O0383

N-Oleoylethanolamine

~98% (TLC)

• Synonym(s): N-(Hydroxyethyl)oleamide, N-(cis-9-Octadecenoyl)ethanolamine, OEA, oleoylethanolamide
• 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

Properties

• 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)

Description

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 2
• ppe: dust mask type N95 (US), Eyeshields, Gloves