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Merck

S8439

Sigma-Aldrich

Stearoyl ethanolamide

≥98%, crystalline

Sinónimos:

N-Stearoylethanolamine, NSE

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About This Item

Fórmula empírica (notación de Hill):
C20H41NO2
Número de CAS:
Peso molecular:
327.55
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83

Quality Level

assay

≥98%

form

crystalline

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCCC(=O)NCCO

InChI

1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)

Inchi Key

OTGQIQQTPXJQRG-UHFFFAOYSA-N

Gene Information

rat ... Cnr1(25248)

General description

Stearoyl ethanolamide, also called N-stearoylethanolamine (NSE) is present ubiquitously in all mammals. It exists in three isoforms when synthesized. It has therapeutic potential to modulate immune and inflammatory responses. It also possess antioxidative and membranoprotective functionality. NSE molecules pack in tail-to-tail fashion in lipid bilayer.

Application

Stearoyl ethanolamide (NSE) has been used as standard for quantifying in house synthesized NSE using thin layer chromatography.

Biochem/physiol Actions

Most abundant fatty acid ethanolamide produced by PLD hydrolysis of cell membrane phospholipids.

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)


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PloS one, 6(11), e27257-e27257 (2011-11-30)
N-acylethanolamines (NAEs) are endogenous compounds that regulate inflammation and pain. These include the cannabinoid ligand anandamide (AEA) and the peroxisome proliferator-activated receptor-α ligand palmitoylethanolamide (PEA). Little is known as to the levels of NAEs in pain states in human, particularly
Structure and phase behavior of O-stearoylethanolamine: A combined calorimetric, spectroscopic and X-ray diffraction study
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Biochimica et Biophysica Acta - Biomembranes, 1798(5), 872-881 (2010)
n-stearoylethanolamine protects the brain and improves memory of mice treated with lipopolysaccharide or immunized with the extracellular domain of alpha7 nicotinic acetylcholine receptor
Lykhmus O, et al.
International Immunopharmacology, 52, 290-296 (2017)
Mauro Maccarrone et al.
The Biochemical journal, 366(Pt 1), 137-144 (2002-05-16)
Stearoylethanolamide (SEA) is present in human, rat and mouse brain in amounts comparable with those of the endocannabinoid anandamide (arachidonoylethanolamide; AEA). Yet, the biological activity of SEA has never been investigated. We synthesized unlabelled and radiolabelled SEA to investigate its

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