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Key Documents

S8439

Sigma-Aldrich

Stearoyl ethanolamide

≥98%, crystalline

Synonym(s):

N-Stearoylethanolamine, NSE

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About This Item

Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
Molecular Weight:
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 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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Polymorphism of N-stearoylethanolamine: differential scanning calorimetric, vibrational spectroscopic (FTIR), and crystallographic studies
Wouters J, et al.
Chemistry and Physics of Lipids, 119(1), 13-21 (2002)
Murat Oz et al.
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
Nazdar Ghafouri et al.
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
Effects of N-stearoylethanolamine on anxiety-like behavioral reactions of rats after chronic alcoholization
Bondarenko OV, et al.
Biologija, 60(1) (2014)
Structure and phase behavior of O-stearoylethanolamine: A combined calorimetric, spectroscopic and X-ray diffraction study
Tarafdar PK and Swamy MJ
Biochimica et Biophysica Acta - Biomembranes, 1798(5), 872-881 (2010)

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