1,2-Dioleoyl-3-trimethylammonium propane (often abbreviated DOTAP or 18:1TAP) is a di-chain, or gemini, cationic surfactant. It is most commonly encountered as an active ingredient in certain fabric softeners. The pure material can also be used for the liposomal-

transfection Transfection is the process of deliberately introducing naked or purified nucleic acids into eukaryotic cells. It may also refer to other methods and cell types, although other terms are often preferred: "transformation" is typically used to desc ...

of DNA, RNA and other negatively charged molecules.

Synthesis

The commercial material used for fabric softening is formed by the di- esterification of 2,3-epoxypropyltrimethylammoniumchloride (EPTAC) with partially hydrogenated

palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of the oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 33% of global oils produced from ...

and as such contains a mixture of

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

tails;

palmitic Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Li ...

(saturated C16),

stearic Stearic acid ( , ) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "''stéar''", which means tallow. ...

(saturated C18),

oleic Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega ...

(monounsaturated C18) and linoleic (polyunsaturated C18). In practice the saturated di-sterate compound tend to be the major component of these mixtures. DiesterCl

Material intended for transfection is prepared similarly from high purity oleic acid.

Applications

Fabric softener

It was originally introduced into European markets during the 1990s due to concerns over the environmental effects of DODAC, which was the principle softener used at the time. The main difference was the incorporation of cleavable ester groups intended to accelerate its biodegradation. It is a superior softener to di- and

triethanolamine Triethanolamine, or TEA is a viscous organic compound that is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples m ...

based softeners but suffers from an increased tendency to hydrolyse. Small patch test studies have not shown any clear evidence of it acting is a skin irritant.

Liposomal transfection agent

DOTAP is a cationic surfactant and is able to form stable

cationic liposome Cationic liposomes are spherical structures that contain positively charged lipids. Cationic liposomes can vary in size between 40 nm and 500 nm, and they can either have one lipid bilayer (monolamellar) or multiple lipid bilayers (multila ...

s in solution, these readily absorb DNA and other negatively charged organic compounds. The DNA laden liposomes can then be added directly to cell culture medium, where they will combine with the cell membrane and release their payload into the cell.

References

{{Reflist Quaternary ammonium compounds Cationic surfactants Laundry substances