Oleoylethanolamide

HCID 5283454
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
111-58-0
Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCO
InChIKey
BOWVQLFMWHZBEF-KTKRTIGZSA-N
Molecular formula
C20H39NO2
Average molar mass
325.5 g/mol
Monoisotopic mass
325.29807949

Overview

Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a geroprotector, a PPARalpha agonist and an EC 3.5.1.23 (ceramidase) inhibitor. It is a N-acylethanolamine 18:1, a N-(long-chain-acyl)ethanolamine and an endocannabinoid. It is functionally related to an oleic acid.

Names & identifiers

Preferred name
Oleoylethanolamide
IUPAC
(Z)-N-(2-hydroxyethyl)octadec-9-enamide
English name
Oleoyl Ethanolamide
Molecular formula
C20H39NO2
Molecular weight
325.53

Names & synonyms

oleoylethanolamide111-58-0N-(2-Hydroxyethyl)oleamideOleoyl Ethanolamide(Z)-N-(2-hydroxyethyl)octadec-9-enamideOleoyl monoethanolamideOLEIC MONOETHANOLAMIDEN-(9Z-octadecenoyl)-ethanolamine1HI5J9N8E69-Octadecenamide, N-(2-hydroxyethyl)-DTXSID1044516N-(cis-9-octadecenoyl) ethanolamine
Show more names
ODAOEAOleoylethanolamide(OEA)OLEAMIDE MEAN-(Hydroxyethyl)oleamideAM-3101UNII-1HI5J9N8E6
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-CHEBI:71466RefChem:856533DTXCID9024516203-884-8Oleoylethanolaminen-oleoylethanolamineOleylethanolamide

Database identifiers

CAS
111-58-0
PubChem CID
5283454
DTXSID
DTXSID1044516
ChEMBL
CHEMBL280065
ChEBI
CHEBI:71466
UNII
1HI5J9N8E6
EC Number
203-884-8、921-073-3
Nikkaji
J193.596H

Properties

Computed structural properties

XLogP
6.3
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
17
Heavy atoms
23

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Cosmetics · 3 items

Cosmetic ingredients (Oleamide MEA) -> CIR (Cosmetic Ingredient Review)

Personal care product

Antistatic; Viscosity controlling; Foam boosting

Physical Description · 2 items

Other Solid

Solid

Collision Cross Section192.94 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]

Physicochemical properties

Melting point
63 · 63-64 °C
Boiling point
496.4 · 496.4±38.0 °C(Predicted)
Density
0.915 · 0.915±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
solubility
Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 35 mg/ml)
form
White solid

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 205 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: 9-Octadecenamide, N-(2-hydroxyethyl)-, (Z)-

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19715

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Toxicity Summary · 2 items

The CIR Expert Panel concluded that the ethanolamides listed subsequently are safe in the present practices of use and concentration described in this safety assessment when formulated to be non-irritating. The Expert Panel cautioned that these ingredients should not be used in cosmetic products in which N-nitroso compounds may be formed...Oleamide MEA...

Safe for use in cosmetics, with qualifications

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
risk_code
36/37/38
Signal word
Danger
Symbol(GHS)
GHS09,GHS05

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Oleoylethanolamide (OEA) is a major N-acylethanolamine and an endogenous ethanolamide fatty acid. Although it is an endocannabinoids-like compound, it does not bind to cannabinoid receptors. Instead, this lipid sensor is an agonist at peroxisome proliferator-activated receptor-α (PPAR-α) agonist while also being an inhibitor of ceramidase and thereby the sphingolipid signaling pathway.

Tissue LocationsPlacenta
Cellular LocationsExtracellular

Uses & manufacturing

UsesCIR ingredient: Oleamide MEA
U.S. Production2023: 75,000 - <500,000 lb
Consumer UsesSurfactant (surface active agent)
Industry UsesSurfactant (surface active agent)
Use ClassificationCosmetics -> Antistatic; Viscosity controlling; Foam boosting
General Manufacturing Information · 2 items

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: ACTIVE

Applications · 3 items

DescriptionOleoyl ethanolamide (OEA) is an analog of the endocannabinoid AEA found in brain tissue and in chocolate. It is one of the long chain fatty acid ethanolamides that accumulates rapidly in infarcted tissue, but its biosynthesis is reduced in the intestine of rats following food deprivation. OEA is an endogenous, potent agonist for PPARα, exhibiting an EC50 value of 120 nM in a transactivation assay. Systemic administration of OEA suppresses food intake and reduces weight gain in rats (10 mg/kg intraperitoneally) and PPARα wild-type mice, but not in PPARα knockout mice. These data indicate that OEA regulates food intake by a PPARα-mediated mechanism.

UsesN-Oleoyl Ethanolamide is an agonist of peroxisome proliferator-activated receptor-α (PPAR-α). N-Oleoyl Ethanolamide generates an intestinal signal that stimulates central dopamine activity establishing a link between caloric-homeostatic and hedonic-homeostatic controllers. Oleoyl Ethanolamide has been implicated as the molecular mechanism associated with gastric bypass success. N-Oleoyl Ethanolamide is a selective GPR55 agonist.

General DescriptionOleoylethanolamide (OEA) is an endogenous fatty acid ethanolamine. Small intestine cells, adipose tissues, neurons and astrocytes produces OEA.

Upstream & downstream products

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
山东天微医药科技有限公司+86-18653895227 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海毕合生物化学技术有限公司13816464724 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Oleoyl ethanolamide is an N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide. It has a role as a PPARalpha agonist, an EC 3.5.1.23 (ceramidase) inhibitor and a geroprotector. It is a N-(long-chain-acyl)ethanolamine, an endocannabinoid and a N-acylethanolamine 18:1. It is functionally related to an oleic acid.

Related reactions

5 records
New reaction record

Compound notes

Loading…