(2-aminoethoxy)[(2S)-3-(hexadecanoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid

• ChemBase ID: 153666
• Molecular Formular: C39H74NO8P
• Molecular Mass: 715.980521
• Monoisotopic Mass: 715.51520496
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](COP(=O)(O)OCCN)OC(=O)CCCCCCC/C=C/C/C=C/CCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](OC(=O)CCCCCCC/C=C/C/C=C/CCCCC)COP(=O)(OCCN)O
• InChI: InChI=1S/C39H74NO8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-39(42)48-37(36-47-49(43,44)46-34-33-40)35-45-38(41)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,37H,3-10,12,14-16,19-36,40H2,1-2H3,(H,43,44)/t37-/m0/s1
• InChIKey: HBZNVZIRJWODIB-QNGWXLTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-aminoethoxy)[(2S)-3-(hexadecanoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid
• IUPAC Traditional name: 2-aminoethoxy(2S)-3-(hexadecanoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxyphosphinic acid
• Synonyms: 3-sn-Phosphatidylethanolamine, 2-linoleoyl-1-palmitoyl; L-α-Phosphatidylethanolamine, β-linoleoyl-γ-palmitoyl; 2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine

Database IDs

• CAS Number: 13206-00-3
• MDL Number: MFCD00058604
• Beilstein Number: 2033925
• PubChem SID: 162247805
• PubChem CID: 71311714

CALCULATED PROPERTIES

• Acid pKa: 1.8688003
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 10.616169
• LogD (pH = 7.4): 10.615238
• Log P: 10.616209
• Molar Refractivity: 202.4391 cm^3
• Polarizability: 80.233826 Å^3
• Polar Surface Area: 134.38 Å^2
• Rotatable Bonds: 39
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 1888
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 45-46-22-38-48/20/22
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H350-H373
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1888 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (10 mg phospholipid per ml CHCl3, TLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C39H74NO8P

DETAILS

Sigma Aldrich - 62225

Application
2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine is the substrate for human group V phospholipase A2 1. In addition, 2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine provides an in vitro model for studying and a diagnosis tool for diagnosis of oxidative stress 2.