S0756

Sphingomyelin

from chicken egg yolk, ≥95%

• Synonym(s): N-Acyl-4-sphingenyl-1-O-phosphorylcholine, N-Acyl-D-sphingosine-1-phosphocholine
• CAS Number: 85187-10-6
• EC Number: 286-097-2
• MDL number: MFCD00132361
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• 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

Description

General description

Sphingomyelin (SM) is a principal sphingolipid in mammalian cell membranes. Its biological functions have been studied.[1]

Application

Sphingomyelin is suitable for use:

• in the preparation of standard during the enzymatic measurement of plasma sphingomyelin levels[2]
• to study the binding of Vascular Anticoagulant α (VAC α) to planar phospholipid bilayers[3]
• 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[4]
• for reconstitution of viral ion channel protein M2 into liposomes[5]
• as a standard sample to define spectral fingerproint using Time-of-flight secondary ion mass spectrometry (ToF-SIMS)[6]
• to evaluate the contribution of various phospholipids to the formation of foam in the amniotic fluid[7]

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.[8]

Quality

Contains primarily palmitic acid.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves