Dioleoyl-3-trimethylammonium Propane
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Dioleoyl-3-trimethylammonium Propane
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 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 and as such contains a mixture of fatty acid tails; palmitic (saturated C16), stearic (saturated C18), oleic (monounsaturated C18) and linoleic (polyunsaturated C18). In practice the saturated di-sterate compound tend to be the major component of these mixtures. 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 e ...
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Methane Sulfonate
In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (). In salts, the mesylate is present as the anion. When modifying the international nonproprietary name of a pharmaceutical substance containing the group or anion, the spelling used is sometimes mesilate (as in ''imatinib mesilate'', the mesylate salt of imatinib). Mesylate esters are a group of organic compounds that share a common functional group with the general structure , abbreviated , where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions. Preparation Mesylates are generally prepared by treating an alcohol and methanesulfonyl chloride in the presence of a base, such as triethylamine. Mesyl Related to mesylate is the mesyl (Ms) or methanesulfonyl (CH3SO2) functional group. Methanesulfonyl chloride is often referred to as mesyl chloride. Whereas mesylates are often hydrolytically labile, mesyl groups, when attached to nitro ...
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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-9 fatty acid, abbreviated with a lipid number of 18:1 ''cis''-9, and a main product of Δ9 desaturase. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The name derives from the Latin word ''oleum'', which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. Occurrence Fatty acids (or their salts) often do not occur as such in biological systems. Instead fatty acids such as oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. Oleic acid is the most common monounsaturated fatty acid in nature. It is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters. Triglycerides of oleic ...
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Quaternary Ammonium Compounds
In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds (called quaternary amines in oilfield parlance) are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule. Quats are used in consumer applications including as antimicrobials (such as detergents and disinfectants), fabric softeners, and hair conditioners. As an antimicrobial, they are able to inactivate enveloped viruses (such as SARS-CoV-2). Quats tend to be gentler on surfaces than bleach-based disinfectants, and are generally fabric-safe. Synthesis Quaternary ammonium compou ...
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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 (multilamellar). The positive charge of the phospholipids allows cationic liposomes to form complexes with negatively charged nucleic acids ( DNA, mRNA, and siRNA) through ionic interactions. Upon interacting with nucleic acids, cationic liposomes form clusters of aggregated vesicles. These interactions allow cationic liposomes to condense and encapsulate various therapeutic and diagnostic agents in their aqueous compartment or in their lipid bilayer. These cationic liposome-nucleic acid complexes are also referred to as lipoplexes. Due to the overall positive charge of cationic liposomes, they interact with negatively charged cell membranes more readily than classic liposomes. This positive charge can also create some issues ''in vivo'', such as ...
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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 may appear yellow because of impurities. Production Triethanolamine is produced from the reaction of ethylene oxide with aqueous ammonia, also produced are ethanolamine and diethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants. : Applications Triethanolamine is used primarily in making surfactants, such as for emulsifier. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes fatty acids, adjusts and pH buffer, buffers the pH, and solubilizes oils and other ingredients that are not completely Solubility, soluble in water. Triethanolammonium salts in some cases are more soluble than salts of alkali metals that might be us ...
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Dimethyldioctadecylammonium Chloride
Dimethyldioctadecylammonium chloride also commonly distearyl dimethyl ammonium chloride is an organic compound classified as quaternary ammonium salt. The nitrogen center substituted with two methyl groups and two stearyl groups. The combination of long-chain hydrocarbon groups and the cationic ammonium confers surfactant- or a detergent-like properties. For professional use only, it can be found in many wares-and-equipment sanitizers as well as cleaner/sanitizer combinations that are standard in the foodservice industry – it was once a major component of fabric softeners, but has been largely phased out because of its low biodegradability. In household products, it may also be found as an ingredient in cosmetics and hair conditioners in which it is added primarily for its antistatic effects. It is also used in organic synthesis as a phase transfer catalyst to increase reaction rates in a two-phase organic-water system. See also * Dimethyldioctadecylammonium bromide – ...
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Linoleic
Linoleic acid (LA) is an organic compound with the formula COOH(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are ''cis''. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 ''cis''-9,12. A linoleate is a salt or ester of this acid. Linoleic acid is a polyunsaturated omega-6 fatty acid. It is a colorless liquid that is virtually insoluble in water but soluble in many organic solvents. It typically occurs in nature as a triglyceride (ester of glycerin) rather than as a free fatty acid. It is one of two essential fatty acids for humans, who must obtain it through their diet, and the most essential, because the body uses it as a base to make the others. The word "linoleic" derives from the Latin ''linum'' "flax" + ''oleum'' "oil", reflecting the fact that it was first isolated from linseed oil. History In 1844, F. Sacc, working at the laboratory of Justus von Liebig, isolated linoleic acid from linseed oil. In 1886, K. Peters determined the existence of two double bo ...
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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. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid.Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra "The Lipid Handbook with Cd-Rom. 3rd ed. Boca Raton: CRC Press, 2007. , The triglyceride derived from three molecules of stearic acid is called stearin. Occurrence and production Stearic acid is more abundant in animal fat (up to 30%) than in vegetable fat (typically <5%). The important exceptions are the foods (34%) and
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Cationic Surfactant
Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants. The word "surfactant" is a blend of ''surface-active agent'', coined . Agents that increase surface tension are "surface active" in the literal sense but are not called surfactants as their effect is opposite to the common meaning. A common example of surface tension increase is salting out: by adding an inorganic salt to an aqueous solution of a weakly polar substance, the substance will precipitate. The substance may itself be a surfactant – this is one of the reasons why many surfactants are ineffective in sea water. Composition and structure Surfactants are usually organic compounds that are amphiphilic, meaning each molecule contains both a hydrophilic "water-seeking" group (the ''head''), and a hydrop ...
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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 Lipid Handbook, 3rd ed. Boca Raton: CRC Press, 2007. , Its chemical formula is CH3(CH2)14COOH, and its C:D (the total number of carbon atoms to the number of carbon-carbon double-bonds) is 16:0. It is a major component of the oil from the fruit of oil palms (palm oil), making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4). Occurrence and production Palmitic acid was discovered by Edmond Frémy in 1840, in saponified palm oil. This remains the primary industrial route for its production, with the triglycerides (fat ...
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