Phenylacetic acid
Encyclopedia
Phenylacetic acid is an organic compound
containing a phenyl functional group
and a carboxylic acid
functional group. It is a white solid with a disagreeable odor
. Because it is used in the illicit production of phenylacetone
(used in the manufacture of meth
/amphetamine
s), it is subject to controls
in the United States
.
(a type of plant hormone
), found predominantly in fruit
s. However, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid
. It is also the oxidation product of phenethylamine
when acted on by the enzyme monoamine oxidase
found in humans and many other organisms.
:
s, possessing a honey-like odour in low concentration
s, and is also used in penicillin G
production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine
. This compound is then secreted by the patient's body.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
containing a phenyl functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
and a carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...
functional group. It is a white solid with a disagreeable odor
Odor
An odor or odour is caused by one or more volatilized chemical compounds, generally at a very low concentration, that humans or other animals perceive by the sense of olfaction. Odors are also commonly called scents, which can refer to both pleasant and unpleasant odors...
. Because it is used in the illicit production of phenylacetone
Phenylacetone
Phenylacetone , is an organic compound. It is a clear oil with a refractive index of 1.5168. This substance is used in the manufacture of methamphetamine and amphetamine as a starting material or intermediate, where it is commonly known as P2P...
(used in the manufacture of meth
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
/amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
s), it is subject to controls
Chemical Diversion and Trafficking Act
The Chemical Diversion and Trafficking Act of 1988 was an amendment to the Controlled Substances Act to regulate precursor chemicals, essential chemicals, tableting machines, and encapsulating machines by imposing record keeping and import/export reporting requirements on transactions involving...
in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
.
Occurrence
Phenylacetic acid has been found to be an active auxinAuxin
Auxins are a class of plant hormones with some morphogen-like characteristics. Auxins have a cardinal role in coordination of many growth and behavioral processes in the plant's life cycle and are essential for plant body development. Auxins and their role in plant growth were first described by...
(a type of plant hormone
Plant hormone
Plant hormones are chemicals that regulate plant growth, which, in the UK, are termed 'plant growth substances'. Plant hormones are signal molecules produced within the plant, and occur in extremely low concentrations. Hormones regulate cellular processes in targeted cells locally and, when moved...
), found predominantly in fruit
Fruit
In broad terms, a fruit is a structure of a plant that contains its seeds.The term has different meanings dependent on context. In non-technical usage, such as food preparation, fruit normally means the fleshy seed-associated structures of certain plants that are sweet and edible in the raw state,...
s. However, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid
Indole-3-acetic acid
Indole-3-acetic acid, also known as IAA, is a heterocyclic compound that is a phytohormone called auxin. This colourless solid is native plant compound, potent and the most important auxin...
. It is also the oxidation product of phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
when acted on by the enzyme monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
found in humans and many other organisms.
Preparation
This compound may be prepared by the hydrolysis of benzyl cyanideBenzyl cyanide
Benzyl cyanide is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is a precursor to several derivatives.-Synthesis, reactions, and applications:...
:
Applications
Phenylacetic acid is used in some perfumePerfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...
s, possessing a honey-like odour in low concentration
Concentration
In chemistry, concentration is defined as the abundance of a constituent divided by the total volume of a mixture. Four types can be distinguished: mass concentration, molar concentration, number concentration, and volume concentration...
s, and is also used in penicillin G
Penicillin
Penicillin is a group of antibiotics derived from Penicillium fungi. They include penicillin G, procaine penicillin, benzathine penicillin, and penicillin V....
production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine
Phenylacetylglutamine
Phenylacetylglutamine is a product formed by the conjugation of phenylacetate and glutamine. It is a common metabolite that can be found in human urine....
. This compound is then secreted by the patient's body.