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.
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 |
|
ECHA InfoCard | 100.007.162 |
PubChem CID
|
|
UNII |
|
CompTox Dashboard (EPA)
|
|
| |
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] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid:[3]
- (HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H + H2O
A mixture of isomers are generated in this way.
Aconitic acid was originally isolated from Aconitum napellus by Swiss chemist and apothecary Jacques Peschier in 1820.[4][5] It was first prepared by thermal dehydration.[6]
References edit
- ^ "Aconitic Acid - Compound Summary (CID 309)". PubChem.
- ^ Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for Biochemical Research (3rd ed.). Oxford: Clarendon Press. ISBN 9780198552994.
- ^ Bruce, W. F. (1937). "Aconitic Acid". Organic Syntheses. 17: 1. doi:10.15227/orgsyn.017.0001.
- ^ Brande, William Thomas (1848). A Manual of Chemistry, Vol II (6 ed.). London: John W. Parker. p. 1344. Retrieved 8 November 2023.
- ^ Reichenbach, Karl-Rudolf (2001). Jacques Peschier (1769-1832): Ein Genfer Apotheker und Chemiker. Zürich: Wissenschaftliche Verlagsgesellschaft mbH Stuttgart. ISBN 3804719090. Retrieved 8 November 2023.
- ^ Pawolleck, B. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" [Substitution products of citric acid and an attempt at the synthesis of the latter]. Justus Liebig's Annalen der Chemie. 178 (2–3): 150–170. doi:10.1002/jlac.18751780203.