glutaconic acid
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461121958
| ImageFileL1 = Glutaconic acid trans vinyl-H.png
| ImageSizeL1 = 120
| ImageCaptionL1 = trans
| ImageFileR1 = Glutaconic acid cis vinyl-H.png
| ImageSizeR1 = 120
| ImageCaptionR1 = cis
| ImageFileL2 = (E)-Glutaconic-acid-3D-spacefill.png
| ImageSizeL2 = 130
| ImageAltL2 = Space-filling model of the trans isomer
| ImageFileR2 = (Z)-Glutaconic-acid-3D-spacefill.png
| ImageSizeR2 = 130
| ImageAltR2 = Space-filling model of the cis isomer
| IUPACName = Pent-2-enedioic acid
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444138
| InChI = 1/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
| InChIKey = XVOUMQNXTGKGMA-OWOJBTEDBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XVOUMQNXTGKGMA-OWOJBTEDSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1724-02-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NOH8K33D47
| CASNo_Comment = (unspecified)
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 628-48-8
| CASNo1_Comment = (trans)
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 505-36-2
| CASNo2_Comment = (cis)
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 557347
| PubChem = 5280498
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15670
| SMILES = O=C(O)\C=C\CC(=O)O
}}
|Section2={{Chembox Properties
| Formula = C5H6O4
| MolarMass = 130.099 g/mol
| Appearance = Colorless solid
| Density =
| MeltingPtC = 137 to 139
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.
Glutaconate bound to coenzyme A, glutaconyl-CoA, is an intermediate in lysine metabolism.{{Cite book |last=Voet |first=Donald |title=Biochemistry |last2=Voet |first2=Judith G. |date=2011 |publisher=Wiley |isbn=978-0-470-57095-1 |edition=4 |location=Hoboken, NJ |pages=1040{{--}}1041}}
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.{{cite journal |author1=Buckel, W.|author2=Pierik, A. J.|author3=Plett, S.|author4=Alhapel, A.|author5=Suarez, D.|author6=Tu, S.-m.|author7=Golding, B. T. |title= Mechanism-Based Inactivation of Coenzyme B12-Dependent 2-Methyleneglutarate Mutase by (Z)-Glutaconate and Buta-1,3-diene-2,3-dicarboxylate |journal= Eur. J. Inorg. Chem. |year= 2006 |volume=2006 |issue= 18 |pages= 3622–3626 |doi= 10.1002/ejic.200600405}}
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.{{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 metabolites. In glutaric aciduria type 1, glutaconic acid accumulates, resulting in brain damage.