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MilliporeSigma

860061P

Avanti

Egg SM

Avanti Research - A Croda Brand

Synonyme(s) :

16:0 SM; Hexadecanoyl Sphingomyelin; N-hexadecanoyl-D-erythro-sphingosylphosphorylcholine; N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine; Sphingomyelin (Egg, Chicken)

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A propos de cet article

Numéro CAS:
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
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description

Sphingomyelin (Egg, Chicken)

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 g (860061P-1g), pkg of 1 × 200 mg (860061P-200mg), pkg of 1 × 25 mg (860061P-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(CCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O

InChI

1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

InChI key

RWKUXQNLWDTSLO-GWQJGLRPSA-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

Egg SM has been used for the preparation of sphingomyelin (SM) standard solutions. It has also been used in the preparation of liposomes.

Packaging

20 mL Clear Glass Screw Cap Vial (860061P-1g)
5 mL Amber Glass Screw Cap Vial (860061P-200mg)
5 mL Amber Glass Screw Cap Vial (860061P-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC


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Protocols for Enzymatic Fluorometric Assays to Quantify Phospholipid Classes
Morita S, et al.
International Journal of Molecular Sciences, 21(3), 1032-1032 (2020)
Visualization of the two-step fusion process of the retrovirus avian sarcoma/leukosis virus by cryo-electron tomography
Cardone G, et al.
Journal of Virology, 86(22), 12129-12137 (2012)
Maia Kinnebrew et al.
eLife, 8 (2019-10-29)
Previously we proposed that transmission of the hedgehog signal across the plasma membrane by Smoothened is triggered by its interaction with cholesterol (Luchetti et al., 2016). But how is cholesterol, an abundant lipid, regulated tightly enough to control a signaling



Numéro d'article de commerce international

RéférenceGTIN
860061P-200MG04061835316793
860061P-1G04061835316786
860061P-25MG04061835316809