| Revision as of 16:16, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 469395630 of page Quinic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 03:00, 20 November 2024 edit 66.215.184.32 (talk) →Further reading: Flagged what appears to be a dead link. |
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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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{{chembox |
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{{chembox |
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| verifiedrevid = 464378657 |
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| verifiedrevid = 470455534 |
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| Name = Quinic acid |
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| ImageFileL1 = Quinic acid flat.svg |
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| Name = Quinic acid |
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| ImageFileL1 = Quinic acid flat.svg |
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| ImageNameL1 = Quinic acid |
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| ImageSizeL1 = 120px |
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| ImageFileR1 = (−)-quinic-acid-from-xtal-3D-bs-17.png |
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| ImageNameL1 = Quinic acid |
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| ImageFileR1 = Quinic-acid-3D-balls.png |
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| ImageNameR1 = Quinic acid |
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| PIN = (1''S'',3''R'',4''S'',5''R'')-1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid |
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| ImageSizeR1 = 120px |
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|Section1={{Chembox Identifiers |
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| ImageNameR1 = Quinic acid |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| IUPACName = (1''S'',3''R'',4''S'',5''R'')-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10246715 |
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| ChemSpiderID = 10246715 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 77-95-2 |
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| CASNo = 77-95-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 6508 |
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| UNII = 058C04BGYI |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem = 6508 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17521 |
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| ChEBI = 17521 |
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| SMILES = O1(C(O)(O)(O)C1)C(O)=O |
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| SMILES = O1(C(O)(O)(O)C1)C(O)=O |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>7</sub>H<sub>12</sub>O<sub>6</sub> |
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| Formula = C<sub>7</sub>H<sub>12</sub>O<sub>6</sub> |
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| MolarMass = 192.17 g/mol |
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| MolarMass = 192.17 g/mol |
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| Density = 1.35 g/cm<sup>3</sup> |
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| ExactMass = 192.063388 |
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| MeltingPtC = 168 |
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| Density = 1.35 g/cm³ |
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| BoilingPt = |
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| MeltingPtC = 168 |
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| BoilingPt = |
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|Section3={{Chembox Hazards |
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| NFPA-H = 0 |
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| NFPA-F = 0 |
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| NFPA-R = 0 |
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| GHSPictograms = {{GHS07}}<ref name=Sigma>{{Cite web |title=D-(−)-Quinic acid Safety Data Sheet |url=https://www.sigmaaldrich.com/DE/en/product/aldrich/138622 |website=]}}</ref> |
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| GHSSignalWord = Warning<ref name=Sigma/> |
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| HPhrases = {{H-phrases|319}}<ref name=Sigma/> |
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| PPhrases = {{P-phrases|264|280|305+351+338|337+313}}<ref name=Sigma/> |
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'''Quinic acid''' is a ], a cyclic polyol, and a ]. It is a colorless solid that can be extracted from plant sources. Quinic acid is implicated in the perceived acidity of coffee. |
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==Occurrence and preparation== |
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The compound is obtained from ], ], and the bark of '']''.<ref>{{Cite journal|pmid=21761864|doi=10.1021/jf201801q|title=Characterization of Phenolic Components in Polar Extracts of Eucalyptus globulus Labill. Bark by High-Performance Liquid Chromatography–Mass Spectrometry|year=2011|last1=Santos|first1=Sónia A. O.|last2=Freire|first2=Carmen S. R.|last3=Domingues|first3=M. Rosário M.|last4=Silvestre|first4=Armando J. D.|last5=Neto|first5=Carlos Pascoal|journal=Journal of Agricultural and Food Chemistry|volume=59|issue=17|pages=9386–93}}</ref> It is a constituent of the ]. |
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'']'', the European stinging nettle, is another common source.{{Citation needed|reason=nettles contain some chlorogenic acid, no free quinic acid to my knowledge|date=August 2024}} |
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It is made synthetically by ] of ]. Quinic acid is also implicated in the perceived acidity of coffee. |
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== History and biosynthesis == |
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], biosynthetic precursor to aromatic amino acids, is a close relative of quinic acid.]]This substance was isolated for the first time in 1790 by ] ] Friedrich Christian Hofmann in ] from ].<ref>Hofmann: ''Crell's chemische Annal.'' '''1790''', II, p. 314, cited in S. Baup: ''Über die Chinasäure und einige ihrer Verbindungen''. In: ''Annalen der Physik und Chemie'' '''1833''', p. 64–70 ({{Google books|hSEAAAAAMAAJ||page=64}}).</ref> Its transformation into ] by animal metabolism was studied by German chemist Eduard Lautemann in 1863.<ref>Lautemann, E. (1863) (On the reduction of quinic acid to benzoic acid and its transformation into hippuric acid in the animal organism), ''Annalen der Chemie'', '''125''' : 9–13.</ref> |
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Its ] begins with the transformation of glucose into ]. This four-carbon substrate is condensed with ] to give the seven-carbon ] by the action of a synthase. Two subsequent steps involving dehydroquinic acid synthase and a dehydrogenase afford the compound.<ref name=Barco>{{cite journal|title=D(-)-Quinic Acid: a Chiron Store for Natural Product Synthesis|author1=Barco, Achille |author2=Benetti, Simonetta |author3=De Risi, Carmela |author4=Marchetti, Paolo |author5=Pollini, Gian P. |author6=Zanirato, Vinicio |journal=Tetrahedron: Asymmetry|year=1997|volume=8|pages=3515–3545|doi=10.1016/S0957-4166(97)00471-0}}</ref> |
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Derived bicyclic ]s are called '''quinides'''. One example is ]. |
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] and oxidation of quinic acid affords ].<ref name=Barco/> |
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==Applications and medicinal activity== |
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Quinic acid is used as an ]. |
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This acid is a versatile chiral starting material for the synthesis of pharmaceuticals.<ref name=Barco/> It is a building block in the synthesis of ], which is used to treat ] and ]. |
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==References== |
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{{Reflist}} |
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==Further reading== |
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*{{cite web |title=Quinic acid - chiral compounds from nature - Buchler quinine plant in Braunschweig, Germany |work=Quinic acid |url=http://www.quinine-buchler.com/quinicacid.htm |access-date=September 5, 2005}}{{dead link|date=November 2024}} |
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*{{cite web |title=Quinic acid |work=Fast Health |url=http://www.fasthealth.com/dictionary/q/quinic_acid.php |access-date=September 5, 2005}} |
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*{{cite web |title=History of Xenobiotic Metabolism |url=http://www.issx.org/hisjune.html |access-date=September 5, 2005 |archive-url=https://web.archive.org/web/20050412074846/http://www.issx.org/hisjune.html <!-- Bot retrieved archive --> |archive-date=April 12, 2005}} |
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*{{cite AmCyc |wstitle=Kinic Acid}} |
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{{hydrolysable tannin}} |
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{{Authority control}} |
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{{DEFAULTSORT:Quinic Acid}} |
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] |
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] |