860587 | 18:1 SM (d18:1/18:1(9Z))

N-oleoyl-D-erythro-sphingosylphosphorylcholine


Chloroform

Size SKU Packaging Price
1mg 860587C-1mg 860587C-1mg 1 x 1mg 1mg/mL 1mL $250.00
5mg 860587C-5mg 860587C-5mg 1 x 5mg 5mg/mL 1mL $396.05

Powder

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5mg 860587P-5mg 860587P-5mg 1 x 5mg $396.05
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18:1 SM (d18:1/18:1(9Z))

18:1 SM (d18:1/18:1(9Z))

N-oleoyl-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
C41H81N2O6P
Percent Composition
C 67.54%, H 11.20%, N 3.84%, O 13.17%, P 4.25%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
108392-10-5
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
729.081
Exact Mass
728.583
Synonyms
<p>Oleoyl SphingomyelinN-(9Z-octadecenoyl)-sphing-4-enine-1-phosphocholine</p>

Nazemidashtarjandi S, Vahedi A, Farnoud AM. Lipid Chemical Structure Modulates the Disruptive Effects of Nanomaterials on Membrane Models. Langmuir. 2020 Apr 20. doi: 10.1021/acs.langmuir.0c00295. Epub ahead of print. PMID: 32312045.

PubMed ID: 32312045

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PubMed ID: 31363100

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PubMed ID: 31250362

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PubMed ID: 31141342

Holopainen M, Colas RA, Valkonen S, Tigistu-Sahle F, Hyvärinen K, Mazzacuva F, Lehenkari P, Käkelä R, Dalli J, Kerkelä E, Laitinen S. Polyunsaturated fatty acids modify the extracellular vesicle membranes and increase the production of proresolving lipid mediators of human mesenchymal stromal cells. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Jun 15;1864(10):1350-1362. doi: 10.1016/j.bbalip.2019.06.010. [Epub ahead of print]

PubMed ID: 31207356

Liu X, Bu J, Zhou X, Ouyang Z. Tandem Analysis by a Dual-Trap Miniature Mass Spectrometer. Anal Chem. 2018 Nov 28. doi: 10.1021/acs.analchem.8b03958. [Epub ahead of print].

PubMed ID: 30444599

Nyholm TKM, Jaikishan S, Engberg O, Hautala V, Slotte JP. The Affinity of Sterols for Different Phospholipid Classes and Its Impact on Lateral Segregation. Biophys J. 2019 Jan 22;116(2):296-307. doi: 10.1016/j.bpj.2018.11.3135. Epub 2018 Dec 6.

PubMed ID: 30583790