Misplaced Pages

Glutaconic acid

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by CheMoBot (talk | contribs) at 09:06, 9 August 2011 (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 09:06, 9 August 2011 by CheMoBot (talk | contribs) (Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
Glutaconic acid
trans
cis
Names
IUPAC name Pent-2-enedioic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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.

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.

Medical aspects

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

References

  1. "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. (18): 3622–3626. 2006. doi:10.1002/ejic.200600405. {{cite journal}}: Unknown parameter |authors= ignored (help)
  2. "The Structure of Glutaconic Anhydride and the Synthetic Utility of its Diels–Alder Adduct with Cyclopentadiene". J. Chem. Soc. Perkin Trans I. 146: 146–149. 1981. doi:10.1039/P19810000146. {{cite journal}}: Unknown parameter |authors= ignored (help)
Categories: