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16:0 SM (d18:1/16:0) | 860584

N-palmitoyl-D-erythro-sphingosylphosphorylcholine

860584P

Powder

860584P-
5mg
$352.00
860584P-
10mg
$630.00
860584P-
25mg
$1386.00

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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]
Molecular Formula
C39H79N2O6P
Percent Composition
C 66.63%, H 11.33%, N 3.98%, O 13.65%, P 4.41%
Purity
>99%
Stability
1 Years
Storage
-20°C
CAS Number
6254-89-3
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
703.028
Exact Mass
702.568
Transition Temp
40.5°C
Synonyms
Hexadecanoyl Sphingomyelin
N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine
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Notes
GIF Graphics File. 
GIF Graphics File. 
MDL Molfile. 
CDX File. 
Mark J. Richards and Susan Daniel, Two-Phase Contiguous Supported Lipid Bilayer Model for Membrane Rafts via Polymer Blotting and Stenciling, Langmuir, Article ASAP DOI: 10.1021/acs.langmuir.6b04385

Maria J. Sarmento, Ana Coutinho, Aleksander Fedorov, Manuel Prieto, and Fabio Fernandes. Membrane Order Is a Key Regulator of Divalent Cation-Induced Clustering of PI(3,5)P2 and PI(4,5)P2. Langmuir. Article ASAP. [PubMed]