Aconitic acid

Aconitic acid
cis-Aconitic acid (top) and trans-Aconitic acid (bottom)[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 YesY
PubChem 309
ChemSpider 303 YesY
UNII 93371T1BXP YesY
MeSH Aconitate
ChEBI CHEBI:22211 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H6O6
Molar mass 174.11 g mol−1
Appearance Colorless crystals
Melting point

190 °C (decomp) (trans isomer), 122 °C (cis isomer)
Acidity (pKa) 2.80, 4.46 (trans isomer) [2]
 YesY acid (verify) (what is: YesY/N?)
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 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

  1. ^ cis-aconitate - Compound Summary, PubChem
  2. '^ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  3. ^ William F. Bruce (1943), "Aconitic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0012 ; Coll. Vol. 2: 12 
  4. ^ B. Pawolleck,"Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren" Justus Liebig's Annalen der Chemie 1875, volume 178, 150-170. doi:10.1002/jlac.18751780203


v · d · eCitric Acid Cycle Metabolic Pathway
Oxaloacetate Malate Fumarate Succinate Succinyl-CoA
Oxaloacetate wpmp.png S-malate wpmp.png Fumarate wpmp.png Succinate wpmp.png Succinyl-CoA wpmp.png
Biochem reaction arrow reverse NNYY horiz med.png Biochem reaction arrow reverse NNYN horiz med.png Biochem reaction arrow reverse NNYY horiz med.png Biochem reaction arrow reverse NNYY horiz med.png
Acetyl-CoA NADH + H+ NAD+ H2O FADH2 FAD CoA + ATP(GTP) Pi + ADP(GDP)
Acetyl co-A wpmp.png + H2O Biochem reaction arrow special 1.png Biochem reaction arrow special 2.png NADH + H+ + CO2
CoA NAD+
Citrate wpmp.png H2O Cis-Aconitate wpmp.png H2O Threo-Ds-isocitrate wpmp.png NAD(P)+ NAD(P)H + H+ Oxalosuccinate wpmp.png CO2 2-oxoglutarate wpmp.svg
Biochem reaction arrow foward NYNN horiz med.png Biochem reaction arrow foward YNNN horiz med.png Biochem reaction arrow foward YYNN horiz med.png Biochem reaction arrow foward NYNN horiz med.png
Citrate cis-Aconitate Isocitrate Oxalosuccinate α-Ketoglutarate

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

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Look at other dictionaries:

  • aconitic acid — |akə|nid.ik noun Etymology: International Scientific Vocabulary aconite + ic : a white crystalline acid C3H3(COOH)3 known in cis and trans forms that occurs in aconite, sugar cane, and beet root and is obtained as a byproduct in sugar manufacture …   Useful english dictionary

  • aconitic acid — akonito rūgštis statusas T sritis chemija formulė HOOCCH=C(COOH)CH₂COOH atitikmenys: angl. aconitic acid rus. аконитовая кислота ryšiai: sinonimas – 1,2,3 propentrikarboksirūgštis …   Chemijos terminų aiškinamasis žodynas

  • aconitic acid — noun An organic acid involved in the isomerisation of citrate to isocitrate in the citric acid cycle. Syn: achilleic acid, citridinic acid, equisetic acid, pyrocitric acid …   Wiktionary

  • aconitic acid — ac·o·nit·ic acid .ak ə .nit ik n a white crystalline acid C3H3(COOH)3 that occurs in aconite, sugarcane, and beet roots and is obtained as a by product in sugar manufacture or by dehydration of citric acid by sulfuric acid …   Medical dictionary

  • cis-aconitic acid — Dehydration product of citric acid; an enzyme bound intermediate in the tricarboxylic acid cycle …   Medical dictionary

  • cis-aconitic acid — /ˌsɪs ˌækənɪtɪk ˈæsəd/ (say .sis .akuhnitik asuhd) noun a tricarboxylic acid, HOOC.CH2.C(COOH)=CH.COOH, formed from citrate, an intermediate in the citric acid cycle …  

  • aconitic — adjective a) Of or pertaining to aconite. b) Of or pertaining to aconitic acid …   Wiktionary

  • Aconitic — Ac o*nit ic, a. 1. Of or pertaining to aconite. [1913 Webster] 2. (Chem.) Pert. to or designating a crystalline tribasic acid, {C6H6O6}, obtained from aconite and other plants. It is a carboxyl derivative of itaconic acid. Both the natural forma… …   The Collaborative International Dictionary of English

  • itaconic acid — noun a crystalline carboxylic acid; occurs in some fermentations of sugars • Hypernyms: ↑acid * * * | ̷ ̷ ̷ ̷| ̷ ̷ nik noun Etymology: International Scientific Vocabulary, anagram of aconitic : a crystalline dicarboxylic acid HOOCC( . CH2)CH2COOH …   Useful english dictionary

  • aconic acid — əˈkänik , aˈ noun Etymology: contraction of aconitic : a crystalline lactonic acid C4H3O2COOH formed indirectly from aconitic acid …   Useful english dictionary

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