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Merck

860063P

Avanti

Milk SM

Avanti Research - A Croda Brand

Synonym(e):

N-(tricosanoyl)-sphing-4-enine-1-phosphocholine

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About This Item

CAS-Nummer:
UNSPSC-Code:
12352211
NACRES:
NA.25

Beschreibung

Sphingomyelin (Milk, Bovine)

Assay

>99% (TLC)

Form

powder

Verpackung

pkg of 1 × 200 mg (860063P-200mg)
pkg of 1 × 25 mg (860063P-25mg)

Hersteller/Markenname

Avanti Research - A Croda Brand

Lipid-Typ

sphingolipids

Versandbedingung

dry ice

Lagertemp.

−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

InChIKey

SXZWBNWTCVLZJN-NMIJJABPSA-N

Allgemeine Beschreibung

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

Anwendung

Milk SM has been used as a lipid standard. It is also suitable for detecting ceramide in feces and for differential scanning calorimetry.

Verpackung

5 mL Amber Glass Screw Cap Vial (860063P-200mg)
5 mL Amber Glass Screw Cap Vial (860063P-25mg)

Rechtliche Hinweise

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Lagerklassenschlüssel

11 - Combustible Solids


Analysenzertifikate (COA)

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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
A relative quantitative positive/negative ion switching method for untargeted lipidomics via high resolution LC-MS/MS from any biological source
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