Art. -Nr.: HY-107542

Oleoylethanolamide

(Synonyms: N-Oleoylethanolamide; Oleamide MEA; Oleic acid monoethanolamide)

3 Cited Publications

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

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Reinheit: 98.19%
CAS. Nr.: 111-58-0
Formel: C₂₀H₃₉NO₂
Molecular Weight:325.53

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Oleoylethanolamide Chemical Structure

CAS. Nr.: 111-58-0

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
- Clinical Trial
Chemical Information
Publications (3)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

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

IC₅₀ & Target^[1]

Human Endogenous Metabolite

PPAR-α

Alle Endogenous Metabolite Isoform-spezifische Produkte anzeigen :

Alle PPAR Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
786-0	GI₅₀	35.4 μg/mL Compound: 4c	Antiproliferative activity against human 786-0 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human 786-0 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
HEK293	EC₅₀	0.89 μM Compound: 2a, OEA	Agonist activity on human recombinant TRPV1-mediated enhancement of intracellular calcium concentration in HEK293 cells Agonist activity on human recombinant TRPV1-mediated enhancement of intracellular calcium concentration in HEK293 cells	[PMID: 16570929]
HEK293	EC₅₀	2.2 μM Compound: OEA	Agonist activity at human GPR119 expressed in HEK293 cells assessed as cAMP accumulation after 60 mins Agonist activity at human GPR119 expressed in HEK293 cells assessed as cAMP accumulation after 60 mins	[PMID: 23357035]
HEK293	EC₅₀	2.2 μM Compound: OEA	Agonist activity at human GPR119 expressed in HEK293 cells assessed as stimulation of cAMP level measured after 60 mins by HTRF assay Agonist activity at human GPR119 expressed in HEK293 cells assessed as stimulation of cAMP level measured after 60 mins by HTRF assay	[PMID: 27825553]
HEK293	EC₅₀	2.2 μM Compound: OEA	Agonist activity at human GPR119 expressed in HEK293 cells assessed as increase in cAMP stimulation measured after 60 mins by TR-FRET assay Agonist activity at human GPR119 expressed in HEK293 cells assessed as increase in cAMP stimulation measured after 60 mins by TR-FRET assay	[PMID: 28408218]
HEK293	EC₅₀	2200 nM Compound: OEA	Agonist activity at human GPR119 transfected in HEK293 cells assessed as concentration for 50 % cAMP stimulation of oleylethanolamine Agonist activity at human GPR119 transfected in HEK293 cells assessed as concentration for 50 % cAMP stimulation of oleylethanolamine	[PMID: 23374864]
HEK293	EC₅₀	3.65 μM Compound: 3b, OEA	Agonist activity at human recombinant TRPV1 expressed in HEK293 cells assessed as increase in intracellular calcium level Agonist activity at human recombinant TRPV1 expressed in HEK293 cells assessed as increase in intracellular calcium level	[PMID: 19361197]
HeLa	EC₅₀	0.12 μM Compound: OEA	Transactivation of human Gal4 fused PPARalpha LBD transfected in human HeLa cells after 7 hrs by dual-luciferase reporter gene assay Transactivation of human Gal4 fused PPARalpha LBD transfected in human HeLa cells after 7 hrs by dual-luciferase reporter gene assay	[PMID: 27622746]
HeLa	EC₅₀	1.1 μM Compound: OEA	Transactivation of human Gal4 fused PPARdelta LBD transfected in human HeLa cells after 7 hrs by dual-luciferase reporter gene assay Transactivation of human Gal4 fused PPARdelta LBD transfected in human HeLa cells after 7 hrs by dual-luciferase reporter gene assay	[PMID: 27622746]
MCF7	EC₅₀	152 nM Compound: OEA	Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI DR1-type RE after 16 hrs by luciferase reporter gene assay Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI DR1-type RE after 16 hrs by luciferase reporter gene assay	[PMID: 24936232]
MCF7	EC₅₀	152 nM Compound: OEA	Agonist activity at human PPARalpha transfected in human MCF7 cells after 16 hrs by luciferase reporter gene assay Agonist activity at human PPARalpha transfected in human MCF7 cells after 16 hrs by luciferase reporter gene assay	[PMID: 26226490]
MCF7	EC₅₀	185 nM Compound: OEA	Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI DR1-type RE after 6 hrs by luciferase reporter gene assay Agonist activity at human PPARalpha expressed in MCF7 cells co-transfected CPTI DR1-type RE after 6 hrs by luciferase reporter gene assay	[PMID: 24936232]
MCF7	GI₅₀	25.9 μg/mL Compound: 4c	Antiproliferative activity against human MCF7 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human MCF7 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
NCI/ADR-RES	GI₅₀	9.1 μg/mL Compound: 4c	Antiproliferative activity against human NCI/ADR-RES cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human NCI/ADR-RES cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
NCI-H460	GI₅₀	36.5 μg/mL Compound: 4c	Antiproliferative activity against human NCI-H460 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human NCI-H460 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
OVCAR-3	GI₅₀	35.4 μg/mL Compound: 4c	Antiproliferative activity against human OVCAR3 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human OVCAR3 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
PC-3	GI₅₀	16.9 μg/mL Compound: 4c	Antiproliferative activity against human PC3 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human PC3 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]
RBL-2H3	IC₅₀	>50 μM Compound: 10	Antiallergic activity in rat RBL2H3 cells assessed as inhibition of DNP-HSA-mediated degranulation by measuring decrease in beta-hexosaminidase activity preincubated for 30 mins followed by DNP-HSA stimulation and measured after 30 mins by 4-nitrophenyl 2 Antiallergic activity in rat RBL2H3 cells assessed as inhibition of DNP-HSA-mediated degranulation by measuring decrease in beta-hexosaminidase activity preincubated for 30 mins followed by DNP-HSA stimulation and measured after 30 mins by 4-nitrophenyl 2	[PMID: 31618024]
RBL-2H3	IC₅₀	20 μM Compound: 2a, OEA	Inhibition of AEA uptake in RBL2H3 cells Inhibition of AEA uptake in RBL2H3 cells	[PMID: 16570929]
SK-OV-3	IC₅₀	24 μM Compound: N-oleylethanolamine	Inhibition of ceramidase in human SKOV3 cells assessed as hydrolysis of N-((2S,3R)-1,3-dihydroxy-5-((2-oxo-2H-chromen-7- yl)oxy)pentan-2-yl)palmitamide at 16 uM after 24 hrs at 37 degC by HPLC Inhibition of ceramidase in human SKOV3 cells assessed as hydrolysis of N-((2S,3R)-1,3-dihydroxy-5-((2-oxo-2H-chromen-7- yl)oxy)pentan-2-yl)palmitamide at 16 uM after 24 hrs at 37 degC by HPLC	[PMID: 20085856]
SK-OV-3	IC₅₀	28 μM Compound: N-oleylethanolamine	Inhibition of ceramidase in human SKOV3 cells assessed as hydrolysis of N-((2S,3R)-1,3-dihydroxy-5-((2-oxo-2H-chromen-7- yl)oxy)pentan-2-yl)palmitamide at 16 uM after 24 hrs at 37 degC by umbelliferone formation based fluorescence intensity assay Inhibition of ceramidase in human SKOV3 cells assessed as hydrolysis of N-((2S,3R)-1,3-dihydroxy-5-((2-oxo-2H-chromen-7- yl)oxy)pentan-2-yl)palmitamide at 16 uM after 24 hrs at 37 degC by umbelliferone formation based fluorescence intensity assay	[PMID: 20085856]
U-251	GI₅₀	27.3 μg/mL Compound: 4c	Antiproliferative activity against human U251 cells after 48 hrs by sulforhodamine B assay Antiproliferative activity against human U251 cells after 48 hrs by sulforhodamine B assay	[PMID: 25510639]

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

CAS. Nr. 111-58-0
Appearance Solid
Molecular Weight 325.53
Formel C₂₀H₃₉NO₂
Color White to light yellow
SMILES

CCCCCCCC/C=C\CCCCCCCC(NCCO)=O
Synonyms

N-Oleoylethanolamide; Oleamide MEA; Oleic acid monoethanolamide
Structure Classification
- Others
Initial Source
- Endogenous metabolite
- Human Gut Microbiota Metabolites
- Microorganisms
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (3)

All Bio/Physico-chemical AssayWB

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Journal Impact Factor

Autophagy

Mitophagy-mediated S1P facilitates muscle adaptive responses to endurance exercise through SPHK1-S1PR1/S1PR2 in slow-twitch myofibers. [Abstract]

2025 Apr 3. PMID: 40181214

Oleoylethanolamide purchased from MedChemExpress. Usage Cited in: Autophagy. 2025 Apr 3. [Abstract]

Quantification of S1P concentrations in C2C12 myotubes treated with 10 μM FCCP for 4 h with/without 50 μM NOE or 5 μM SKI-II pre-treatment (n = 4).

Oleoylethanolamide purchased from MedChemExpress. Usage Cited in: Autophagy. 2025 Apr 3. [Abstract]

PPARGC1A protein levels in the C2C12 myotubes 48 h after the stimulation of 10 μM FCCP with/without 50 μM NOE (24 h) in the absence or presence of 5 μM S1P (n = 3).
J Agric Food Chem

Exposure to Succinate Leads to Steatosis in Non-Obese Non-Alcoholic Fatty Liver Disease by Inhibiting AMPK/PPARα/FGF21-Dependent Fatty Acid Oxidation. [Abstract]

2024 Sep 25;72(38):21052-21064. PMID: 39268842

Oleoylethanolamide purchased from MedChemExpress. Usage Cited in: J Agric Food Chem. 2024 Sep 25;72(38):21052-21064. [Abstract]

The PPARα and FGF21 protein expression levels was detected using Western blot after treatment with OEA (10 μM) for 48 h in PA-treated HepG2 cells.
Structure

Native mass spectrometry prescreening of G protein-coupled receptor complexes for cryo-EM structure determination. [Abstract]

2024 Dec 5;32(12):2206-2219.e4. PMID: 39471802

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 20.83 mg/mL (63.99 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.0719 mL

15.3596 mL

30.7191 mL

5 mM

0.6144 mL

3.0719 mL

6.1438 mL

10 mM

0.3072 mL

1.5360 mL

3.0719 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.08 mg/mL (6.39 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.08 mg/mL (6.39 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Protokoll

Cell Assay^[1]

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration^[1]

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].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (272 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[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 [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	3.0719 mL	15.3596 mL	30.7191 mL	76.7978 mL
	5 mM	0.6144 mL	3.0719 mL	6.1438 mL	15.3596 mL
	10 mM	0.3072 mL	1.5360 mL	3.0719 mL	7.6798 mL
	15 mM	0.2048 mL	1.0240 mL	2.0479 mL	5.1199 mL
	20 mM	0.1536 mL	0.7680 mL	1.5360 mL	3.8399 mL
	25 mM	0.1229 mL	0.6144 mL	1.2288 mL	3.0719 mL
	30 mM	0.1024 mL	0.5120 mL	1.0240 mL	2.5599 mL
	40 mM	0.0768 mL	0.3840 mL	0.7680 mL	1.9199 mL
	50 mM	0.0614 mL	0.3072 mL	0.6144 mL	1.5360 mL
	60 mM	0.0512 mL	0.2560 mL	0.5120 mL	1.2800 mL

Keywords

Oleoylethanolamide

3 Cited Publications

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Oleoylethanolamide

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Publications Citing Use of MedChemExpress (MCE) Oleoylethanolamide

Alle Endogenous Metabolite Isoform-spezifische Produkte anzeigen

Alle PPAR Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Publications (3)

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Oleoylethanolamide Related Classifications

HY-107542 Related Classifications