(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

• ChemBase ID: 129042
• Molecular Formular: C42H82NO8P
• Molecular Mass: 760.076141
• Monoisotopic Mass: 759.57780522
• SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C/CCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=C/CCCCCCCC)COP(=O)(OCC[N+](C)(C)C)[O-]
• InChI: InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/t40-/m1/s1
• InChIKey: WTJKGGKOPKCXLL-RRHRGVEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium; (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9E)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• IUPAC Traditional name: (2-{[(2R)-3-(hexadecanoyloxy)-2-(octadec-9-enoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium; (2-{[(2R)-3-(hexadecanoyloxy)-2-[(9E)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
• Synonyms: 1-Palmitoyl-2-oleoylphosphatidylcholine; POPC; (7R,17Z)-4-Hydroxy-N,N,N-trimethyl-9-oxo-7-[[(1-oxohexadecyl)oxy]methyl]-3,5,8-trioxa-4-phosphahexacos-17-en-1-aminium 4-oxide, inner salt; 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine; 1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine; 1-Hexadecanoyl-2-(cis-9-octadecenoyl)-sn-glycero-3-phosphocholine; 3-sn-Phosphatidylcholine, 2-oleoyl-1-palmitoyl; L-β-Oleoyl-γ-palmitoyl-α-lecithin; PC(16:0/18:1(9Z)); PC(16:0/18:1); PC(16:0/18:1w9); POPC; 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine

Database IDs

• CAS Number: 26853-31-6
• EC Number: 248-056-7
• MDL Number: MFCD00043212
• Beilstein Number: 4173237
• PubChem SID: 24898382; 162223343
• PubChem CID: 6506401; 5497103
• Chemspider ID: 4593686
• Wikipedia Title: POPC

CALCULATED PROPERTIES

• Acid pKa: 1.8550572
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.6645155
• LogD (pH = 7.4): 10.664612
• Log P: 8.641012
• Molar Refractivity: 226.1837 cm^3
• Polarizability: 85.82576 Å^3
• Polar Surface Area: 111.19 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.5% (GC); ≥98% (TLC); ≥99.0% (TLC)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C42H82NO8P

DETAILS

Sigma Aldrich - 42773

General description
Non-pyrogenic, well-defined liposomes, loaded with a molecule of choice, are formed by a single hydration step.
Application
The effect of non-ionic detergent on liposomes was studied with giant POPC liposomes. Increasing concentrations of detergent cause tubular protrusions, then indentations, to develop on spherical liposomes. At higher detergent concentrations, the liposomes burst.1

Sigma Aldrich - P3017

General description
Non-pyrogenic, well-defined liposomes, loaded with a molecule of choice, are formed by a single hydration step.
Application
The effect of non-ionic detergent on liposomes was studied with giant POPC liposomes. Increasing concentrations of detergent cause tubular protrusions, then indentations, to develop on spherical liposomes. At higher detergent concentrations, the liposomes burst.1