860593 | 24:1 SM

N-nervonoyl-D-erythro-sphingosylphosphorylcholine


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24:1 SM

24:1 SM

N-nervonoyl-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
C47H93N2O6P
Percent Composition
C 69.42%, H 11.53%, N 3.44%, O 11.80%, P 3.81%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
94359-13-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
813.225
Exact Mass
812.677
Synonyms
24:1 SM (d18:1/24:1(15Z))
C24:1 sphingomyelin
Nervonoyl Sphingomyelin
N-(15Z-tetracosenoyl)-sphing-4-enine-1-phosphocholine

Govindarajan S, Verheugen E, Venken K, Gaublomme D, Maelegheer M, Cloots E, Gysens F, De Geest BG, Cheng TY, Moody DB, Janssens S, Drennan M, Elewaut D. ER stress in antigen-presenting cells promotes NKT cell activation through endogenous neutral lipids. EMBO Rep. 2020 Jun 4;21(6):e48927. doi: 10.15252/embr.201948927. Epub 2020 May 3. PMID: 32363653; PMCID: PMC7271650.

PubMed ID: 32363653

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

Sjödin MOD, Checa A, Yang M, Dahlén SE, Wheelock ÅM, Eklund A, Grunewald J, Wheelock CE. Soluble epoxide hydrolase derived lipid mediators are elevated in bronchoalveolar lavage fluid from patients with sarcoidosis: a cross-sectional study. Respir Res. 2018 Dec 3;19(1):236. doi: 10.1186/s12931-018-0939-0.

PubMed ID: 30509266

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

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