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Merck
CN

860062P

Avanti

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

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About This Item

CAS Number:
383907-91-3
MDL number:
MFCD02259130
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

Brain SM, Avanti Research™ - A Croda Brand

SMILES string

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O

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

Sphingomyelin (Brain, Porcine)

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (860062P-1g)
pkg of 1 × 200 mg (860062P-200mg)
pkg of 1 × 25 mg (860062P-25mg)
pkg of 1 × 500 mg (860062P-500mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

Brain SM is suitable:
  • as a standard for high-performance liquid chromatography electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS)
  • as a supplement for cell vacuolation of Hela cells
  • for preparation of liposomes

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

20 mL Clear Glass Screw Cap Vial (860062P-500mg)
5 mL Amber Glass Screw Cap Vial (860062P-200mg)
5 mL Amber Glass Screw Cap Vial (860062P-25mg)
60 mL Amber Wide Mouth Screw Cap Glass Bottle (860062P-1g)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

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Sphingomyelin functions as a novel receptor for Helicobacter pylori VacA
Gupta VR, et al.
PLoS Pathogens, 4(5), e1000073-e1000073 (2008)
Lipid raft components cholesterol and sphingomyelin increase H+/OH- permeability of phosphatidylcholine membranes
Gensure R H, et al.
The Biochemical Journal, 398(3), 485-495 (2006)
Distinct disruptions in Land's cycle remodeling of glycerophosphocholines in murine cortex mark symptomatic onset and progression in two Alzheimer's disease mouse models
Granger M W, et al.
Journal of Neurochemistry (2018)
Valerija Vezočnik et al.
Langmuir : the ACS journal of surfaces and colloids, 34(30), 8983-8993 (2018-07-10)
Understanding of the interactions between proteins and natural and artificially prepared lipid membrane surfaces and embedded nonpolar cores is important in studies of physiological processes and their pathologies and is applicable to nanotechnologies. In particular, rapidly growing interest in cellular
Yusuke Sato et al.
Acta biomaterialia, 102, 341-350 (2019-11-17)
Despite the fact that small-sized lipid nanoparticles (LNPs) are important for improved tissue penetration and efficient drug delivery, their poor stability and intracellular trafficking significantly hinders their use as potent small-sized LNPs. It has been reported that both the diffusion
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