CAS Number111-58-0
SynonymsOleic acid ethanolamide; 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; 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
Molecular FormulaC20H39NO2
Molecular Weight325.53
Purity~98 (TLC)%
Density0.9±0.1 g/cm3
Boiling Point496.4±38.0 °C at 760 mmHg
Melting Point50-60ºC
Appearancepowder
EINECS203-884-8
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 111-58-0 |
| Catalog No. | 2A-9011754 |
| Chinese Name | 油酰乙醇胺 |
| Synonyms | Oleic acid ethanolamide; 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; 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 |
| Molecular Formula | C20H39NO2 |
| Molecular Weight | 325.53 |
| Purity | ~98 (TLC) |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 496.4±38.0 °C at 760 mmHg |
| Melting Point | 50-60ºC |
| Appearance | powder |
| Storage Condition | −20°C |
| Application | Oleoylethanolamide is a high-affinity endogenous PPAR-α agonist that plays an important role in the treatment of obesity and atherosclerosis. |
| EINECS | 203-884-8 |
| PubChem ID | 24278603 |
| MDL Number | MFCD00045972 |
| SMILES | 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 |
| NACRES Code | NA.83 |
| UNSPSC | 12352204 |
| Hazard Symbols | Transport |
| MSDS | msds/11754_1_111_58_0.pdf |
| Bioactivity | Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis. Related Catalog Natural Products >> Others Research Areas >> Cardiovascular Disease Research Areas >> Metabolic Disease 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 InChIKey BOWVQLFMWHZBEF-KTKRTIGZSA-N SMILES CCCCCCCC/C=CCCCCCCCC(=O)NCCO Storage condition −20°C |
| Use of | Oleoylethanolamide is a high affinity endogenous PPAR-α agonist, which plays an important role in the treatment of obesity and arteriosclerosis. Properties Articles54 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 Natural Products >> Others Research Areas >> Cardiovascular Disease Research Areas >> Metabolic Disease Human Endogenous Metabolite 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 Molecular Formula C20H39NO2 Exact Mass 325.298065 PSA 49.33000 Index of Refraction 1.474 InChIKey BOWVQLFMWHZBEF-KTKRTIGZSA-N SMILES CCCCCCCC/C=CCCCCCCCC(=O)NCCO |
| Transport Info | Product name: Purity: 0.0% |
| MSDS Transport Info | Module 14. Shipping information European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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