N-(2-hydroxyethyl)octadec-9-enamide

• ChemBase ID: 110820
• Molecular Formular: C20H39NO2
• Molecular Mass: 325.52916
• Monoisotopic Mass: 325.29807949
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCO
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)NCCO
• InChI: 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)
• InChIKey: BOWVQLFMWHZBEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-hydroxyethyl)octadec-9-enamide
• IUPAC Traditional name: N-(2-hydroxyethyl)octadec-9-enamide
• Synonyms: OLEIC MONOETHANOLAMIDE; Oleoylethanolamide; N-(Hydroxyethyl)oleamide; N-(cis-9-Octadecenoyl)ethanolamine; OEA; oleoylethanolamide; N-Oleoylethanolamine

Database IDs

• CAS Number: 111-58-0
• EC Number: 203-884-8
• MDL Number: MFCD00045972
• PubChem SID: 24278603; 162096479
• PubChem CID: 5353809; 5283454
• Wikipedia Title: Oleoylethanolamide

CALCULATED PROPERTIES

• Acid pKa: 15.469626
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.5104294
• LogD (pH = 7.4): 5.51043
• Log P: 5.51043
• Molar Refractivity: 100.4134 cm^3
• Polarizability: 39.165314 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: soluble in ethanol and DMSO
• Apperance: White solid
• Melting Point: 59-60°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CNR1(1268), CNR2(1269), PPARA(5465), TRPV1(7442)mouse ... Cnr2(12802)rat ... Cnr1(25248)

Product Information

• Purity: ~98% (TLC)
• Empirical Formula (Hill Notation): C20H39NO2

DETAILS

Sigma Aldrich - O0383

Biochem/physiol Actions
Peroxisome proliferator-activator receptor α (PPARα) agonist