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860063P

Avanti

Milk SM

Avanti Research™ - A Croda Brand

Synonym(s):

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

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About This Item

CAS Number:
475662-40-9
UNSPSC Code:
12352211
NACRES:
NA.25

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

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

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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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)
S Jyonouchi et al.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 44(1), 58-68 (2013-10-15)
Eosinophilic esophagitis (EoE) is an atopic disease characterized by eosinophilic inflammation in which dietary antigens (in particular, milk) play a major role. EoE is most likely a mixed IgE and non-IgE food-mediated reaction in which overexpression of Th2 cytokines, particularly
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
Breitkopf S B, et al.
Metabolomics, 13(3), 30-30 (2017)
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