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Merck
CN

S7004

Sphingomyelin

from bovine brain, ≥97.0%, powder

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
UNSPSC Code:
12352211
MDL number:
MFCD00132361

Key Documents

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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

bovine brain

assay

≥97.0%

form

powder

color

white

storage temp.

−20°C

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Application

Sphingomyelin was used as exogenous treatment to study the effect on ATP depletion and Fe-mediated cell injury in human proximal tubular cell line, HK-2 cells.3 It was used to study the effect on Akt phosphorylation in obese mice.4

Biochem/physiol Actions

Sphingomyelin (SM) is a sphingolipid found in the myelin sheath and cell membranes of animals. The regulation of SM content by sphingomyelinase and SM synthase 2 affect the membrane properties and signaling.1 Excess oxysterols result in increased amount of SM and calcium ions that is the main reason for artery blockage and atherosclerosis.2

Other Notes

Contains primarily stearic, nevonic, and lignoceric acids.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
070M1977
099K1214
099K1024
049K1148
108K0967

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N A Babenko et al.
Biochemistry. Biokhimiia, 64(8), 912-915 (1999-09-28)
Inhibition of thyroid gland function in rats with mercasolil sharply decreased thyroxine and triiodothyronine levels in blood serum and increased acid sphingomyelinase activity and sphingomyelin content in liver. Thyroxine injected into hypothyroid rats normalized the sphingomyelin content, reduced the free
I Bankov et al.
Folia parasitologica, 45(4), 257-260 (1998-12-30)
Sphingolipids are a diverse and ubiquitous group of lipids. They are widely distributed in parasites and a number of novel forms have been described. Sphingolipid synthesis has been investigated in the malarial parasite, cestodes, digeneans and nematodes. Although there are

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