Pelargonic acid, also called nonanoic acid, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with

structural formula The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are connected to one another. The chemical bonding within the molecule is al ...

. It is a nine-carbon

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in

organic solvent A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s. The

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s and

salts In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions ( cations) and negatively charged ions (anions), which results in a compound with no net electric charge (electrically neutral). ...

of pelargonic acid are called pelargonates or nonanoates. The acid is named after the

pelargonium ''Pelargonium'' () is a genus of flowering plants that includes about 280 species of perennial plant, perennials, succulent plant, succulents, and shrubs, common name, commonly called geraniums, pelargoniums, or storksbills. ''Geranium'' is also ...

plant, since oil from its leaves contains

esters In chemistry, an ester is a chemical compound, compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds c ...

of the acid.

Preparation

Together with

azelaic acid Azelaic acid (AzA), or nonanedioic acid, is an organic compound with the formula HOOC(CH2)7carboxylic acid, COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse ind ...

, it is produced industrially by

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the Saturated and unsaturated compounds, unsaturated bonds are Bond cleavage, cleaved with ozone (). Multiple carbon–carbon bond are replaced by carbonyl () groups, such as aldehydes ...

oleic acid 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 due to the presence of impurities. In chemical terms, oleic acid is cl ...

. : Alternatively, pelargonic acid can be produced in a two-step process beginning with coupled

dimerization In chemistry, dimerization is the process of joining two identical or similar molecular entities by bonds. The resulting bonds can be either strong or weak. Many symmetrical chemical species are described as dimers, even when the monomer is u ...

and

hydroesterification In industrial chemistry, carboalkoxylation is a process for converting alkenes to esters. This reaction is a form of carbonylation. A closely related reaction is hydrocarboxylation, which employs water in place of alcohols. A commercial applicat ...

of 1,3-

butadiene 1,3-Butadiene () is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two ...

. This step produces a doubly unsaturated C9-ester, which can be

hydrogenated Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organi ...

to give esters of pelargonic acid. : : A laboratory preparation involves permanganate oxidation of

1-decene Decene is an organic compound with the chemical formula . Decene contains a chain of ten carbon atoms with one double bond, making it an alkene. There are many isomers of decene depending on the position and geometry of the double bond. Dec-1- ...

Occurrence and uses

Pelargonic acid occurs naturally as esters in the oil of ''

Pelargonium ''Pelargonium'' () is a genus of flowering plants that includes about 280 species of perennial plant, perennials, succulent plant, succulents, and shrubs, common name, commonly called geraniums, pelargoniums, or storksbills. ''Geranium'' is also ...

''. Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizer ...

s and

lacquer Lacquer is a type of hard and usually shiny coating or finish applied to materials such as wood or metal. It is most often made from resin extracted from trees and waxes and has been in use since antiquity. Asian lacquerware, which may be c ...

s. The derivative 4-nonanoylmorpholine is an ingredient in some

pepper spray Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, mace, or capsicum spray is a Tear gas, lachrymator (tear gas) product containing as its active ingredient the chemical compound capsaicin, which irritates the eyes with burning ...

s. The

ammonium salt Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) molecular ion with the chemical formula or . It is formed by the addition of a proton (a hydrogen nucleus) to ammonia (). Ammonium i ...

of pelargonic acid, ammonium pelargonate, is a

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

. It is commonly used in conjunction with

glyphosate Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum systemic herbicide and crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by EPSP inhibitor, inhibiting the plant enzyme 5-en ...

, a non-selective herbicide, for a quick burn-down effect in the control of weeds in

turfgrass Sod is the upper layer of turf that is harvested for transplanting. Turf consists of a variable thickness of a soil medium that supports a community of turfgrasses. In British and Australian English, sod is more commonly known as ''turf'', ...

. It works by causing leaks in plant cell membranes, allowing chlorophyll molecules to escape the chloroplast. Under sunlight, these misplaced molecules cause immense oxidative damage to the plant. The methyl form and ethylene glycol pelargonate act as

nematicide A nematicide is a type of chemical pesticide used to kill plant- parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a ...

s against ''

Meloidogyne javanica ''Meloidogyne javanica'' is a species of plant-pathogenic nematodes. It is one of the tropical root-knot nematodes and a major agricultural pest in many countries. It has many hosts. ''Meloidogyne javanica'' reproduces by obligatory mitotic part ...

'' on ''

Solanum lycopersicum The tomato (, ), ''Solanum lycopersicum'', is a plant whose fruit is an edible berry that is eaten as a vegetable. The tomato is a member of the nightshade family that includes tobacco, potato, and chili peppers. It originated from and was d ...

'', and the methyl against '' Heterodera glycines'' and '' M. incognita'' on ''

Glycine max The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source of f ...

''. p.229. Esters of pelargonic acid are precursors to lubricants.

Pharmacological effects

Pelargonic acid may be more potent than

valproic acid Valproate (valproic acid, VPA, sodium valproate, and valproate semisodium forms) are medications primarily used to treat epilepsy and bipolar disorder and prevent migraine headaches. They are useful for the prevention of seizures in those with ...

in treating seizures. Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on HDAC inhibition, suggesting that it is unlikely to show HDAC inhibition-related teratogenicity.

References

External links

MSDS at affymetrix.com
{{Authority control Alkanoic acids Herbicides Nematicides

Preparation

Occurrence and uses

Pharmacological effects

See also

References

External links