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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

Key Documents

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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)

Related Categories

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

General description

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

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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Xiaotong Diao et al.
Nature communications, 13(1), 2529-2529 (2022-05-10)
Hypoxia-inducible factors (HIFs) are α/β heterodimeric transcription factors modulating cellular responses to the low oxygen condition. Among three HIF-α isoforms, HIF-3α is the least studied to date. Here we show that oleoylethanolamide (OEA), a physiological lipid known to regulate food
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
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)
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
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