Aconitic acid
Chemical compound
From Wikipedia, the free encyclopedia
Aconitic acid refers to organic compounds with the formula HO2CCH2C(CO2H)=CHCO2H. A white solid, it is classified as a tricarboxylic 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.
cis-aconitic acid | |
 trans-aconitic acid | |
| Names | |
|---|---|
| Preferred 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 | |
| ChemSpider |
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| ECHA InfoCard | 100.007.162 |
PubChem CID |
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| UNII |
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CompTox Dashboard (EPA) |
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| Properties | |
| 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] 2.78, 4.41, 6.21 (cis isomer)[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:[4]
- (HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H + H2O
A mixture of isomers is generated in this way.
Aconitic acid was originally isolated from Aconitum napellus by Swiss chemist and apothecary Jacques Peschier in 1820.[5][6] It was first prepared by thermal dehydration.[7]
Like the conjugate bases of other polycarboxylic acid, acotinic acid forms a variety of coordination complexes. One example is the coordination polymer [Zn3(C6H3O6)2(H2O)6]n.[8]