860062C

Brain SM

Avanti Research^™ - A Croda Brand

• Synonym(s): 18:0 SM; Octadecanoyl Sphingomyelin; N-octadecanoyl-D-erythro-sphingosylphosphorylcholine; N-(octadecanoyl)-sphing-4-enine-1-phosphocholine
• CAS Number: 383907-91-3
• MDL number: MFCD02259130
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• description: Sphingomyelin (Brain, Porcine), chloroform
• Assay: >99% (TLC)
• form: liquid
• packaging: pkg of 1 × 2.5 mL (860062C-25mg); pkg of 2 × 4 mL (860062C-200mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand
• concentration: 10 mg/mL (860062C-25mg); 25 mg/mL (860062C-200mg)
• lipid type: sphingolipids
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: [P](=O)([O-])(OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)OCC[N+](C)(C)C
• InChI: 1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1
• InChI key: LKQLRGMMMAHREN-YJFXYUILSA-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.[1] 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.[1] 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.[1]
Sphingomyelin and related lipids

Application

Brain SM may be used:

• for ion-mobility spectrometry–mass spectrometry (IMS-MS)[2]
• for lipid mixture in giant unilamellar vesicles[3]
• as a growth medium for madin-darby canine kidney (MDCK) cells[4]

Packaging

5 mL Clear Glass Sealed Ampule (860062C-200mg)

5 mL Clear Glass Sealed Ampule (860062C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H302,H315,H319,H331,H336,H351,H361d,H372,H412
• Precautionary Statements: P201 - P273 - P301 + P312 + P330 - P302 + P352 - P304 + P340 + P311 - P308 + P313
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3
• Target Organs: Central nervous system, Liver,Kidney
• WGK: WGK 3