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860580P

Avanti

02:0 SM (d18:1/2:0)

Avanti Research™ - A Croda Brand 860580P, powder

Synonym(s):

N-acetyl-D-erythro-sphingosylphosphorylcholine

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About This Item

Empirical Formula (Hill Notation):
C25H51N2O6P
CAS Number:
148306-05-2
Molecular Weight:
506.66
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (860580P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860580P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C25H51N2O6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(29)24(26-23(2)28)22-33-34(30,31)32-21-20-27(3,4)5/h18-19,24-25,29H,6-17,20-22H2,1-5H3,(H-,26,28,30,31)/b19-18+/t24-,25+/m0/s1

InChI key

GTZSEZHHSPWFFN-WHUSYDGZSA-N

General description

Sphingomyelin is abundantly present in the cell membranes, particularly in myelin sheath and red blood cells. It has a ceramide unit with a phosphorylcholine moiety linked to position 1.

Application

02:0 SM (d18:1/2:0) is suitable for use in liposomes to measure ostreolysin A (OlyA) binding in order to infer the effects of phosphatidylcholines (PCs) on sphingomyelin (SM)/cholesterol interactions.

Biochem/physiol Actions

Sphingomyelin (SM) has high cholesterol affinity, which aids localization and interactions of proteins. It functions as a precursor to ceramides and other sphingolipid metabolites.

Packaging

5 mL Clear Glass Sealed Ampule (860580P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ceramide and neurodegeneration: susceptibility of neurons and oligodendrocytes to cell damage and death
Jana A, et al.
Journal of the Neurological Sciences, 278(1-2), 5-15 (2009)
Molecular discrimination between two conformations of sphingomyelin in plasma membranes
Endapally S, et al.
Cell, 176(5), 1040-1053 (2019)
Delphine Milhas et al.
FEBS letters, 584(9), 1887-1894 (2009-10-28)
The plasma membrane (PM) is a major resource for production of bioactive lipids and contains a large proportion of the cellular sphingomyelin (SM) content. Consequently, the regulation of SM levels at the PM by enzymes such as sphingomyelinase (SMase) and

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