description
Sphingomyelin (Milk, Bovine)
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 200 mg (860063P-200mg), pkg of 1 × 25 mg (860063P-25mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O
InChI
1S/C46H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-28-30-32-34-36-38-40-46(50)47-44(43-54-55(51,52)53-42-41-48(3,4)5)45(49)39-37-35-33-31-29-27-19-17-15-13-11-9-7-2/h37,39,44-45,49H,6-36,38,40-43H2,1-5H3,(H-,47,50,51,52)/b39-37+/t44-,45+/m0/s1
InChI key
SXZWBNWTCVLZJN-NMIJJABPSA-N
General description
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 base. 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 rafts. 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 network.
Sphingomyelin and related lipids
Sphingomyelin and related lipids
Application
Milk SM has been used as a lipid standard. It is also suitable for detecting ceramide in feces and for differential scanning calorimetry.
Packaging
5 mL Amber Glass Screw Cap Vial (860063P-200mg)
5 mL Amber Glass Screw Cap Vial (860063P-25mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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Storage Class
11 - Combustible Solids
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Polymer resonators sensors for detection of sphingolipid gel/fluid phase transition and melting temperature measurement
Li Q, et al.
Sensors and actuators A, Physical, 263, 707-717 (2017)
Neutral ceramidase encoded by the Asah2 gene is essential for the intestinal degradation of sphingolipids
Kono M, et al.
The Journal of biological chemistry, 281(11), 7324-7331 (2006)
Mari Kono et al.
The Journal of biological chemistry, 281(11), 7324-7331 (2005-12-29)
Complex sphingolipids are abundant as eukaryotic cell membrane components, whereas their metabolites, in particular ceramide, sphingosine, and sphingosine 1-phosphate, are involved in diverse cell signaling processes. In mammals, degradation of ceramide by ceramidase yields sphingosine, which is phosphorylated by the
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 860063P-200MG | 04061835316854 |
| 860063P-25MG | 04061835316861 |