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O0383

Sigma-Aldrich

N-Oleoylethanolamine

~98% (TLC)

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

Assay

~98% (TLC)

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 Code

11 - Combustible Solids

WGK

WGK 2

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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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
The Gastrointestinal Tract and Control of Food Intake
Physiology of the Gastrointestinal Tract, 2, 1963-1978 (2012)
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)
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
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