Jump to content

Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 References

Aconitic acid

●تۆرکجه ●Čeština ●Deutsch ●Español ●فارسی ●Français ●Galego ●한국어 ●Italiano ●Latviešu ●Magyar ●മലയാളം ●Bahasa Melayu ●Nederlands ●日本語 ●Polski ●Português ●Română ●Русский ●Slovenčina ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Suomi ●中文 Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version In other projects ●Wikimedia Commons Appearance From Wikipedia, the free encyclopedia

Aconitic acid^[1]
Names
cis-aconitic acid
trans-aconitic acid
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
CAS Number	499-12-7^Y 585-84-2 (cis)^Y 4023-65-8 (trans)^Y
ChemSpider	303 (cis)^N
ECHA InfoCard	100.007.162
PubChem CID	309 (cis and trans)
UNII	93371T1BXP^Y OF5471ZHRR (cis)^Y 7DB37960CW (trans)^Y
CompTox Dashboard (EPA)	DTXSID9060102
InChI InChI=1S/C4H8/c1-3-4-2/h3-4H,1-2H3^Y Key: GTZCVFVGUGFEME-UHFFFAOYSA-N^Y 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) Key: GTZCVFVGUGFEME-UHFFFAOYAL
Properties
Chemical formula	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 (pK_a)	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). N verify (what is ^YN ?) Infobox references

Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate baseofcis-aconitic acid, cis-aconitate is an intermediate in the isomerizationofcitratetoisocitrate 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:^[4]

(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.^[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]

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.

^ Pfendt, L.; Dražić, B.; Popović, G.; Drakulić, B.; Vitnik, Ž; Juranić, I. (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. 2003: 247–248. doi:10.3184/030823403103173732.

^ 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.

^ Zhang, Kou-Lin; Zhou, Fang; Yuan, Li-Min; Diao, Guo-Wang; Ng, Seik Weng (2009). "Synthesis and characterization of a novel photoluminescent three-dimensional metal–organic framework". Inorganica Chimica Acta. 362 (7): 2510–2514. doi:10.1016/j.ica.2008.10.008.

Citric acid cycle metabolic pathway

Acetyl-CoA + H₂O	Oxaloacetate NADH +H⁺ NAD⁺ Malate H₂O Fumarate FADH₂ FAD Succinate CoA + ATP (GTP) P_i + ADP (GDP) Succinyl-CoA
		NADH + H⁺ + CO₂
CoA		NAD⁺
	Citrate H₂O cis-Aconitate H₂O Isocitrate NAD(P)⁺ NAD(P)H + H⁺ Oxalosuccinate CO₂ 2-oxoglutarate