''trans''-Glutaconic acid is an

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 ...

with

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

HO₂CCH=CHCH₂CO₂H. This

dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic.Boy Cornils, Peter Lappe "Dicarbox ...

exists as a colorless solid and is related to the

saturated Saturation, saturated, unsaturation or unsaturated may refer to: Chemistry *Saturated and unsaturated compounds, a classification of compounds related to their ability to resist addition reactions **Degree of unsaturation **Saturated fat or satur ...

chemical

glutaric acid Glutaric acid is the organic compound with the formula C3H6(COOH)2. 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 o ...

, HO₂CC(CH₂)₃CO₂H.

Ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s and salts of glutaconic acid are called glutaconates. Glutaconate bound to

coenzyme A Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the Fatty acid metabolism#Synthesis, synthesis and Fatty acid metabolism#.CE.B2-Oxidation, oxidation of fatty acids, and the oxidation of pyruvic acid, pyruvate in the citric ac ...

glutaconyl-CoA Glutaconyl-CoA is an intermediate in the metabolism of lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolv ...

, is an intermediate in

lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group ( ...

metabolism.

Related compounds

The

geometric isomer Geometry (; ) is a branch of mathematics concerned with properties of space such as the distance, shape, size, and relative position of figures. Geometry is, along with arithmetic, one of the oldest branches of mathematics. A mathematician w ...

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

levulinic acid Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the chemical formula, formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from d ...

followed by treatment of the dibromoketone with potassium carbonate. Glutaconic

anhydride An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid (chemistry), acid. In organic chemistry, organic acid anhydrides contain the functional group . Organic acid anhydrides often form when one ...

, which forms by dehydration the

diacid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic.Boy Cornils, Peter Lappe "Dicarboxyli ...

, exists mainly as the dicarbonyl

tautomer In chemistry, tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the reloca ...

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.{{cite journal , author1=Briggs, S. P., author2=Davies, D. I., author3=Newton, R. F., author4=Reynolds, D. P. , title= The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene , volume= 146 , journal= J. Chem. Soc. Perkin Trans. 1 , year= 1981 , pages= 146–149 , doi= 10.1039/P19810000146

Medical aspects

Glutaric, 3-hydroxyglutaric, and glutaconic acids are structurally related

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 ...

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

References

Enoic acids Dicarboxylic acids