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

• ChemBase ID: 132531
• 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/b22-20-,23-21-
• InChIKey: RSMRWWHFJMENJH-LQDDAWAPSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: {2,3-bis[(9Z)-octadec-9-enoyloxy]propyl}trimethylazanium methyl sulfate
• IUPAC Traditional name: {2,3-bis[(9Z)-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: 162226808; 24893370
• PubChem CID: 16218742

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

Physical Property

• Apperance: clear to hazy colorless to faint yellow buffered aqueous suspension

Safety Information

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

Product Information

• Concentration: 1 mg/mL

DETAILS

Sigma Aldrich - D1163

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.
Features and Benefits

• Compatible with both serum and serum-free transfection protocols
• 5-100 times more efficient than calcium phosphate- or DEAE-dextran-based transfection
• Low cytotoxicity results in increased transformation efficiency.
• Compatible for use with in vivo transfection applications
• Packaged to prevent oxidation and peroxide formation, eliminating damage to transfection molecules and cells
Physical form
Suspension in MES-buffered saline, pH 6.2