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Sphingomyelin

As a major constituent of cell membranes, sphingomyelin is found at particularly high concentrations in the membranes of nerve cells (in the myelin sheaths) and red blood cells. It was previously thought to have a purely structural role, similar to the function of phosphatidylcholine, through intermolecular interactions mediated by the 2-amide group, the 3-hydroxy group and the 4,5-trans double bond of the sphingoid base1. However, it is now appreciated that sphingomyelin has a high affinity for cholesterol and that these two lipids pack tightly into liquid-ordered domains among a liquid-disordered phase to form lipid rafts1,2. These membrane microdomains are thought to function as signaling platforms that regulate the localization and interactions of proteins. But sphingomyelin does not just influence signaling as a component of lipid rafts — it is also a precursor to ceramides and other sphingolipid metabolites that comprise the sphingomyelin cycle or sphingolipid network1,2.
1. Christie, W.W. Sphingomyelin and related lipids. The AOCS Lipid Library.
2. Milhas, D., Clarke, C.J. & Hannun, Y.A. (2010) Sphingomyelin metabolism at the plasma membrane: implications for bioactive sphingolipids. FEBS Lett. 584:1887-1894. [PubMed]
Additional References:

Slotte, J.P. (2013) Biological functions of sphingomyelins. Prog Lipid Res 52:424-437. [PubMed]

Quinn, P.J. (2013). Structure of Sphingomyelin Bilayers and Complexes with Cholesterol Forming Membrane Rafts.  Langmuir [PubMed]


Natural

Brain SM
Egg SM
Milk SM

Synthetic SM & Derivatives

02:0 SM (d18:1/2:0)
06:0 SM (d18:1/6:0)
12:0 SM (d18:1/12:0)
12:0 Dihydro SM (d18:0/12:0)
16:0 SM (d18:1/16:0)
17:0 SM (d18:1/17:0)
18:0 SM (d18:1/18:0)
18:1 SM (d18:1/18:1(9Z))
24:0 SM
24:1 SM
Lyso SM (d18:1)
Lyso SM (d17:1)
Lyso SM (dihydro) (d18:0)