Aconitic acid

Aconitic acid^[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
CAS Number	499-12-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:22211
ChemSpider	[http://www.chemspider.com/Chemical-Structure.303 _TEMPHERE_ = QQQQQQ.html 303 _TEMPHERE_ = QQQQQQ]
ECHA InfoCard	100.007.162
MeSH	Aconitate
PubChem	309
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	174.11 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

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.