Glutaconic acid

Glutaconic acid
trans	cis
Names
	IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number	1724-02-3 (unspecified) ; 628-48-8 (trans) ; 505-36-2 (cis) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15670 ;
ChEMBL	ChEMBL557347 ;
ChemSpider	4444138 ;
PubChem CID	5280498;
UNII	NOH8K33D47 ;
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+ Key: XVOUMQNXTGKGMA-OWOJBTEDSA-N ; 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). verify (what is ?) 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.

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.

References

^ Voet, Donald; Voet, Judith G. (2011). Biochemistry (4 ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-57095-1.
^ Buckel, W.; Pierik, A. J.; Plett, S.; Alhapel, A.; Suarez, D.; Tu, S.-m.; Golding, B. T. (2006). "Mechanism-Based Inactivation of Coenzyme B₁₂-Dependent 2-Methyleneglutarate Mutase by (Z)-Glutaconate and Buta-1,3-diene-2,3-dicarboxylate". Eur. J. Inorg. Chem. 2006 (18): 3622–3626. doi:10.1002/ejic.200600405.
^ Briggs, S. P.; Davies, D. I.; Newton, R. F.; Reynolds, D. P. (1981). "The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene". J. Chem. Soc. Perkin Trans. 1. 146: 146–149. doi:10.1039/P19810000146.

[1] Voet, Donald; Voet, Judith G. (2011). Biochemistry (4 ed.). Hoboken, NJ: Wiley. pp. 1040–1041. ISBN 978-0-470-57095-1.

[2] Buckel, W.; Pierik, A. J.; Plett, S.; Alhapel, A.; Suarez, D.; Tu, S.-m.; Golding, B. T. (2006). "Mechanism-Based Inactivation of Coenzyme B₁₂-Dependent 2-Methyleneglutarate Mutase by (Z)-Glutaconate and Buta-1,3-diene-2,3-dicarboxylate". Eur. J. Inorg. Chem. 2006 (18): 3622–3626. doi:10.1002/ejic.200600405.

[3] Briggs, S. P.; Davies, D. I.; Newton, R. F.; Reynolds, D. P. (1981). "The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene". J. Chem. Soc. Perkin Trans. 1. 146: 146–149. doi:10.1039/P19810000146.

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