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O0383

Sigma-Aldrich

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
EC Number:
203-884-8
MDL number:
MFCD00045972
UNSPSC Code:
12352204
PubChem Substance ID:
24278603
NACRES:
NA.83

Key Documents

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Product Name

N-Oleoylethanolamine, ~98% (TLC)

assay

~98% (TLC)

Quality Level

200

form

powder

solubility

chloroform: 20 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

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

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

Gene Information

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

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_germany

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCF2260
089K5202
067K5200
083H8482

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Sandrine Lecour et al.
Journal of molecular and cellular cardiology, 34(5), 509-518 (2002-06-12)
TNF alpha administration mimics ischemic preconditioning and neutralizing antibodies to TNF alpha and IL-1 beta abolish exercise-induced preconditioning. However, the pharmacology of TNF alpha's cardioprotective effects and associated downstream signaling events has not been delineated. We evaluated the temporal and
Byung-Koo Son et al.
Nanomaterials (Basel, Switzerland), 9(7) (2019-07-13)
A mixture of nanothin exfoliated (NTE) graphite and urea (CO(NH2)2) powder was treated with radio frequency (RF) thermal plasma to achieve in situ purification and nitrogen doping of NTE graphite using the high-temperature flame of the RF plasma. Reactive species
Oleoylethanolamide modulates glucagon-like peptide-1 receptor agonist signaling and enhances exendin-4-mediated weight loss in obese mice
Brown JD, et al.
American Journal of Physiology. Regulatory, Integrative and Comparative Physiology, 315(4), R595-R608 (2018)
The Gastrointestinal Tract and Control of Food Intake
Physiology of the Gastrointestinal Tract, 2, 1963-1978 (2012)
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
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