Glutaconic acid

Glutaconic acid

trans cis
Names
IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number	628-48-8 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15670 Y
ChemSpider	4444138 Y
PubChem CID	5280498
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  (what is YN ?)
Infobox references

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.

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.

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.

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