Pelargonic acid, also called nonanoic acid, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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 possibly arranged in the real three-dimensional space. The chemical bondi ...

CH₃(CH₂)₇CO₂H. It is a nine-carbon

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 ...

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

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s and salts 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 perennials, succulents, and shrubs, commonly called geraniums, pelargoniums, or storksbills. '' Geranium'' is also the botanical name and common name of a separ ...

plant, since oil from its leaves contains esters of the acid.

Preparation

Together with

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

, it is produced industrially by ozonolysis of

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. In chemical terms, oleic acid is classified as a monounsaturated omega ...

.David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2006, Wiley-VCH, Weinheim. :

\ce \longrightarrow  + \ce

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

dimerization A dimer () (''wikt:di-, di-'', "two" + ''-mer'', "parts") is an oligomer consisting of two monomers joined by bonds that can be either strong or weak, Covalent bond, covalent or Intermolecular force, intermolecular. Dimers also have significant im ...

and hydroesterification of 1,3-

butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. 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 viny ...

. This step produces a doubly unsaturated C9-ester, which can be hydrogenated to give esters of pelargonic acid. :\overset + CO + CH3OH -> CH2=CH(CH2)3CH=CHCH2CO2CH3 :CH2=CH(CH2)3CH=CHCH2CO2CH3 + 2 H2 -> \underset 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

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

s. The derivative

4-nonanoylmorpholine 4-Nonanoylmorpholine ''pelargonic acid morpholide, N-nonanoylmorpholine, MPK or МПК (for russian: морфолид пеларгоновой кислоты), or MPAis an amide of pelargonic acid and morpholine. Properties 4-Nonanoylmorpholine ...

is an ingredient in some pepper sprays. The ammonium salt of pelargonic acid,

ammonium pelargonate Ammonium nonanoate is a nonsystemic, broad-spectrum contact herbicide that has no soil activity. It can be used for the suppression and control of weeds, including grasses, vines, underbrush, and annual/perennial plants, including moss, saplings ...

, is a

herbicide Herbicides (, ), also commonly known as weedkillers, 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 fo ...

. It is commonly used in conjunction with glyphosate, a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass. The methyl form and ethylene glycol pelargonate act as nematicides against '' Meloidogyne javanica'' on '' Solanum lycopersicum'', and the methyl against '' Heterodera glycines'' and '' M. incognita'' on '' Glycine max''. p.229. Esters of pelargonic acid are precursors to lubricants.

Pharmacological effects

Pelargonic acid may be more potent than valproic acid in treating seizures. Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on

HDAC inhibition Histone deacetylase inhibitors (HDAC inhibitors, HDACi, HDIs) are chemical compounds that inhibit histone deacetylases. HDIs have a long history of use in psychiatry and neurology as mood stabilizers and anti-epileptics. More recently they are be ...

, 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