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S0756

Sigma-Aldrich

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

biological source

chicken egg yolk

Quality Level

200

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

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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.

Quality

Contains primarily palmitic acid.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
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
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
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
View All Related Papers

Protocols

LC/MS Analysis of Phospholipids in Milk on Ascentis® Express HILIC after SPE using Supelclean™ Si, Shotgun HPLC Analysis

(soybean), ≥97%; L-α-Phosphatidylethanolamine from egg yolk, Type III, ≥97% (TLC), lyophilized powder; L-α-Phosphatidylcholine, from egg yolk, Type XVI-E, ≥99% (TLC), lyophilized powder; Sphingomyelin, from chicken egg yolk, ≥95%

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