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860580 | 02:0 SM (d18:1/2:0)

N-acetyl-D-erythro-sphingosylphosphorylcholine

02:0 SM (d18:1/2:0)

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5mg 860580P-5mg 860580P-5mg 1 x 5mg $534.25
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02:0 SM (d18:1/2:0)

N-acetyl-D-erythro-sphingosylphosphorylcholine

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. Sphingomyelin metabolism at the plasma membrane: implications for bioactive sphingolipids. FEBS Lett. 584, 1887-1894 (2010). [PubMed]
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C25H51N2O6P
Percent Composition
C 59.27%, H 10.15%, N 5.53%, O 18.95%, P 6.11%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
148306-05-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
506.656
Exact Mass
506.348
Synonyms
<p>Acetyl SphingomyelinN-(acetyl)-sphing-4-enine-1-phosphocholine</p>
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References

Bakrac B, Gutiérrez-Aguirre I, Podlesek Z, Sonnen AF, Gilbert RJ, Macek P, Lakey JH, Anderluh G. Molecular determinants of sphingomyelin specificity of a eukaryotic pore-forming toxin. J Biol Chem. 2008 Jul 4;283(27):18665-77. doi: 10.1074/jbc.M708747200. Epub 2008 Apr 28. PMID: 18442982.

 PubMed ID: 18442982
Certificates of Analysis

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