[2,3-bis(octadec-9-enoyloxy)propyl]trimethylazanium methyl sulfate

• ChemBase ID: 156126
• Molecular Formular: C43H83NO8S
• Molecular Mass: 774.18602
• Monoisotopic Mass: 773.58393962
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)OCC(C[N+](C)(C)C)OC(=O)CCCCCCC/C=C/CCCCCCCC.COS(=O)(=O)[O-]
• Canonical SMILES: COS(=O)(=O)[O-].CCCCCCCC/C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C/CCCCCCCC)C[N+](C)(C)C
• InChI: InChI=1S/C42H80NO4.CH4O4S/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-41(44)46-39-40(38-43(3,4)5)47-42(45)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2;1-5-6(2,3)4/h20-23,40H,6-19,24-39H2,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
• InChIKey: RSMRWWHFJMENJH-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [2,3-bis(octadec-9-enoyloxy)propyl]trimethylazanium methyl sulfate
• IUPAC Traditional name: [2,3-bis(octadec-9-enoyloxy)propyl]trimethylazanium methyl sulfate(1-)
• Synonyms: N-(2,3-Dioleoyloxy-1-propyl)trimethylammonium methyl sulfate; Transfection reagent; DOTAP methosulfate

Database IDs

• CAS Number: 144189-73-1
• MDL Number: MFCD00274414
• PubChem SID: 24889327; 162250264
• PubChem CID: 22996898

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 9.603935
• LogD (pH = 7.4): 9.603935
• Log P: 9.603935
• Molar Refractivity: 215.9765 cm^3
• Polarizability: 80.64132 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Grade: for molecular biology
• Empirical Formula (Hill Notation): C43H83NO8S

DETAILS

Sigma Aldrich - 90189

Application
Cationic liposome-forming compound for transfection of DNA, RNA and other negatively charged molecules into eukaryotic cells. Mixing DOTAP with DNA results in spontaneously formed stable complexes that can be directly added to cell culture medium. These complexes fuse with the cell membrane and release DNA into the cytoplasm. The cells are transfected efficiently without cytotoxic effects. Use approximately 5-10 μg DOTAP per μg DNA and approximately 10-20 μg DOTAP per mL cell culture medium. The optimal working concentration and transfection time depends in part on the cell line used, and the type of material (RNA, DNA, protein) loaded.
liposomal transfection reagent (1mg/ml)
Other Notes
Mediates transfection of mammalian cells1