trans-Glutaconic acid is an organic compound

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...

 with formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 HO₂CCH=CHCH₂CO₂H. This dicarboxylic acid

Dicarboxylic acid

Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group...

 exists as a colorless solid and is related to the saturated

Saturation (chemistry)

In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...

 chemical glutaric acid

Glutaric acid

Glutaric acid is the organic compound with the formula HO2C3CO2H. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%....

, HO₂CC(CH₂)₃CO₂H. Ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

s and salts of glutaconic acid are called glutaconates.

Related compounds

The geometric isomer

Geometric isomerism

In organic chemistry, cis/trans isomerism or geometric isomerism or configuration isomerism or E/Z isomerism is a form of stereoisomerism describing the orientation of functional groups within a molecule...

, cis-glutaconic acid, has a noticeably lower melting point (130–132 °C). It can be prepared by bromination of levulinic acid

Levulinic acid

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3CCH2CH2CO2H. It is a keto acid. This white crystalline is soluble in water, ethanol, and diethyl ether.-Synthesis and uses:...

 followed by treatment of the dibromoketone with potassium carbonate.

Glutaconic anhydride, which forms by dehydration the diacid

Dicarboxylic acid

Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group...

, exists mainly as the dicarbonyl tautomer

Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. This reaction commonly results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond...

 in solution. It is a colorless solid melting at 77–82 °C. Either the cis or trans diacid can be used to make it: the trans form isomerizes under the reaction conditions.

Medical aspects

Glutaric

Glutaric acid

Glutaric acid is the organic compound with the formula HO2C3CO2H. Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%....

, 3-hydroxglutaric, and glutaconic acids are structurally related metabolite

Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...

s. In Glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage.