| Revision as of 17:49, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'UNII', 'ChEBI').← Previous edit |
Latest revision as of 15:28, 27 July 2022 edit undoCitation bot (talk | contribs)Bots5,419,151 edits Add: doi-access, authors 1-1. Removed proxy/dead URL that duplicated identifier. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by AManWithNoPlan | #UCB_CommandLine |
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{{Orphan|date=February 2009}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 414444322 |
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| verifiedrevid = 443715899 |
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| ImageFile = Duroquinone.png |
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| ImageFileL1 = Duroquinone.png |
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| ImageSize = 120px |
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| ImageSizeL1 = 105 |
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| IUPACName = 2,3,5,6-Tetramethyl-1,4-benzoquinone |
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| ImageAltL1 = Structural formula of duroquinone |
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| OtherNames = Tetramethyl-''p''-benzoquinone |
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| ImageFileR1 = Duroquinone 3D ball.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeR1 = 145 |
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| ImageAltR1 = Ball-and-stick model of the duroquinone molecule |
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| PIN = 2,3,5,6-Tetramethylcyclohexa-2,5-diene-1,4-dione |
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| OtherNames = 2,3,5,6-Tetramethyl-1,4-benzoquinone<br />Tetramethyl-''p''-benzoquinone |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 61539 |
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| ChemSpiderID = 61539 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 527-17-3 |
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| CASNo = 527-17-3 |
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| PubChem = |
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| PubChem = 68238 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01927 |
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| DrugBank = DB01927 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = X0Q8791R69 |
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| UNII = X0Q8791R69 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 42023 |
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| ChEBI = 42023 |
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| Beilstein = 1909128 |
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| Gmelin = 279610 |
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| EINECS = 208-409-8 |
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| SMILES = CC1=C(C(=O)C(=C(C1=O)C)C)C |
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| SMILES = CC1=C(C(=O)C(=C(C1=O)C)C)C |
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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>10</sub>H<sub>12</sub>O<sub>2</sub> |
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| Formula = C<sub>10</sub>H<sub>12</sub>O<sub>2</sub> |
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| MolarMass = 164.20408 g/mol |
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| MolarMass = 164.20408 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = |
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| Density = |
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| MeltingPt = 109 - 114 °C |
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| MeltingPtC = 109 to 114 |
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| MeltingPt_notes = |
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| BoilingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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'''Duroquinone''' is an organic ] (C<sub>6</sub>(CH<sub>3</sub>)<sub>4</sub>O<sub>2</sub>). It is related to ] by replacement of four H centres with methyl (Me) groups. The C<sub>10</sub>O<sub>2</sub> core of this molecule is planar with two pairs of C=O and C=C bonds.<ref name=Kochi>J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.{{doi|10.1021/ja066471o}}</ref> |
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'''Duroquinone''' is a derivative of ]. |
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The compound is produced via nitration of ] (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.<ref>{{OrgSynth|author=Lee Irvin Smith.|year=1943|title=Duronquinone|volume= |pages= |collvol=2|collvolpages=254|prep=CV2P0254}}</ref> |
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It is also used in the formation of a "]" (16 duroquinone molecules surrounding a 17th in the middle).<ref>*{{cite news |
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A derived ] (η<sup>2</sup>,η<sup>2</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>4</sub>O<sub>2</sub>)Fe(CO)<sub>3</sub> is obtained by the carbonylation of ] in the presence of ].<ref>H. W. Sternberg, R. Markby and I. Wender, "A Quinone Iron Tricarbonyl Complex and its Significance in Organic Synthesis", Journal of the American Chemical Society 1958 volume 80, pp. 1009-1010. {{doi|10.1021/ja01537a075}}</ref> |
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The molecule has been mentioned in the popular press as a component of a "nano brain".<ref>*{{cite news |
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| first = Jonathan |
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| first = Jonathan |
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| last = Fildes |
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| last = Fildes |
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| authorlink = |
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| author = |
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| author = |
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| coauthors = |
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| title = Chemical brain controls nanobots |
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| title = Chemical brain controls nanobots |
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| url = http://news.bbc.co.uk/1/hi/sci/tech/7288426.stm |
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| url = http://news.bbc.co.uk/1/hi/sci/tech/7288426.stm |
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}}</ref> |
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}}</ref> |
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Duroquinone was observed in a degradation products generated from pyrolysis of ].<ref>{{Cite journal |last1=Wu |first1=Dan |last2=O’Shea |first2=Donal F. |date=2020-03-24 |title=Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate |journal=Proceedings of the National Academy of Sciences |language=en |volume=117 |issue=12 |pages=6349–6355 |doi=10.1073/pnas.1920925117 |issn=0027-8424 |pmc=7104367 |pmid=32156732|doi-access=free }}</ref> |
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== References == |
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== References == |
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{{reflist}} |
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{{reflist}} |
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] |
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] |
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{{ketone-stub}} |
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{{ketone-stub}} |
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] |
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