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 ...
CH
3(CH
2)
7CO
2H. 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 solvent
A solvent (s) (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 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
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...
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
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 are ...
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
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond ...
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. ]
:
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 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 applicatio ...
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
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 organic co ...
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
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 ...
.
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.
Plasticiz ...
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 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 spray
Pepper spray, oleoresin capsicum spray, OC spray, capsaicin spray, or capsicum spray is a lachrymatory agent (a compound that irritates the eyes to cause a burning sensation, pain, and temporary blindness) used in policing, riot control, cr ...
s. The
ammonium salt
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...
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
Glyphosate (IUPAC name: ''N''-(phosphonomethyl)glycine) is a broad-spectrum Herbicide, systemic herbicide and Crop desiccation, crop desiccant. It is an organophosphorus compound, specifically a phosphonate, which acts by inhibiting the plan ...
, a non-selective herbicide, for a quick burn-down effect in the control of weeds in
turfgrass
A lawn is an area of soil-covered land planted with grasses and other durable plants such as clover which are maintained at a short height with a lawnmower (or sometimes grazing animals) and used for aesthetic and recreational purposes. L ...
.
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 car ...
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 is the edible berry of the plant ''Solanum lycopersicum'', commonly known as the tomato plant. The species originated in western South America, Mexico, and Central America. The Mexican Nahuatl word gave rise to the Spanish word ...
'', and the methyl against ''
Heterodera glycines
The soybean cyst nematode (SCN), ''Heterodera glycines'', is the most devastating pest to soybean crop yields in the U.S., targeting the roots of soybean and other legume plants. When infection is severe SCNs cause stunting, yellowing, impaired c ...
'' and ''
M. incognita'' on ''
Glycine max
Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogeni ...
''.
[ p.229.]
Esters of pelargonic acid are precursors to lubricants.
Pharmacological effects
Pelargonic acid may be more potent than
valproic acid
Valproate (VPA) and its valproic acid, 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 ...
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
Teratology is the study of abnormalities of physiological development in organisms during their life span. It is a sub-discipline in medical genetics which focuses on the classification of congenital abnormalities in dysmorphology. The related t ...
.
See also
*
List of saturated fatty acids
See also
*List of unsaturated fatty acids
*Carboxylic acid
**List of carboxylic acids
*Dicarboxylic acid
{{DEFAULTSORT:List Of Saturated Fatty Acids
Saturated Fatty Acids
A saturated fat is a type of fat in which the fatty acid chains ...
*
List of carboxylic acids
Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature, which ensures systematic and consistent naming of chemicals. Numerous organic compounds have o ...
References
External links
MSDS at affymetrix.com
{{Authority control
Alkanoic acids
Herbicides
Nematicides