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Aconitic acid

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cis-Aconitic acid (top) and trans-Aconitic acid (bottom)
cis-Aconitic acid
trans-Aconitic acid
Names
IUPAC name Prop-1-ene-1,2,3-tricarboxylic acid
Other names Achilleic acid; Equisetic acid; Citridinic acid; Pyrocitric acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.162 Edit this at Wikidata
MeSH Aconitate
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)Key: GTZCVFVGUGFEME-UHFFFAOYSA-N
  • InChI=1/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)Key: GTZCVFVGUGFEME-UHFFFAOYAL
SMILES
  • O=C(O)CC(=CC(=O)O)C(=O)O
Properties
Chemical formula C6H6O6
Molar mass 174.108 g·mol
Appearance Colorless crystals
Melting point 190 °C (decomp) (trans isomer), 122 °C (cis isomer)
Acidity (pKa) 2.80, 4.46 (trans isomer)
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

Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon by the enzyme aconitase.

Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:

(HO2CCH2)2COH(CO2H) → HO2CCH=C(CO2H)CH2CO2H + H2O

It was first prepared by thermal dehydration.

References

  1. cis-aconitate - Compound Summary, PubChem
  2. ' Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  3. William F. Bruce (1943). "Aconitic Acid". Organic Syntheses; Collected Volumes, vol. 2, p. 12.
  4. B. Pawolleck,"Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" Justus Liebig's Annalen der Chemie 1875, volume 178, 150-170. doi:10.1002/jlac.18751780203
Citric acid cycle metabolic pathway

Acetyl-CoA

+ H2O

Oxaloacetate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightNADH +H NAD

Malate

Leftward reaction arrow with minor substrate(s) from bottom right  H2O

Fumarate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightFADH2 FAD

Succinate

Leftward reaction arrow with minor product(s) to bottom left and minor substrate(s) from bottom rightCoA + ATP (GTP) Pi + ADP (GDP)

Succinyl-CoA

NADH + H + CO2
CoA NAD

Citrate

  H2O Rightward reaction arrow with minor product(s) to top right

cis-Aconitate

H2O   Rightward reaction arrow with minor substrate(s) from top left

Isocitrate

NAD(P) NAD(P)H +  H Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right

Oxalosuccinate

  CO2 Rightward reaction arrow with minor product(s) to top right

2-oxoglutarate

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