| Revision as of 12:40, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chem← Previous edit |
Latest revision as of 09:21, 27 January 2018 edit undoEmeldir (talk | contribs)Extended confirmed users1,659 edits preferred IUPAC name (PIN) according to ''Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book)'' |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443862237 |
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| verifiedrevid = 443863608 |
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| ImageFileL1 = 2-hydroxy-1,4-benzoquinone.svg |
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| ImageFileL1 = 2-hydroxy-1,4-benzoquinone.svg |
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| ImageSizeL1 = 100px |
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| ImageFileR1 = Hydroxy-1,4-benzoquinone-3D-balls.png |
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| ImageFileR1 = Hydroxy-1,4-benzoquinone-3D-balls.png |
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| ImageSizeR1 = 140px |
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| ImageSizeR1 = 140px |
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| IUPACName = 2-hydroxycyclohexa-2,5-diene-1,4-dione |
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| PIN = 2-Hydroxycyclohexa-2,5-diene-1,4-dione |
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| OtherNames = 2-Hydroxy-p-benzoquinone |
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| OtherNames = 2-Hydroxy-''p''-benzoquinone |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 2474-72-8 |
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| CASNo = 2474-72-8 |
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| PubChem = 151011 |
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| PubChem = 151011 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 18400 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = C7I5HV2JFI |
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| UNII = C7I5HV2JFI |
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| SMILES = C1=CC(=O)C(=CC1=O)O }} |
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| SMILES = C1=CC(=O)C(=CC1=O)O |
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| ChemSpiderID = 133103 |
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| InChI = 1/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H |
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| InChIKey = GPLIMIJPIZGPIF-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C6H4O3/c7-4-1-2-5(8)6(9)3-4/h1-3,9H |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = GPLIMIJPIZGPIF-UHFFFAOYSA-N}} |
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| Formula = C<sub>6</sub>H<sub>4</sub>O<sub>3</sub> |
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| Formula = C<sub>6</sub>H<sub>4</sub>O<sub>3</sub> |
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| MolarMass = 124.1 g/mol |
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| MolarMass = 124.1 g/mol |
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The compound is often called '''2-hydroxy-1,4-benzoquinone''', but the "2-" prefix is superfluous since there is no other hydroxy derivative of 1,4-benzoquinone. The ] name is '''2-hydroxycyclohexa-2,5-diene-1,4-dione'''. |
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The compound is often called '''2-hydroxy-1,4-benzoquinone''', but the "2-" prefix is superfluous since there is no other hydroxy derivative of 1,4-benzoquinone. The ] name is '''2-hydroxycyclohexa-2,5-diene-1,4-dione'''. |
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It is formed by the reaction of 1,4-benzoquinone with hydrogen peroxide and is a byproduct of the metabolism of ]s, such as ].<ref name=bodo>{{cite journal | pmc = 107334 | pmid = 9658009 | year = 1998 | last1 = Philipp | first1 = B | last2 = Schink | first2 = B | title = Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius | volume = 180 | issue = 14 | pages = 3644–9 | journal = Journal of bacteriology }}</ref> The ] ] catalyzes the conversion of 1,2,4-benzenetriol to 2-hydroxy-1,4-benzoquinone, and the enzyme ] catalyzes the reverse reaction. The enzyme ] converts it to 1,4-benzoquinone. |
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It is formed by the reaction of 1,4-benzoquinone with hydrogen peroxide and is a byproduct of the metabolism of ]s, such as ].<ref name=bodo>{{cite journal | pmc = 107334 | pmid = 9658009 | year = 1998 | last1 = Philipp | first1 = B | last2 = Schink | first2 = B | title = Evidence of two oxidative reaction steps initiating anaerobic degradation of resorcinol (1,3-dihydroxybenzene) by the denitrifying bacterium Azoarcus anaerobius | volume = 180 | issue = 14 | pages = 3644–9 | journal = Journal of Bacteriology }}</ref> The ] ] catalyzes the conversion of 1,2,4-benzenetriol to 2-hydroxy-1,4-benzoquinone, and the enzyme ] catalyzes the reverse reaction. The enzyme ] converts it to 1,4-benzoquinone. |
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It tends to dimerize spontaneously by ] bridges.<ref name=bodo/> |
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It tends to dimerize spontaneously by ] bridges.<ref name=bodo/> |
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==See also== |
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==See also== |
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==References== |
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==References== |
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{{reflist}} |
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{{reflist}} |
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