Aconitic acid refers to
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 ...
s with the formula . A white solid, it is classified as a tricarboxylic acid. The two
isomers
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the existence or possibili ...
are ''cis''-aconitic acid and ''trans''-aconitic acid. The
conjugate base
A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid gives a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as it loses a hydrogen ion in the reve ...
of ''cis''-aconitic acid, ''cis''-aconitate is an intermediate in the
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
ization of
citrate
Citric acid is an organic compound with the formula . It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry
Biochemistry, or biological chemistry, is the study of chemical processes within and relati ...
to
isocitrate
Isocitric acid is a structural isomer of citric acid. Since citric acid and isocitric acid are structural isomers, they share similar physical and chemical properties. Due to these similar properties, it is difficult to separate the isomers. Salts ...
in the
citric acid cycle
The citric acid cycle—also known as the Krebs cycle, Szent–Györgyi–Krebs cycle, or TCA cycle (tricarboxylic acid cycle)—is a series of chemical reaction, biochemical reactions that release the energy stored in nutrients through acetyl-Co ...
. It is acted upon by the enzyme
aconitase
Aconitase (aconitate hydratase; ) is an enzyme that catalyses the stereochemistry, stereo-specific isomerization of citrate to isocitrate via ''cis''-aconitate in the tricarboxylic acid cycle, a non-redox-active process.
Image:Citrate wpmp.p ...
.
Aconitic acid can be synthesized by dehydration of
citric acid
Citric acid is an organic compound with the formula . It is a Transparency and translucency, colorless Weak acid, weak organic acid. It occurs naturally in Citrus, citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, ...
using
sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
:
:(HO
2CCH
2)
2C(OH)CO
2H → HO
2CCH=C(CO
2H)CH
2CO
2H + H
2O
A mixture of isomers is generated in this way.
Aconitic acid was originally isolated from ''
Aconitum napellus
''Aconitum napellus'', monkshood, aconite, Venus' chariot or wolfsbane, is a species of highly toxic flowering plants in the genus ''Aconitum'' of the family Ranunculaceae, native and endemic to western and central Europe. It is an herbaceous pe ...
'' by Swiss chemist and apothecary
Jacques Peschier in 1820. It was first prepared by thermal dehydration.
Like the conjugate bases of other
polycarboxylic acid, acotinic acid forms a variety of
coordination complex
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...
es. One example is the
coordination polymer
Coordination may refer to:
* Coordination (linguistics), a compound grammatical construction
* Coordination complex, consisting of a central atom or ion and a surrounding array of bound molecules or ions
** A chemical reaction to form a coordinat ...
3(C6H3O6)2(H2O)6">n3(C6H3O6)2(H2O)6sub>n.
References
{{Citric acid cycle
Tricarboxylic acids
Enoic acids