''trans''-Glutaconic acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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 betwee ...

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. In general, dicarboxylic acids show ...

exists as a colorless solid and is related to the

saturated Saturation, saturated, unsaturation or unsaturated may refer to: Chemistry * Saturation, a property of organic compounds referring to carbon-carbon bonds ** Saturated and unsaturated compounds **Degree of unsaturation ** Saturated fat or fatty ac ...

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 ...

, HO₂CC(CH₂)₃CO₂H.

Ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s and salts of glutaconic acid are called glutaconates.

Related compounds

The

geometric isomer Geometry (; ) is, with arithmetic, one of the oldest branches of mathematics. It is concerned with properties of space such as the distance, shape, size, and relative position of figures. A mathematician who works in the field of geometry is ...

, ''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 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 degradation of cell ...

followed by treatment of the dibromoketone with potassium carbonate. Glutaconic

anhydride An organic acid anhydride is an acid anhydride that is an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the pa ...

, 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. In general, dicarboxylic acids show ...

, exists mainly as the dicarbonyl

tautomer 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 relocation of a hydr ...

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 Glutaric acidemia type 1 (GA1) is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine and tryptophan. Excessive levels of their intermediate breakdown products (glutaric acid, glutaryl-C ...

, glutaconic acid accumulates, resulting in brain damage.

References

Enoic acids Dicarboxylic acids