biological source
chicken egg yolk
Quality Level
assay
≥95%
form
powder
solubility
chloroform/methanol: soluble 50 mg/mL, clear, colorless to faintly yellow (1:1)
functional group
phospholipid
lipid type
sphingolipids
shipped in
ambient
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC=O)COP(O)(OCC[N+](C)(C)C)=O)O
InChI
1S/C24H49N2O6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(28)23(25-22-27)21-32-33(29,30)31-20-19-26(2,3)4/h17-18,22-24,28H,5-16,19-21H2,1-4H3,(H-,25,27,29,30)/p+1/b18-17+/t23-,24+/m0/s1
InChI key
LRYZPFWEZHSTHD-HEFFAWAOSA-O
General description
Sphingomyelin (SM) is a principal sphingolipid in mammalian cell membranes. Its biological functions have been studied.
Application
Sphingomyelin is suitable for use:
- in the preparation of standard during the enzymatic measurement of plasma sphingomyelin levels
- to study the binding of Vascular Anticoagulant α (VAC α) to planar phospholipid bilayers
- to perform fluorescence polarization of PC16 (N-[α-N-palmitoyl-ε-N-(4-nitrobenz-2-oxa-1,3-diazole)-L-lysine]-2-aminoethanol-N- (trimethylaminoethanol) phosphate) in dispersions of co-sonicated lecithin and sphingomyelin
- for reconstitution of viral ion channel protein M2 into liposomes
- as a standard sample to define spectral fingerproint using Time-of-flight secondary ion mass spectrometry (ToF-SIMS)
- to evaluate the contribution of various phospholipids to the formation of foam in the amniotic fluid
Biochem/physiol Actions
Sphingomyelin is the second most abundant lipid and major sphingolipid component of HDL and the plasma membrane. It forms cholesterol-enriched lipid rafts. It has a key role in the availability of plasma membrane-free cholesterol.
Analysis Note
Contains primarily palmitic acid.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Biological functions of sphingomyelins.
Slotte JP.
Progress in Lipid Research, 52(4), 424-437 (2013)
H A Andree et al.
The Journal of biological chemistry, 265(9), 4923-4928 (1990-03-25)
Vascular anticoagulant alpha (VAC alpha, annexin V) is a member of the family of calcium and phospholipid binding proteins, the annexins. The binding properties of VAC alpha to phospholipid bilayers were studied by ellipsometry. Adsorption was calcium-dependent and completely reversible
Mohammad Reza Hojjati et al.
Journal of lipid research, 47(3), 673-676 (2005-12-24)
Sphingomyelin (SM) and phosphatidylcholine (PC) are two major phospholipids on plasma lipoproteins. Their concentration is classically measured by lipid extraction, thin-layer chromatography, and phosphate determination on separated SM or PC spots. Here, we describe two rapid, specific, and sensitive enzymatic