860063P

Milk SM

Avanti Polar Lipids

• Synonym(s): N-(tricosanoyl)-sphing-4-enine-1-phosphocholine
• CAS Number: 475662-40-9
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• 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 Polar Lipids
• 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

Description

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

Safety Information

• Storage Class Code: 11 - Combustible Solids