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S0756

Sphingomyelin

Name: Sphingomyelin
Brand: SIGMA

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

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Properties

biological source

chicken egg yolk

Quality Segment

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

Description

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