Aconitic acid

Aconitic acid

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 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:22211 Y
ChemSpider	[http://www.chemspider.com/Chemical-Structure.303 _TEMPHERE_ = QQQ YQQQ.html 303 _TEMPHERE_ = QQQ YQQQ] N
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) 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 (pKa)	2.80, 4.46 (trans isomer)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

_TEMPHERE_ = QQQ ^YQQQ.html 303 _TEMPHERE_ = QQQ ^YQQQ] ^N

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:

It was first prepared by thermal dehydration.