860585 | 17:0 SM (d18:1/17:0)

N-heptadecanoyl-D-erythro-sphingosylphosphorylcholine


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17:0 SM (d18:1/17:0)

17:0 SM (d18:1/17:0)

N-heptadecanoyl-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]
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C40H81N2O6P
Percent Composition
C 67.00%, H 11.39%, N 3.91%, O 13.39%, P 4.32%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
121999-64-2
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
717.055
Exact Mass
716.583
Synonyms
<p>Heptadecanoyl SphingomyelinN-(heptadecanoyl)-sphing-4-enine-1-phosphocholine</p>

Mi J, Han Y, Xu Y, Kou J, Li WJ, Wang JR, Jiang ZH. Deep Profiling of Immunosuppressive Glycosphingolipids and Sphingomyelins in Wild Cordyceps. J Agric Food Chem. 2018 Aug 20. doi: 10.1021/acs.jafc.8b02706. [Epub ahead of print]

PubMed ID: 30059214

Li G, Kim J, Huang Z, St Clair JR, Brown DA, London E. Efficient replacement of plasma membrane outer leaflet phospholipids and sphingolipids in cells with exogenous lipids. Proc Natl Acad Sci U S A. 2016 Dec 6;113(49):14025-14030. Epub 2016 Nov 21.

PubMed ID: 27872310