Aconitic acid

Aconitic acid^[1]
	200px; cis-aconitic acid
	200px; 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
ChEBI	CHEBI:22211
ChemSpider	[http://www.chemspider.com/Chemical-Structure.303 _TEMPHERE_ = QQQ QQQ.html 303 _TEMPHERE_ = QQQ QQQ]
Jmol 3D model	Interactive image
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)
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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

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Names
200px cis-aconitic acid
200px trans-aconitic acid
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^Y
ChEBI	CHEBI:22211^Y
ChemSpider	[http://www.chemspider.com/Chemical-Structure.303 _TEMPHERE_ = QQQ^YQQQ.html 303 _TEMPHERE_ = QQQ^YQQQ]^N
Jmol 3D model	Interactive image
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)^Y Key: GTZCVFVGUGFEME-UHFFFAOYSA-N^Y 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 (pK_a)	2.80, 4.46 (trans isomer)^[2]
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references