| Revision as of 12:52, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 472936364 of page Gentisic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 18:01, 4 January 2024 edit OAbot (talk | contribs)Bots442,978 editsm Open access bot: pmc updated in citation with #oabot. |
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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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|Watchedfields = changed |
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| verifiedrevid = 443834051 |
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|verifiedrevid = 476997017 |
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|ImageFile=Gentisinsäure.svg |
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|ImageFile =Gentisinsäure.svg |
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|ImageSize= |
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|ImageSize = 150 |
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|IUPACName=2,5-dihydroxybenzoic acid |
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|ImageAlt = Skeletal formula of gentisic acid |
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|OtherNames=DHB<br>2,5-dihydroxybenzoic acid<br>5-Hydroxysalicylic acid<br>Gentianic acid<br>Carboxyhydroquinone<br>2,5-Dioxybenzoic Acid<br>Hydroquinonecarboxylic acid |
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|ImageFile1 = Gentisic acid 3D spacefill.png |
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|Reference=<ref>, ].</ref> |
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|ImageSize1 = 150 |
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|Section1= {{Chembox Identifiers |
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|ImageAlt1 = Space-filling model of the gentisic acid molecule |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PIN =2,5-Dihydroxybenzoic acid |
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| ChemSpiderID = 3350 |
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|OtherNames =DHB<br>5-Hydroxysalicylic acid<br>Gentianic acid<br>Carboxyhydroquinone<br>2,5-Dioxybenzoic Acid<br>Hydroquinonecarboxylic acid |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|Reference =<ref>, ].</ref> |
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| UNII = VP36V95O3T |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG = C00628 |
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|ChemSpiderID = 3350 |
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| InChI = 1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| InChIKey = WXTMDXOMEHJXQO-UHFFFAOYAO |
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|UNII = VP36V95O3T |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEMBL = 1461 |
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|KEGG = C00628 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
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|InChI = 1/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
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|InChIKey = WXTMDXOMEHJXQO-UHFFFAOYAO |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChIKey = WXTMDXOMEHJXQO-UHFFFAOYSA-N |
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|ChEMBL = 1461 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo=490-79-9 |
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|StdInChI = 1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
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| PubChem=3469 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = WXTMDXOMEHJXQO-UHFFFAOYSA-N |
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| ChEBI = 17189 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = O=C(O)c1cc(O)ccc1O |
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|CASNo =490-79-9 |
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|PubChem =3469 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 17189 |
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|SMILES = O=C(O)c1cc(O)ccc1O |
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}} |
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}} |
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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>6</sub>O<sub>4</sub> |
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|Formula = C<sub>7</sub>H<sub>6</sub>O<sub>4</sub> |
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| MolarMass = 154.12 g/mol |
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|MolarMass = 154.12 g/mol |
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| Appearance = white to yellow powder |
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|Appearance = white to yellow powder |
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|MeltingPtC = 204 |
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| Density = |
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| MeltingPt_ref=<ref name=crc>Haynes, p. 3.190</ref> |
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| MeltingPt = 200 - 205 C (Sublimes) |
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| pKa = 2.97<ref>Haynes, p. 5.91</ref> |
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| BoilingPt = |
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| Solubility = |
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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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| Autoignition= |
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}} |
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}} |
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}} |
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}} |
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'''Gentisic acid''' is a ]. It is a derivative of ] and a minor (1%) product of the metabolic break down of ], excreted by the kidneys.<ref>{{cite journal|doi=10.1056/NEJM197208312870903|title=Salicylate accumulation kinetics in man|journal=New England Journal of Medicine|date=1972-08-31|first=G|last=Levy|author2=Tsuchiya, T|volume=287|issue=9|pages=430–2|pmid=5044917 }}</ref> |
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It is also found in the African tree '']'' and in ].<ref>{{cite journal|doi=10.3390/molecules14020827 |doi-access=free |title=Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times |date=2009 |last1=Tian |first1=Rong-Rong |last2=Pan |first2=Qiu-Hong |last3=Zhan |first3=Ji-Cheng |last4=Li |first4=Jing-Ming |last5=Wan |first5=Si-Bao |last6=Zhang |first6=Qing-Hua |last7=Huang |first7=Wei-Dong |journal=Molecules |volume=14 |issue=2 |pages=827–838 |pmc=6253884 }}</ref> |
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== Production == |
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Gentisic acid is produced by carboxylation of ].<ref name=Ullmann>Hudnall, Phillip M. (2005) "Hydroquinone" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a13_499}}.</ref> |
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:C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub> + CO<sub>2</sub> → C<sub>6</sub>H<sub>3</sub>(CO<sub>2</sub>H)(OH)<sub>2</sub> |
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This conversion is an example of a ]. |
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Alternatively the compound can be synthesized from ] via ].<ref>{{cite book|last=Behrman|first=E.J.|title=Organic Reactions, Volume 35|date=1988|publisher=John Wiley & Sons Inc.|location=New York|isbn=978-0471832539|page=440|url=https://books.google.com/books?id=sfjdPwAACAAJ&q=0471832537}}</ref><ref>{{cite journal|author1=Schock, R. U. Jr. |author2=Tabern, D. L. |title=The Persulfate Oxidation of Salicylic Acid. 2,3,5-Trihydroxybenzoic Acid|journal=The Journal of Organic Chemistry|date=1951|volume=16|issue=11|pages=1772–1775|doi=10.1021/jo50005a018}}<!--|access-date=15 May 2014--></ref> |
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==Reactions== |
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In the presence of the enzyme ], gentisic acid reacts with ] to give ]: |
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:2,5-dihydroxybenzoate + O<sub>2</sub> <math>\rightleftharpoons</math> maleylpyruvate |
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== Applications == |
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As a ], gentisic acid is readily oxidised and is used as an ] ] in some ] preparations. |
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In the laboratory, it is used as a sample matrix in ] (MALDI) ],<ref>{{cite journal |vauthors=Strupat K, Karas M, Hillenkamp F |title=2,5-Dihidroxybenzoic acid: a new matrix for laser desorption-ionization mass spectrometry |journal=Int. J. Mass Spectrom. Ion Process. |volume=72 |issue=111 |pages=89–102 |year=1991 |doi=10.1016/0168-1176(91)85050-V |bibcode=1991IJMSI.111...89S}}</ref> and has been shown to conveniently detect peptides incorporating the boronic acid moiety by MALDI.<ref>{{cite journal|last=Crumpton|first=J.|author2=Zhang, W. |author3=Santos, W. L. |title=Facile Analysis and Sequencing of Linear and Branched Peptide Boronic Acids by MALDI Mass Spectrometry|journal=Analytical Chemistry|year=2011|volume=83|issue=9|pages=3548–3554|doi=10.1021/ac2002565|pmid=21449540|pmc=3090651}}</ref> |
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== References == |
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{{reflist}} |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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{{Phenolic acid}} |
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{{DEFAULTSORT:Gentisic Acid}} |
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] |
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] |
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] |
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] |
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] |