Glutaconic acid

trans-Glutaconic acid is an organic compound with formula HO₂CCH=CHCH₂CO₂H. This dicarboxylic acid exists as a colorless solid and is related to the saturated chemical glutaric acid, HO₂CC(CH₂)₃CO₂H. Esters and salts of glutaconic acid are called glutaconates.

Glutaconic acid

trans cis
Names
IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number	1724-02-3 (unspecified) Y 628-48-8 (trans) Y 505-36-2 (cis) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15670 Y
ChEMBL	ChEMBL557347 Y
ChemSpider	4444138 Y
PubChem CID	5280498
UNII	NOH8K33D47 Y
CompTox Dashboard (EPA)	DTXSID70211883
InChI InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+ Y Key: XVOUMQNXTGKGMA-OWOJBTEDSA-N Y InChI=1/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+ Key: XVOUMQNXTGKGMA-OWOJBTEDBR
SMILES O=C(O)\C=C\CC(=O)O
Properties
Chemical formula	C5H6O4
Molar mass	130.099 g/mol
Appearance	Colorless solid
Melting point	137 to 139 °C (279 to 282 °F; 410 to 412 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Glutaconate bound to coenzyme A, glutaconyl-CoA, is an intermediate in lysine metabolism.^[1]

Related compounds

The geometric isomer, cis-glutaconic acid, has a noticeably lower melting point (130–132 °C). It can be prepared by bromination of levulinic acid followed by treatment of the dibromoketone with potassium carbonate.^[2]

Glutaconic anhydride, which forms by dehydration the diacid, exists mainly as the dicarbonyl tautomer 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.^[3]

Medical aspects

Glutaric, 3-hydroxyglutaric, and glutaconic acids are structurally related metabolites. In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage.