Decarboxylation

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Decarboxylation

Decarboxylation is any chemical reaction

Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide

Carbon dioxide

Biosynthesis

Biosynthesis is a phenomenon wherein chemical compounds are produced from simpler reagents. Biosynthesis, unlike chemosynthesis, takes place within living organisms and is generally catalyst by enzymes....
decarboxylations of amino acid

Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s to amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s are:

Other decarboxylation reactions from the citric acid cycle

Citric acid cycle

The citric acid cycle ? also known as the tricarboxylic acid cycle ; the Krebs cycle; or, more rarely, the Szent-Gy?rgyi-Krebs cycle) ? is a series of enzyme-catalysed chemical reactions of central importance in all living cell s that use oxygen as part of cellular respiration....
include:

Enzymes that catalyze decarboxylations are called decarboxylases or, more formally, carboxy-lyases

Carboxy-lyases

Carboxy-lyases, also known as decarboxylases, are carbon-carbon lyases lyases that add or remove a carboxyl group from organic compounds....
(EC number

EC number

The Enzyme Commission number is a numbering scheme scheme for enzymes, based on the chemical reactions they catalysis.As a system of enzyme nomenclature, every EC number is associated with a recommended name for the respective enzyme....
4.1.1).

Heating or pyrolysis of ?9-Tetrahydrocannabinolic acid yields the psychoactive compound ?9-Tetrahydrocannabinol

Tetrahydrocannabinol

Tetrahydrocannabinol , also known as THC, ?9-THC, ?9-tetrahydrocannabinol, ?1-tetrahydrocannabinol , or dronabinol, is the main psychoactive substance found in the Cannabis plant....
.

In organic chemistry
In retrosynthesis, decarboxylation reactions can be considered the opposite of homologation reaction

Homologation reaction

A homologation reaction, also known as homologization, is any chemical reaction that effects an overall increase of the carbon skeleton of a saturated reactant molecule....
s, in that the chain length becomes one carbon shorter.

Many carboxylic acids can be decarboxylated with heating.

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Encyclopedia

Decarboxylation is any chemical reaction

Chemical reaction

Carbon dioxide

Common examples

Common biosynthetic

Biosynthesis

Amino acid

Amine

tryptophan
Tryptophan

Tryptophan is one of the 20 List of standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG....
to tryptamine
Tryptamine

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived....
phenylalanine
Phenylalanine

Phenylalanine is an a-amino acid with the chemical formula HO2CCHCH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects....
to phenylethylamine
tyrosine
Tyrosine

Tyrosine or 4-hydroxyphenylalanine, is one of the 20 amino acids that are used by cell to protein biosynthesis proteins. This is a non-essential amino acid and it is found in casein....
to tyramine
Tyramine

In organic chemistry chemistry tyramine is a monoamine Chemical compound derived from the amino acid tyrosine. Tyramine can cause the release of stored monoamines, such as dopamine, norepinephrine, and epinephrine....
histidine
Histidine

Histidine is one of the 20 standard amino acids present in proteins. In the nutritional sense, in humans, histidine is considered an essential amino acid, but only in children....
to histamine
Histamine

Histamine is a biogenic amine involved in local immune system as well as regulating physiological function in the gut and acting as a neurotransmitter....
serine
Serine

Serine is an organic compound with the chemical formula hydrogenoxygen2carbonCHCH2OH....
to ethanolamine
Ethanolamine

Ethanolamine, also called 2-aminoethanol or monoethanolamine , is an organic chemical compound that is both a primary amine and a primary alcohol ....
glutamic acid
Glutamic acid

Glutamic acid is one of the 20 proteinogenic amino acids and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salt of glutamic acid are known as glutamates....
to GABA
Gabâ

Gab? or gabaa, for the Cebuano people , is the concept of a non-human and non-divine, imminent Retributive justice. A sort of negative karma, it is generally seen as an evil effect on a person because of their wrongdoings or transgressions....
lysine
Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
to cadaverine
Cadaverine

Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH25NH2, which is similar to putrescine....
arginine
Arginine

Arginine is an a-amino acid. The Optical isomerism is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA, CGG, AGA, and AGG....
to agmatine
Agmatine

Agmatine is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is discussed as a putative neurotransmitter....
ornithine
Ornithine

Ornithine is an amino acid which plays a role in the urea cycle....
to putrescine
Putrescine

Putrescine is an organic chemical compound NitrogenHydrogen24NH2 . It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses....
5-HTP to serotonin
Serotonin

Serotonin is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system and enterochromaffin cells in the gastrointestinal tract of animals including humans....
L-DOPA to dopamine
Dopamine

Dopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. In the human brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors ? D1, D2, D3, D4 and D5, and their variants....

Other decarboxylation reactions from the citric acid cycle

Citric acid cycle

pyruvate to acetyl-CoA
oxalosuccinate
Oxalosuccinic acid

Oxalosuccinic acid is a substrate of the citric acid cycle. It is acted upon by isocitrate dehydrogenase. Salts and esters of oxalosuccinic acid are known as oxalosuccinates....
to a-ketoglutarate
Ketoglutaric acid

a-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. Its anion, a-ketoglutarate is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle....
a-ketoglutarate
Ketoglutaric acid

a-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. Its anion, a-ketoglutarate is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle....
to succinyl-CoA.

Enzymes that catalyze decarboxylations are called decarboxylases or, more formally, carboxy-lyases

Carboxy-lyases

Carboxy-lyases, also known as decarboxylases, are carbon-carbon lyases lyases that add or remove a carboxyl group from organic compounds....
(EC number

EC number

Tetrahydrocannabinol

In organic chemistry

In retrosynthesis, decarboxylation reactions can be considered the opposite of homologation reaction

Homologation reaction

Solubility

Solubility is often seen as a property of a substance; for instance the solubility of a solid substance usually refers to the concentration of the substance in a liquid that has reached equilibrium with the substance in solid phase ....
/immiscible

Miscibility

Miscibility is a term commonly used in chemistry that refers to the property of liquids to mix in all proportions, forming a Homogeneity solution....
. Examples include mineral oil

Mineral oil

Mineral oil or liquid petroleumis a by-product in the distillation of petroleum to produce gasoline and other petroleum based products from crude oil....
and glycerol

Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
, depending on the acid's polarity

Polarity

In physics, polarity is a description of an attribute, typically a binary attribute , or a vector . For example:* An electric charge has a polarity of either positive or negative....
. After a certain temperature is reached, the carboxyl group will be removed from the acid to form the decarboxylation product and CO₂

Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
. Simpler acids are not as willing to undergo decarboxylation in this manner.

Occasionally, catalysts such as higher boiling-point ketones or metals, mainly copper

Copper

Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
are used in this process to obtain better yields and/or reaction time. The addition of catalytic amounts of cyclohexen-2-one has been reported to catalyze the decarboxylation of amino acids. However, using such catalysts may also yield an amount of unwanted by-products.

Pyrolysis

Pyrolysis

Pyrolysis is the chemical decomposition of a condensed substance by heating. The word is coined from the Greek language-derived morphemes pyro "fire" and lysys "decomposition"....
of carboxylic acids also yields the decarboxylation product, however the products formed are usually prone to undergo further thermal decomposition

Thermal decomposition

Thermal decomposition, also called thermolysis, is defined as a chemical reaction when a chemical substance breaks up into at least two chemical substances when heated....
under those conditions.

Heating a carboxylic acid strongly with soda lime

Soda lime

Soda lime is a mixture of chemicals, used in granular form in closed breathing environments, such as general anaesthesia, submarines, rebreathers and recompression chambers, to remove carbon dioxide from breathing gases to prevent CO%E2%82%82_retention and carbon dioxide poisoning....
is also able to affect decarboxylation. Heating the product of the malonic ester synthesis

Malonic ester synthesis

The malonic ester synthesis is a chemical reaction where diethyl malonate or another ester of malonic acid is alkylated at the carbon Alpha carbon to both carbonyl groups, and then converted to a substituted acetic acid....
with hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
also affords decarboxylation.

Depending on the conditions of the reaction, a decarboxylation can yield anywhere from 20% to nearly quantitative yields.

Decarboxylations are especially easy for beta-keto acid

Keto acid

Keto acids are organic compound acids containing a ketone functional group and a carboxylic acid group.Common types of keto acids include:...
s due to the formation of a cyclic transition state

Transition state

The transition state of a chemical reaction is a particular configuration along the reaction coordinate. It is defined as the state corresponding to the highest energy along this reaction coordinate....
for instance in Knoevenagel condensation

Knoevenagel condensation

The Knoevenagel condensation reaction is an organic reaction named after Emil Knoevenagel. It is a modification of the Aldol condensation .A Knoevenagel condensation is a nucleophilic addition of an active hydrogen compound to a carbonyl group followed by a dehydration reaction in which a molecule of water is eliminated ....
s. The Barton decarboxylation, Kolbe electrolysis

Kolbe electrolysis

Kolbe electolysis or Kolbe reaction is an organic reaction named after Adolph Wilhelm Hermann Kolbe. The Kolbe reaction is formally a decarboxylative dimerisation and proceeds by a free radical reaction mechanism....
and Hunsdiecker reaction

Hunsdiecker reaction

The Hunsdiecker reaction is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides. It is an example of a halogenation reaction....
are radical reactions. The Krapcho decarboxylation

Krapcho decarboxylation

The Krapcho decarboxylation is the chemical reaction of esters with halide anions. The ester must contain an electron-withdrawing group in the beta position, such as ?-ketoesters, malonic esters, a-cyanoesters, or a-sulfonylesters....
is a related decarboxylation of an ester.

Decarboxylation

Common examples

In organic chemistry

See also