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T1014

Sigma-Aldrich

TNPAL-Sphingomyelin

1 mg/mL in chloroform/methanol (2:1)

Synonym(s):

Trinitrophenylaminolauroylsphingomyelin

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About This Item

Empirical Formula (Hill Notation):
C41H73N6O12P
CAS Number:
117985-56-5
Molecular Weight:
873.03
MDL number:
MFCD00133879
UNSPSC Code:
12352211
PubChem Substance ID:
24899923

assay

≥98% (TLC)

form

liquid

concentration

1 mg/mL in chloroform/methanol (2:1)

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](COP(O)(=O)OCC[N](C)(C)C)NC(=O)CCCCCCCCCCCNc1c(cc(cc1N(=O)=O)N(=O)=O)N(=O)=O

InChI

1S/C41H74N6O12P/c1-5-6-7-8-9-10-11-12-13-15-18-21-24-27-39(48)36(34-59-60(56,57)58-31-30-47(2,3)4)43-40(49)28-25-22-19-16-14-17-20-23-26-29-42-41-37(45(52)53)32-35(44(50)51)33-38(41)46(54)55/h24,27,32-33,36,39,42,48H,5-23,25-26,28-31,34H2,1-4H3,(H,43,49)(H,56,57)/b27-24+

InChI key

ZAKSUDRQGDIXGH-SOYKGTTHSA-N

Application

TNPAL-Sphingomyelin was used as substrate to determine the activity of sphingomyelinase spectrophotometrically.[1][2][3]

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.[4] Excess oxysterols result in increased amount of SM and calcium ions that is the main reason for artery blockage and atherosclerosis.[5]

Substrates

Substrate for microbial and animal sphingomyelinases.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 1 - STOT SE 3

target_organs

Central nervous system, Eyes

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

51.8 °F - closed cup

flash_point_c

11 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
073M4030V
14120811
015M4049V
14141001
019K4054

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S Gatt et al.
Biochimica et biophysica acta, 530(3), 503-507 (1978-09-28)
A colored derivative of sphingomyelin was synthesized and used as substrate for several sphingomyelinases. The compound is N-omega-trinitrophenyl-aminolaurylsphingosylphosphorylcholine. The rate of hydrolysis of this substrate was compared to that of bovine brain sphingomyelin, labelled with tritium in the choline moiety.
W Vollmer et al.
Molecular microbiology, 39(6), 1610-1622 (2001-03-22)
Streptococcus pneumoniae is a major human pathogen and many interactions of this bacterium with its host appear to be mediated, directly or indirectly, by components of the bacterial cell wall, specifically by the phosphorylcholine residues which serve as anchors for
Fred A Kummerow
American journal of cardiovascular disease, 3(1), 17-26 (2013-03-06)
Despite major public health efforts, coronary heart disease continues to be the leading cause of death in the United States. Oxidized lipids contribute to heart disease both by increasing deposition of calcium on the arterial wall, a major hallmark of
A Dobrzyń et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 55(2), 305-313 (2004-06-24)
The sphingomyelin signalling pathway has been shown to function in different skeletal muscle types. The aim of the present study was to examine the effect of endurance training on the functioning of the pathway in the muscles. The experiments were
Yukinori Taniguchi et al.
Biochimica et biophysica acta, 1758(2), 145-153 (2006-04-04)
To understand the role of sphingomyelinase (SMase) in the function of biological membranes, we have investigated the effect of conversion of sphingomyelin (SM) to ceramide (Cer) on the assembly of domains in giant unilamellar vesicles (GUVs). The GUVs were prepared
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