Chlorocitric acid is a
organochlorine compound
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...
, a derivative 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, ...
, belonging to the group of
tricarboxylic acids and their derivatives, characterized by the presence of three carboxyl groups. Its chemical formula is .
Natural occurrence
The acid has been detected in
human blood
Blood is a body fluid in the circulatory system of humans and other vertebrates that delivers necessary substances such as nutrients and oxygen to the cells, and transports metabolic waste products away from those same cells.
Blood is compo ...
. Chlorocitric acid is not a naturally occurring
metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism.
The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
; it is found exclusively in individuals who have been exposed to this compound or its derivatives. From a scientific perspective, chlorocitric acid is considered to be part of the human
exposome, which encompasses all exposures that individuals encounter throughout their lifetime and their impact on health. These exposures begin before birth and include environmental and occupational factors.
Synthesis
Chlorocitric acid is obtained by the action of
hypochlorous acid
Hypochlorous acid is an inorganic compound with the chemical formula , also written as HClO, HOCl, or ClHO. Its structure is . It is an acid that forms when chlorine dissolves in water, and itself partially dissociates, forming a hypochlorite an ...
on
aconitic acid
Aconitic acid refers to organic compounds with the formula . A white solid, it is classified as a tricarboxylic acid. The two isomers are ''cis''-aconitic acid and ''trans''-aconitic acid. The conjugate base of ''cis''-aconitic acid, ''cis''-aconi ...
in aqueus solution.
Physical properties
The acid is uncrystallizible, soluble in water and
ether
In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...
. The compound decomposes when heated, releasing
hydrochloric acid
Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
and oxycitric acid.
Uses
There are reports suggesting that chlorocitric acid might be used as an
anti-obesity agent.
[{{cite web , title=CHLOROCITRIC ACID WEIGHT REDUCTION EFFECT , url=https://insights.citeline.com/PS011493/CHLOROCITRIC-ACID-WEIGHT-REDUCTION-EFFECT/ , publisher=Citeline , access-date=9 April 2025 , language=en , date=23 February 1987]
See also
*
Fluorocitric acid
*
Hydroxycitric acid
*
Isocitric acid
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 ...
References
Organochlorides
Tricarboxylic acids