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; achilleaic acid; acinitic acid
Identifiers
CAS Number	499-12-7 ; 585-84-2 (cis) ; 4023-65-8 (trans) ;
ChemSpider	303 (cis) ;
ECHA InfoCard	100.007.162
PubChem CID	309 (cis and trans);
UNII	93371T1BXP ; OF5471ZHRR (cis) ; 7DB37960CW (trans) ;
CompTox Dashboard (EPA)	DTXSID9060102 ;
	InChI InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3 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;
Properties
Chemical formula	C6H6O6
Molar mass	174.108 g·mol−1
Appearance	Colorless crystals
Melting point	190 °C (374 °F; 463 K) (decomposes) (mixed isomers), 173 °C (cis and trans isomers)
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)₂C(OH)CO₂H → HO₂CCH=C(CO₂H)CH₂CO₂H + H₂O

A mixture of isomers are generated in this way.

It was first prepared by thermal dehydration.[4]

References

"Aconitic Acid - Compound Summary (CID 309)". PubChem.
Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for Biochemical Research (3rd ed.). Oxford: Clarendon Press. ISBN 9780198552994.
Bruce, W. F. (1937). "Aconitic Acid". 17: 1. doi:10.15227/orgsyn.017.0001. Cite journal requires |journal= (help)
Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" [Substitution products of citric acid and an attempt at the synthesis of the latter]. Justus Liebig's Annalen der Chemie. 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.

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[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". 17: 1. doi:10.15227/orgsyn.017.0001. Cite journal requires |journal= (help)

[4] Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" [Substitution products of citric acid and an attempt at the synthesis of the latter]. Justus Liebig's Annalen der Chemie. 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.