Oleoylethanolamide

Modify Date: 2024-01-03 10:06:47

Oleoylethanolamide Structure
Oleoylethanolamide structure
 Common Name Oleoylethanolamide
CAS Number 111-58-0 Molecular Weight 325.529
Density 0.9±0.1 g/cm3 Boiling Point 496.4±38.0 °C at 760 mmHg
Molecular Formula C20H39NO2 Melting Point 50-60ºC
MSDS Chinese USA Flash Point 254.0±26.8 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Oleoylethanolamide


Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis.

 Names

Name oleoyl ethanolamide
Synonym More Synonyms

 Oleoylethanolamide Biological Activity

Description Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis.
Related Catalog
Target

Human Endogenous Metabolite

PPAR-α

In Vitro Oleoylethanolamide (OEA), an endogenous PPAR-α ligand, attenuates liver fibrosis targeting hepatic stellate cells. Oleoylethanolamide suppresses TGF-β1 induced hepatic stellate cells (HSCs) activation in vitro via PPAR-α. To assess the impact of Oleoylethanolamide on HSCs activation, the expression levels of α-SMA and Col1a in TGF-β1-stimulated HSCs are examined by qPCR. The mRNA levels of α-SMA and Col1a are markedly induced in the group of CFSC cells with TGF-β1 (5 ng/mL) stimulation for 48h, while the mRNA levels are suppressed when treated with Oleoylethanolamide in a dose-dependent manner. Immunofluorescence and western blot results show that Oleoylethanolamide treatment dose-dependently inhibits the protein expression of α-SMA, the marker of HSC activation. The inhibitory effects of Oleoylethanolamide on HSCs activation are completely blocked by PPAR-α antagonist MK886 (10 μM). Moreover, the mRNA and protein expression levels of PPAR-α are down-regulated with TGF-β1 stimulation, while Oleoylethanolamide treatment restores these changes in dose-dependent manner. In addition, the phosphorylation of Smad 2/3 is upregulated in the presence of TGF-β1 stimulation, consistent with the observed effects on HSC activation, while Oleoylethanolamide (10 μM) reduces the phosphorylation of Smad2/3 in CFSC simulated with TGF-β1[1].
In Vivo Oleoylethanolamide (OEA) can significantly suppress the pro-fibrotic cytokine TGF-β1 negatively regulate genes in the TGF-β1 signaling pathway (α-SMA, collagen 1a, and collagen 3a) in mice models of hepatic fibrosis. Treatment with Oleoylethanolamide (5 mg/kg/day, intraperitoneal injection, i.p.) significantly attenuates the progress of liver fibrosis in both two experimental animal models by blocking the activation of hepatic stellate cells (HSCs)[1].
Cell Assay CFSC, HSC cell lines are first obtained from cirrhotic rat liver, and have a similar phenotype to that of early passage primary HSCs. CFSC cells are cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10% fetal bovine serum (FBS) and 1% penicillin/streptomycin. All cells are cultured in 6-well culture plates under 37°C and 5% CO2 in an incubator. The medium is replaced every two days, and the cells are harvested and diluted at a ratio of 1:3 twice a week. In experiments, HSCs are pretreated with the experimental concentration of Oleoylethanolamide (30 μM, 10 μM, 3 μM) before stimulation with 5 ng/mL TGF-β1. mRNA expression levels of α-SMA (A) and Col1a (B) are analyzed by real-time PCR[1].
Animal Admin Mice[1] The Sv/129 mice and PPAR-α knockout mice are maintained in a room with controlled temperature (21-23°C), humidity (55-60%) and lighting (12 h light/dark cycles) and given water ad libitum. Mice are randomly divided for methionine choline-deficient (MCD) and thioacetamide (TAA) experiments. In the MCD-diet feeding experiment, wild-type Sv/129 mice and PPAR-α knockout mice are each divided into three groups (n=8 /group): (i) control group receive normal diet; (ii) fed with MCD diet and injected with the vehicle (5% Tween-80+5% PEG400+90% saline, 5 mL/kg/day, 8 weeks, intraperitoneal injection, i.p.); (iii) fed with MCD diet along with Oleoylethanolamide administration (5 mg/kg/day; 8 weeks, i.p.). In another set of experiment, all the wild-type mice and PPAR-α knockout mice are given standard chow diet, and are randomly separated into three groups: the control group is not administrated TAA or Oleoylethanolamide but is injected with the saline; the TAA group is injected with TAA (160 mg/kg, three times per week, 6 weeks, dissolved in saline, i.p.) plus the corresponding vehicle; the Oleoylethanolamide group is both injected with TAA and Oleoylethanolamide (5 mg/kg/day; 6 weeks, i.p.)[1].
References

[1]. Chen L, et al. Oleoylethanolamide, an endogenous PPAR-α ligand, attenuates liver fibrosis targeting hepatic stellate cells. Oncotarget. 2015 Dec 15;6(40):42530-40

 Chemical & Physical Properties

Density 0.9±0.1 g/cm3
Boiling Point 496.4±38.0 °C at 760 mmHg
Melting Point 50-60ºC
Molecular Formula C20H39NO2
Molecular Weight 325.529
Flash Point 254.0±26.8 °C
Exact Mass 325.298065
PSA 49.33000
LogP 6.36
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.474
Storage condition −20°C

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant;
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 2

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 Synonyms

Oleic acid ethanolamide
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
MFCD08059579
N-(2-Hydroxyethyl)oleamide
N-(Hydroxyethyl)oleamide N-(cis-9-Octadecenoyl)ethanolamine OEA oleoylethanolamide
N-(9Z-octadecenoyl)-ethanolamine
Oleoyl monoethanolamide
(9Z)-N-(2-hydroxyethyl)octadec-9-enamide
N-oleoyl ethanolamide
Oleoylethanolamide
N-Oleoylethanolamine
9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-
N-Oleoyl-2-aminoethanol
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamide
N-(cis-9-Octadecenoyl)ethanolamine
N-oleoyl ethanolamine
Oleic acid monoethanolamide
EINECS 203-884-8
9Z-octadecenoylethanolamide
Oleoyl Ethanolamide
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