Aconitic acid

Quality 0.50 · 3 views · Updated 2 months ago

title: "Aconitic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tricarboxylic-acids", "enoic-acids"] topic_path: "general/tricarboxylic-acids" source: "https://en.wikipedia.org/wiki/Aconitic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477240926 | Name = Aconitic acid | ImageFile1 = Aconitic acid.svg | ImageClass1 = skin-invert | ImageSize1 = | ImageCaption1 = cis-aconitic acid | ImageFile2 = Trans-aconitic acid.png | ImageClass2 = skin-invert | ImageSize2 = | ImageCaption2 = trans-aconitic acid | PIN = Prop-1-ene-1,2,3-tricarboxylic acid | OtherNames = Achilleic acid; equisetic acid; citridinic acid; pyrocitric acid; achilleaic acid; acinitic acid | Reference = |Section1={{Chembox Identifiers | 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) | StdInChI_Ref = | StdInChI = 1S/C4H8/c1-3-4-2/h3-4H,1-2H3 | InChIKey = GTZCVFVGUGFEME-UHFFFAOYAL | StdInChIKey_Ref = | StdInChIKey = GTZCVFVGUGFEME-UHFFFAOYSA-N | PubChem1 = 309 | PubChem1_Comment = (cis and trans) | ChemSpiderID1_Ref = | ChemSpiderID1 = 303 | ChemSpiderID1_Comment = (cis) | SMILES1 = | SMILES1_Comment = (cis) | InChI1 = | InChI1_Comment = (cis) | InChIKey1 = | InChI3 = | InChI3_Comment = (cis) | InChIKey3 = | PubChem2 = | PubChem2_Comment = (trans) | ChemSpiderID2_Ref = | ChemSpiderID2 = | ChemSpiderID2_Comment = (trans) | SMILES2 = | SMILES2_Comment = (trans) | InChI2 = | InChI2_Comment = (trans) | InChIKey2 = | InChI4 = | InChI4_Comment = (trans) | InChIKey4 = | ChEBI_Ref = | ChEBI = | UNII_Ref = | UNII = 93371T1BXP | UNII1_Ref = | UNII1 = OF5471ZHRR | UNII1_Comment = (cis) | UNII2 = 7DB37960CW | UNII2_Ref = | UNII2_Comment = (trans) | SMILES = | CASNo = 499-12-7 | CASNo_Ref = | CASNo1 = 585-84-2 | CASNo1_Comment = (cis) | CASNo1_Ref = | CASNo2 = 4023-65-8 | CASNo2_Comment = (trans) | CASNo2_Ref = | EC_number = | ChemSpiderID_Ref = | ChemSpiderID = | RTECS = |Section2={{Chembox Properties | C=6 | H=6 | O=6 | Appearance = Colorless crystals | Density = | MeltingPtC = 190 | MeltingPt_notes = (decomposes) (mixed isomers), 173 °C (cis and trans isomers) | BoilingPt = | pKa = 2.80, 4.46 (trans isomer) 2.78, 4.41, 6.21 (cis isomer) |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Aconitic acid refers to organic compounds with the formula . 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.

Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid: :(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. It was first prepared by thermal dehydration.

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.

References

References

  1. "Aconitic Acid - Compound Summary (CID 309)". [[PubChem]].
  2. (1989). "Data for Biochemical Research". Clarendon Press.
  3. (2003). "Determination of all pKa values of some di- and tri-carboxylic unsaturated and epoxy acids and their polylinear correlation with the carboxylic group atomic charges". Journal of Chemical Research.
  4. Bruce, W. F.. (1937). "Aconitic Acid". Organic Syntheses.
  5. (1848). "A Manual of Chemistry, Vol II.". John W. Parker..
  6. (2001). "Jacques Peschier (1769-1832): Ein Genfer Apotheker und Chemiker". Wissenschaftliche Verlagsgesellschaft mbH Stuttgart.
  7. Pawolleck, B.. (1875). "Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren". Justus Liebig's Annalen der Chemie.
  8. (2009). "Synthesis and characterization of a novel photoluminescent three-dimensional metal–organic framework". Inorganica Chimica Acta.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

tricarboxylic-acidsenoic-acids