(2-{[(2R)-2-[(8-carboxyoctanoyl)oxy]-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 153751
• Molecular Formular: C33H66NO9P
• Molecular Mass: 651.852201
• Monoisotopic Mass: 651.44751933
• SMILES: CCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCC(=O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCOC[C@@H](OC(=O)CCCCCCCC(=O)O)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C33H66NO9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-23-27-40-29-31(30-42-44(38,39)41-28-26-34(2,3)4)43-33(37)25-22-19-17-18-21-24-32(35)36/h31H,5-30H2,1-4H3,(H-,35,36,38,39)/t31-/m1/s1
• InChIKey: ZDFOCDTXDPKJKA-WJOKGBTCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-2-[(8-carboxyoctanoyl)oxy]-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-2-[(8-carboxyoctanoyl)oxy]-3-(hexadecyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1-O-Hexadecyl-2-O-(9-carboxyoctanoyl)-sn-glyceryl-3-phosphocholine; 1-O-Hexadecyl-2-azelaoyl-sn-glycero-3-phosphocholine; hexadecyl azelaoyl phosphatidylcholine; Azelaoyl PAF

Database IDs

• EC Number: 200-578-6
• MDL Number: MFCD03412018
• PubChem SID: 162247890
• PubChem CID: 17757205

CALCULATED PROPERTIES

• Acid pKa: 1.8539555
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 4.9989376
• LogD (pH = 7.4): 3.2170694
• Log P: 4.0623693
• Molar Refractivity: 185.5689 cm^3
• Polarizability: 69.98275 Å^3
• Polar Surface Area: 131.42 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: liquid
• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 7-16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Product Information

• Concentration: 10 mg/mL in ethanol
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C33H66NO9P

DETAILS

Sigma Aldrich - A6850

Biochem/physiol Actions
Potent PPARγ agonist.
Application
Azelaoyl PAF is a potent PPARγ agonist. Azelaoyl PAF has been used to investigate whether peroxisome proliferator-activated receptors gamma agonists could play a role in the treatment of Friedreich′s ataxia, a neurodegenerative disease due to frataxin deficiency.