860592 | 24:0 SM

N-lignoceroyl-D-erythro-sphingosylphosphorylcholine

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24:0 SM

24:0 SM

N-lignoceroyl-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
Yes
Light Sensitive
No
Molecular Formula
C47H95N2O6P
Percent Composition
C 69.24%, H 11.75%, N 3.44%, O 11.78%, P 3.80%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
60037-60-7
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
815.241
Exact Mass
814.693
Synonyms
24:0 SM (d18:1/24:0)
C24 sphingomyelin
Lignoceroyl Sphingomyelin
N-(tetracosanoyl)-sphing-4-enine-1-phosphocholine

Ventura AE, Varela ARP, Dingjan T, Santos TCB, Fedorov A, Futerman AH, Prieto M, Silva LC. Lipid domain formation and membrane shaping by C24-ceramide. Biochim Biophys Acta Biomembr. 2020 Jun 18;1862(10):183400. doi: 10.1016/j.bbamem.2020.183400. Epub ahead of print. PMID: 32565121.

 PubMed ID: 32565121

Afşar E, Kırımlıoglu E, Çeker T, Yılmaz Ç, Demir N, Aslan M. Effect of ER stress on sphingolipid levels and apoptotic pathways in retinal pigment epithelial cells. Redox Biol. 2020 Feb;30:101430. doi: 10.1016/j.redox.2020.101430. Epub 2020 Jan 20. PMID: 31978676; PMCID: PMC6976939.

 PubMed ID: 31978676

Balleza D, Mescola A, Marín-Medina N, Ragazzini G, Pieruccini M, Facci P, Alessandrini A. Complex Phase Behavior of GUVs Containing Different Sphingomyelins. Biophys J. 2019 Feb 5;116(3):503-517. doi: 10.1016/j.bpj.2018.12.018. Epub 2019 Jan 3.

 PubMed ID: 30665697

Leurs CE, Lopes Pinheiro MA, Wierts L, den Hoedt S, Mulder MT, Eijlers AJC, Schoonheim MM, Balk LJ, Uitdehaag BMJ, Killestein J, de Vries HE. Acid sphingomyelinase: No potential as a biomarker for multiple sclerosis. Mult Scler Relat Disord. 2019 Feb;28:44-49. doi: 10.1016/j.msard.2018.11.024. Epub 2018 Nov 30.

 PubMed ID: 30553168

Acyl Chain Length and Saturation Modulate Interleaflet Coupling in Asymmetric Bilayers: Effects on Dynamics and Structural Order. Salvatore Chiantia and Erwin London, Biophysical Journal, Volume 103, Issue 11, 2311-2319, 5 December 2012.