860592P
Avanti
24:0 SM
Avanti Polar Lipids 860592P, powder
Synonym(s):
N-lignoceroyl-D-erythro-sphingosylphosphorylcholine
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About This Item
Empirical Formula (Hill Notation):
C47H95N2O6P
CAS Number:
Molecular Weight:
815.24
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
form
powder
packaging
pkg of 1 × 10 mg (860592P-10mg)
pkg of 1 × 5 mg (860592P-5mg)
manufacturer/tradename
Avanti Polar Lipids 860592P
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O
General description
d-erythro (2S, 3R) sphingomyelin (C24:0-SM) is a synthetic sphingomyelin with acyl chain comprising 24 carbon atom. It is produced by the acylation of D-erythro-sphingosylphosphorylcholine. Sphingomyelin is a key constituent of mammalian cell plasma membranes. It is mainly found at high concentrations in the myelin sheaths of nerve cells, in brain, eye lens and red blood cells. SM have asymmetric molecular structure and high hydrogen-bonding capacity.
Application
24:0 sphingomyelin (SM) is suitable to study its thermotropic and mechanical properties by using differential scanning calorimetry. It is also suitable for use as a lipid standard in ultrafast liquid chromatography−tandem mass spectrometry.
Biochem/physiol Actions
Sphingomyelin (SM) are involved in the formation of functional domains in the membrane bilayer. It also acts as a precursor for sphingolipid signaling molecules including, ceramides and other sphingolipid metabolites.
Packaging
5 mL Amber Glass Screw Cap Vial (860592P-10mg)
5 mL Amber Glass Screw Cap Vial (860592P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
also commonly purchased with this product
Storage Class Code
11 - Combustible Solids
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Find documentation for the products that you have recently purchased in the Document Library.
Very-long-chain fatty acid sphingomyelin in nuclear lipid microdomains of hepatocytes and hepatoma cells: can the exchange from C24: 0 to C16: 0 affect signal proteins and vitamin D receptor?
Lazzarini A, et al.
Molecular Biology of the Cell, 26(13), 2418-2425 (2015)
Phase transitions of highly asymmetric chain-length N-lignocerylsphingomyelin (C24: 0-SM) bilayer
Ohtaka H, et al.
Journal of Thermal Analysis and Calorimetry, 113(3), 1593-1602 (2013)
Mechanical properties of milk sphingomyelin bilayer membranes in the gel phase: Effects of naturally complex heterogeneity, saturation and acyl chain length investigated on liposomes using AFM
Et-Thakafy O, et al.
Chemistry and Physics of Lipids, 210, 47-59 (2018)
Elisabetta Albi et al.
International journal of molecular sciences, 15(7), 11555-11565 (2014-07-01)
Proliferating thyroid cells are more sensitive to UV-C radiations than quiescent cells. The effect is mediated by nuclear phosphatidylcholine and sphingomyelin metabolism. It was demonstrated that proton beams arrest cell growth and stimulate apoptosis but until now there have been
Ebru Afşar et al.
Redox biology, 30, 101430-101430 (2020-01-25)
We aimed to determine sphingolipid levels and examine apoptotic pathways in human retinal pigment epithelial cells (ARPE-19) undergoing endoplasmic reticulum (ER) stress. Cells were treated with tunicamycin (TM) to induce ER stress and tauroursodeoxycholic acid (TUDCA), an ER stress inhibitor
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