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860580C

Avanti

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

Avanti Research™ - A Croda Brand 860580C

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

liquid

packaging

pkg of 1 × 1 mL (860580C-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 860580C

concentration

5 mg/mL (860580C-5mg)

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 (SM) is a major constituent of cell membranes.[1] It is present mainly in the membranes of nerve cells (in the myelin sheaths) and red blood cells.[2] SM contains a ceramide unit with a phosphorylcholine moiety attached to position 1.[3]

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.[1]

Biochem/physiol Actions

Sphingomyelin (SM) has a high affinity for cholesterol. Both together regulate the localization and interactions of proteins.[2] SM acts as a precursor to ceramides and other sphingolipid metabolites. It aids iron transport into cells. SM regulates ion channels and receptors.[3]

Packaging

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

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

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SPHINGOMYELIN AND RELATED LIPIDS
OH, H
Journal of the American Oil Chemists' Society null
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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