Aconitic acid

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cis-Aconitic acid (top) and trans-Aconitic acid (bottom)[1]
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
499-12-7 YesY
ChEBI CHEBI:22211 YesY
ChemSpider [http://www.chemspider.com/Chemical-Structure.303

_TEMPHERE_ = QQQ YesYQQQ.html 303 _TEMPHERE_ = QQQ YesYQQQ] N

Jmol-3D images Image
MeSH Aconitate
PubChem 309
Properties
C6H6O6
Molar mass 174.11 g·mol−1
Appearance Colorless crystals
Melting point 190 °C (374 °F; 463 K) (decomposes) (trans isomer), 122 °C (cis isomer)
Acidity (pKa) 2.80, 4.46 (trans isomer)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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:[3]

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

It was first prepared by thermal dehydration.[4]

References[edit]

  1. ^ "Aconitic Acid - Compound Summary (CID 309)". PubChem. 
  2. ^ Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for Biochemical Research (3rd ed.). Oxford: Clarendon Press. ISBN 9780198552994. 
  3. ^ Bruce, W. F. (1937). "Aconitic Acid". Org. Synth. 17: 1. ; Coll. Vol. 2, p. 12 
  4. ^ Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren". Justus Liebig's Annalen der Chemie 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.