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O0383

N-Oleoylethanolamine

~98% (TLC), PPARα agonist, powder

Synonym(s):

N-(Hydroxyethyl)oleamide, N-(cis-9-Octadecenoyl)ethanolamine, OEA, oleoylethanolamide

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About This Item

Empirical Formula (Hill Notation):
C20H39NO2
CAS Number:
111-58-0
Molecular Weight:
325.53
NACRES:
NA.83
PubChem Substance ID:
24278603
UNSPSC Code:
12352204
EC Number:
203-884-8
MDL number:
MFCD00045972

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Product Name

N-Oleoylethanolamine, ~98% (TLC)

InChI

1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

InChI key

BOWVQLFMWHZBEF-KTKRTIGZSA-N

SMILES string

O=C(CCCCCCC/C=C\CCCCCCCC)NCCO

assay

~98% (TLC)

form

powder

solubility

chloroform: 20 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Gene Information

human ... CNR1(1268), CNR2(1269), PPARA(5465), TRPV1(7442)
mouse ... Cnr2(12802)
rat ... Cnr1(25248)

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General description

Oleoylethanolamide (OEA) is an endogenous fatty acid ethanolamine. Small intestine cells, adipose tissues, neurons and astrocytes produces OEA.

Application

N-Oleoylethanolamine has been used to study its effects on glucagon-like peptide (GLP)-1RA-mediated anorectic signaling and weight loss.

Biochem/physiol Actions

Oleoylethanolamide (OEA) is a lipid mediator, which helps to control various biological functions, like food intake. It modulates the gene expression in the small intestine. OEA has the ability to initiate several receptors, such as cannabinoid receptor type 1 (CB1), peroxisome proliferator-activated receptors (PPARs) and G protein-coupled receptor 119 (GPR119).
Peroxisome proliferator-activator receptor α (PPARα) agonist

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000443026
0000443046
0000443046
0000443026
0000339364

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The Neurotrophic Effect of Oleic Acid: Implications for Olive Oil in Health and Disease
Olives and Olive Oil in Health and Disease Prevention, 1405-1412 (2010)
Gustavo Provensi et al.
The international journal of neuropsychopharmacology, 20(5), 392-399 (2017-03-25)
The integrity of the brain histaminergic system is necessary for the unfolding of homeostatic and cognitive processes through the recruitment of alternative circuits with distinct temporal patterns. We recently demonstrated that the fat-sensing lipid mediator oleoylethanolamide indirectly activates histaminergic neurons
Lea Tischmann et al.
Nutrients, 12(5) (2020-05-28)
An unfavorable lipid profile and being overweight are known mediators in the development of cardiovascular disease (CVD) risk. The effect of diet, particularly high in protein, remains under discussion. Therefore, this study examines the effects of a high-protein (HP) diet
Tom H Johnston et al.
The Journal of pharmacology and experimental therapeutics, 336(2), 423-430 (2010-10-23)
Dopaminergic therapies remain the most efficacious symptomatic treatments for Parkinson's disease (PD) but are associated with motor complications, including dyskinesia, and nonmotor complications, such as psychosis, impulse control disorders (ICD), and dopamine dysregulation syndrome (DDS). Nondopaminergic neurotransmitter systems, including the
The Gastrointestinal Tract and Control of Food Intake
Physiology of the Gastrointestinal Tract, 2, 1963-1978 (2012)
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