1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate

• ChemBase ID: 125253
• Molecular Formular: C23H38O4
• Molecular Mass: 378.54542
• Monoisotopic Mass: 378.2770097
• SMILES: O=C(OC(CO)CO)CCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)OC(CO)CO
• InChI: InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3
• InChIKey: RCRCTBLIHCHWDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate
• IUPAC Traditional name: 1,3-dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate
• Synonyms: 2-Arachidonoylglycerol; 2-AG; 2-arachidonoylglycerol; 2-Arachidonyl glycerol

Database IDs

• CAS Number: 53847-30-6
• EC Number: 200-835-2
• MDL Number: MFCD01862600
• PubChem SID: 24891388; 162219603
• PubChem CID: 5353310; 5282280
• CHEBI ID: 52392
• CHEMBL: 122972
• Chemspider ID: 4445451
• IUPHAR ligand ID: 729
• Wikipedia Title: 2-Arachidonoylglycerol

CALCULATED PROPERTIES

• Acid pKa: 14.278373
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.4126277
• LogD (pH = 7.4): 5.4126277
• Log P: 5.4126277
• Molar Refractivity: 116.9779 cm^3
• Polarizability: 44.134323 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: acetonitrile solution
• Flash Point: 2 °C; 35.6 °F

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• UN Number: 1648
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302 + H332-H319
• GHS Precautionary statements: P210-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1648 3/PG 2
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... FAAH(2166)rat ... Cnr1(25248), Cnr2(57302)

Product Information

• Purity: ≥98% (HPLC)
• Concentration: ~10 mg/mL
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C23H38O4

DETAILS

Sigma Aldrich - A8973

Biochem/physiol Actions
Endogenous cannabinoid receptor agonist.
Caution
Air sensitive