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 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)[2]
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

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

Citric acid cycle metabolic pathway
			Oxaloacetate			Malate			Fumarate			Succinate			Succinyl-CoA
Acetyl-CoA				NADH + H+	NAD+			H2O		FADH2	FAD		CoA + ATP(GTP)	Pi + ADP(GDP)
	+	H2O														NADH + H+ + CO2
		CoA														NAD+
					H2O		H2O			NAD(P)+	NAD(P)H + H+			CO2
			Citrate			cis-Aconitate			Isocitrate			Oxalosuccinate			α-Ketoglutarate