| Revision as of 20:01, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 444684455 of page Aconitic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:38, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fixes |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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| Verifiedfields = changed |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443367538 |
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| verifiedrevid = 477240926 |
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| Name = ''cis''-Aconitic acid <small>(top)</small> and ''trans''-Aconitic acid <small>(bottom)</small> |
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| Name = Aconitic acid |
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| ImageFile1 = Cis-aconitic acid.png |
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| ImageFile1 = Cis-aconitic acid.png |
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| ImageClass1 = skin-invert |
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| ImageSize1 = 200px |
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| ImageSize1 = |
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| ImageName1 = ''cis''-Aconitic acid |
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| ImageCaption1 = ''cis''-aconitic acid |
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| ImageFile2 = Trans-aconitic acid.png |
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| ImageFile2 = Trans-aconitic acid.png |
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| ImageClass2 = skin-invert |
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| ImageSize2 = 200px |
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| ImageSize2 = |
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| ImageName2 = ''trans''-Aconitic acid |
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| ImageCaption2 = ''trans''-aconitic acid |
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| IUPACName = Prop-1-ene-1,2,3-tricarboxylic acid |
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| PIN = Prop-1-ene-1,2,3-tricarboxylic acid |
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| OtherNames = Achilleic acid; Equisetic acid; Citridinic acid; Pyrocitric acid |
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| OtherNames = Achilleic acid; equisetic acid; citridinic acid; pyrocitric acid; achilleaic acid; acinitic acid |
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| Reference = <ref>, ]</ref> |
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| Reference = <ref>{{ cite web | url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=309 | title = Aconitic Acid - Compound Summary (CID 309) | publisher = ] }}</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 303 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 93371T1BXP |
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| 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) |
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| 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) |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H8/c1-3-4-2/h3-4H,1-2H3 |
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| InChIKey = GTZCVFVGUGFEME-UHFFFAOYAL |
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| InChIKey = GTZCVFVGUGFEME-UHFFFAOYAL |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = GTZCVFVGUGFEME-UHFFFAOYSA-N |
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| StdInChIKey = GTZCVFVGUGFEME-UHFFFAOYSA-N |
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| PubChem1 = 309 |
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| CASNo_Ref = {{cascite|$1|??}} |
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| PubChem1_Comment = (''cis'' and ''trans'') |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 303 |
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| ChemSpiderID1_Comment = (''cis'') |
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| SMILES1 = |
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| SMILES1_Comment = (''cis'') |
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| InChI1 = |
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| InChI1_Comment = (''cis'') |
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| InChIKey1 = |
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| InChI3 = |
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| InChI3_Comment = (''cis'') |
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| InChIKey3 = |
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| PubChem2 = |
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| PubChem2_Comment = (''trans'') |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2 = |
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| ChemSpiderID2_Comment = (''trans'') |
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| SMILES2 = |
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| SMILES2_Comment = (''trans'') |
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| InChI2 = |
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| InChI2_Comment = (''trans'') |
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| InChIKey2 = |
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| InChI4 = |
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| InChI4_Comment = (''trans'') |
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| InChIKey4 = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 93371T1BXP |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = OF5471ZHRR |
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| UNII1_Comment = (''cis'') |
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| UNII2 = 7DB37960CW |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2_Comment = (''trans'') |
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| SMILES = |
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| CASNo = 499-12-7 |
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| CASNo = 499-12-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 309 |
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| CASNo1 = 585-84-2 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo1_Comment = (''cis'') |
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| ChEBI = 22211 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| SMILES = O=C(O)CC(=CC(=O)O)C(=O)O |
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| MeSHName = Aconitate |
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| CASNo2 = 4023-65-8 |
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| CASNo2_Comment = (''trans'') |
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}} |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| Section2 = {{Chembox Properties |
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| EC_number = |
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| C=6|H=6|O=6 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance = Colorless crystals |
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| Density = |
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| ChemSpiderID = |
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| RTECS = |
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| MeltingPt = 190 °C (decomp) (''trans isomer''), 122 °C (''cis isomer'') |
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| BoilingPt = |
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| pKa = 2.80, 4.46 (''trans isomer'') <ref> Dawson, R. M. C., et al., ''Data for Biochemical Research''', Oxford, Clarendon Press, 1959. </ref> |
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}} |
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}} |
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| Section3 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| Solubility = water |
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| C=6 | H=6 | O=6 |
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| Appearance = Colorless crystals |
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| MainHazards = |
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| FlashPt = |
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| Density = |
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| Autoignition = |
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| MeltingPtC = 190 |
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| MeltingPt_notes = (decomposes) (mixed isomers), 173 °C (''cis and trans isomers'') |
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| BoilingPt = |
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| pKa = 2.80, 4.46 (''trans isomer'')<ref>{{ cite book |author1=Dawson, R. M. C. |author2=Elliott, D. C. |author3=Elliott, W. H. | title = Data for Biochemical Research | edition = 3rd | location = Oxford | publisher = Clarendon Press | year = 1989 | isbn = 9780198552994 }}</ref> 2.78, 4.41, 6.21 (''cis isomer'')<ref>{{ cite journal |author1=Pfendt, L. |author2=Dražić, B. |author3= Popović, G. |author4=Drakulić, B. |author5=Vitnik, Ž |author6=Juranić, I. |title=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=Journal of Chemical Research |year=2003 |volume=2003 |issue=5 |pages=247–248 |doi=10.3184/030823403103173732}}</ref> |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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'''Aconitic acid''' refers to ]s with the formula {{chem2|HO2CCH2C(CO2H)\dCHCO2H}}. A white solid, it is clasified as a tricarboxylic acid. The two ] are ''cis''-aconitic acid and ''trans''-aconitic acid. The ] of ''cis''-aconitic acid, ''cis''-'''aconitate''' is an intermediate in the ]ization of ] to ] in the ]. It is acted upon by the enzyme ]. |
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Aconitic acid can be synthesized by dehydration of ] using ]:<ref>{{cite journal| author = Bruce, W. F. | title = Aconitic Acid | journal = Organic Syntheses | year = 1937 | volume = 17 | pages = 1|doi=10.15227/orgsyn.017.0001 }}</ref> |
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:(HO<sub>2</sub>CCH<sub>2</sub>)<sub>2</sub>C(OH)CO<sub>2</sub>H → HO<sub>2</sub>CCH=C(CO<sub>2</sub>H)CH<sub>2</sub>CO<sub>2</sub>H + H<sub>2</sub>O |
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A mixture of isomers are generated in this way. |
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Aconitic acid was originally isolated from '']'' by Swiss chemist and apothecary ] in 1820.<ref>{{cite book |last1=Brande |first1=William Thomas |title=A Manual of Chemistry, Vol II. |date=1848 |publisher=John W. Parker. |location=London |page=1344 |edition=6 |url=https://books.google.com/books?id=yyKxJYbsZgQC&dq=%22aconitic+acid%22&pg=PA1344 |access-date=8 November 2023}}</ref><ref>{{cite book |last1=Reichenbach |first1=Karl-Rudolf |title=Jacques Peschier (1769-1832): Ein Genfer Apotheker und Chemiker |date=2001 |publisher=Wissenschaftliche Verlagsgesellschaft mbH Stuttgart |location=Zürich |isbn=3804719090 |url=https://wellcomecollection.org/works/vjxjm7jj |access-date=8 November 2023}}</ref> It was first prepared by thermal dehydration.<ref>{{ cite journal | author = Pawolleck, B. | title = Substitutionsproducte der Citronensäure und ein Versuch zur Synthese der letzteren |trans-title=Substitution products of citric acid and an attempt at the synthesis of the latter | journal = Justus Liebig's Annalen der Chemie | year = 1875 | volume = 178 | issue = 2–3 | pages = 150–170 | url = https://babel.hathitrust.org/cgi/pt?id=mdp.39015026321573;view=1up;seq=554 | doi = 10.1002/jlac.18751780203 }}</ref> |
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Like the conjugate bases of other ], acotinic acid forms a variety of ]es. One example is the ] <sub>n</sub>.<ref>{{cite journal |doi=10.1016/j.ica.2008.10.008 |title=Synthesis and characterization of a novel photoluminescent three-dimensional metal–organic framework |date=2009 |last1=Zhang |first1=Kou-Lin |last2=Zhou |first2=Fang |last3=Yuan |first3=Li-Min |last4=Diao |first4=Guo-Wang |last5=Ng |first5=Seik Weng |journal=Inorganica Chimica Acta |volume=362 |issue=7 |pages=2510–2514 }}</ref> |
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==References== |
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{{reflist}} |
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{{Citric acid cycle}} |
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] |
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] |