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Merck

860063C

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
MDL number:
MFCD28143627
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

Milk SM, Avanti Research™ - A Croda Brand

SMILES string

[P](=O)([O-])(OC[C@H](NC(=O)CCCCCCCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)OCC[N+](C)(C)C

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

description

Sphingomyelin (Milk, Bovine), chloroform

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (860063C-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL (860063C-25mg)

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

Milk SM is suitable:
  • for detecting ceramide in feces
  • for differential scanning calorimetry
  • as a lipid standard

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

Packaging

5 mL Clear Glass Sealed Ampule (860063C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system

wgk

WGK 3

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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
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)
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
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