Oleoylethanolamide
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Grundinformationen
- CAS
111-58-0- Standard-SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCO- InChIKey
BOWVQLFMWHZBEF-KTKRTIGZSA-N- Summenformel
- C20H39NO2
- Durchschnittliche Molmasse
- 325,5 g/mol
- Monoisotopische Masse
- 325,29807949
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Oleoylethanolamide
- IUPAC
- (Z)-N-(2-hydroxyethyl)octadec-9-enamide
Namen und Synonyme
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
Weitere Namen anzeigen
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-CHEBI:71466RefChem:856533DTXCID9024516203-884-8Oleoylethanolaminen-oleoylethanolamineOleylethanolamide
Datenbank-Bezeichner
- CAS
111-58-0- PubChem CID
- 5283454
- ChEMBL
CHEMBL280065- ChEBI
CHEBI:71466- UNII
- 1HI5J9N8E6
- EC Number
- 203-884-8、921-073-3
- Nikkaji
- J193.596H
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 6,3
- Polarare Oberfläche (TPSA)
- 49,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 17
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 277
Experimentelle und physikochemische Eigenschaften
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl ethanolamines (endocannabinoids) [FA0804]
Cosmetics
Cosmetic ingredients (Oleamide MEA) -> CIR (Cosmetic Ingredient Review)
Antistatic; Viscosity controlling; Foam boosting
Personal care product
Physical Description
Other Solid
Solid
Collision Cross Section192.94 Ų [M+H]+ [CCS Type: TIMS; Method: single field calibrated]
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Regulatory Information
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)
REACH registered substance: N-(2-hydroxyethyl)oleamide (EC: 203-884-8)
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%)
Toxikologische Informationen
Toxicity Summary
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...
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
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
Verwendung und Herstellung
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
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
9-Octadecenamide, N-(2-hydroxyethyl)-, (9Z)-: ACTIVE
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