S8439
Stearoyl ethanolamide
≥98%, crystalline
Synonym(s):
N-Stearoylethanolamine, NSE
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About This Item
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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 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
Certificates of Analysis (COA)
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Polymorphism of N-stearoylethanolamine: differential scanning calorimetric, vibrational spectroscopic (FTIR), and crystallographic studies
Chemistry and Physics of Lipids, 119(1), 13-21 (2002)
Archives of biochemistry and biophysics, 434(2), 344-351 (2005-01-11)
The effects of saturated long-chain (C: 16-22) N-acylethanolamines and a series of saturated fatty acids with the same length of carbon chains were investigated on depolarization-induced (45)Ca(2+) fluxes mediated by voltage-dependent Ca(2+) channels in transverse tubule membrane vesicles from rabbit
Effects of N-stearoylethanolamine on anxiety-like behavioral reactions of rats after chronic alcoholization
Biologija, 60(1) (2014)
Structure and phase behavior of O-stearoylethanolamine: A combined calorimetric, spectroscopic and X-ray diffraction study
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
International Immunopharmacology, 52, 290-296 (2017)
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