Aconitic acid

Aconitic acid[1]
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
PubChem	309
MeSH	Aconitate
SMILES	O=C(O)CC(=CC(=O)O)C(=O)O
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)
InChI key	GTZCVFVGUGFEME-UHFFFAOYAL
ChemSpider ID	303
Properties
Molecular formula	C6H6O6
Molar mass	174.108 g/mol
Appearance	colourless crystals
Melting point	198-199°C (decomp)
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase.

Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:^[2]

(HO₂CCH₂)₂COH(CO₂H) → HO₂CCH=C(CO₂H)CH₂CO₂H + H₂O

It was first prepared by thermal dehydration.^[3]

References

v • d • e 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