Exogenous C6-ceramide” Journal of Biological Chemistry, vol. 274 pp. 21121-21127, 1999 
5. R. Veldman et al. “N-hexanoyl-sphingomyelin potentiates in vitro doxorubicin cytotoxicity by enhancing its cellular influx” Nature, vol. 90 pp. 917-925, 2004

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