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Merck

S0756

Sphingomyelin

from chicken egg yolk, ≥95%

Synonym(s):

N-Acyl-4-sphingenyl-1-O-phosphorylcholine, N-Acyl-D-sphingosine-1-phosphocholine

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About This Item

CAS Number:
85187-10-6
UNSPSC Code:
12352211
NACRES:
NA.25
EC Number:
286-097-2
MDL number:
MFCD00132361

Product Name

Sphingomyelin, from chicken egg yolk, ≥95%

InChI key

LRYZPFWEZHSTHD-HEFFAWAOSA-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

SMILES string

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

biological source

chicken egg yolk

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

Quality Level

200

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Analysis Note

Contains primarily palmitic acid.

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.

General description

Sphingomyelin (SM) is a principal sphingolipid in mammalian cell membranes. Its biological functions have been studied.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000417443
0000417443
0000394834
0000374062
0000374060

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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
Biological functions of sphingomyelins.
Slotte JP.
Progress in Lipid Research, 52(4), 424-437 (2013)
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
D E Freer et al.
Clinical chemistry, 24(11), 1980-1984 (1978-11-01)
We evaluated the relative contributions of various phospholipids to the formation of foam in the amniotic fluid "foam stability test", by use of an artificial system of saline, ethanol, and dipalmitoyl 3-sn-phosphatidylcholine to determine the relationship between dipalmitoyl 3-sn-phosphatidylcholine concentration
J C Russell
Clinical chemistry, 33(7), 1177-1184 (1987-07-01)
The mechanism of a new fluorescence polarization method for measuring phospholipid in amniotic fluid is described. The fluorescence polarization of a surfactant fluorescent dye solubilized in amniotic fluid correlates significantly with the L/S ratio. Model studies indicate that this results
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