| Revision as of 16:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456367549 of page 1,4-Dihydroxyanthraquinone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:59, 12 September 2024 edit 98.193.42.97 (talk) →Production: Text with editorialising added without citation. |
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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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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 456365801 |
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| verifiedrevid = 477206231 |
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| ImageFile = Quinizarin.svg |
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| ImageFile = Quinizarin.svg |
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| ImageSize = 190px |
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| ImageSize = 190px |
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| ImageSize1 = 210px |
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| ImageSize1 = 210px |
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| ImageName1 = Ball-and-stick model |
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| ImageName1 = Ball-and-stick model |
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| IUPACName = 1,4-dihydroxyanthracene-9,10-dione |
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| PIN = 1,4-Dihydroxyanthracene-9,10-dione |
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| OtherNames = Quinizarin; Solvent Orange 86 |
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| OtherNames = Quinizarin; Solvent Orange 86 |
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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_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H |
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| InChI = 1/C14H8O4/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,15-16H |
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| InChIKey = GUEIZVNYDFNHJU-UHFFFAOYAX |
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| InChIKey = GUEIZVNYDFNHJU-UHFFFAOYAX |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 17594 |
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| ChEMBL = 17594 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 81-64-1 |
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| CASNo = 81-64-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 8S496ZV3CS |
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| PubChem = 6688 |
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| PubChem = 6688 |
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| SMILES = O=C2c1ccccc1C(=O)c3c2c(O)ccc3O |
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| SMILES = O=C2c1ccccc1C(=O)c3c2c(O)ccc3O |
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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>14</sub>H<sub>8</sub>O<sub>4</sub> |
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| Formula = C<sub>14</sub>H<sub>8</sub>O<sub>4</sub> |
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| MolarMass = 240.21 g/mol |
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| MolarMass = 240.21 g/mol |
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| Appearance = Orange or red-brown crystalline powder |
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| Appearance = Orange or red-brown crystalline powder |
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| Density = |
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| Density = |
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| MeltingPtC = 198 to 199 |
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| MeltingPt = 198–199 °C |
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| BoilingPt = 450 °C |
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| BoilingPtC = 450 |
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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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| Autoignition = }} |
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}} |
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}} |
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'''1,4-Dihydroxyanthraquinone''', also called '''quinizarin''' or '''Solvent Orange 86''', is an ] derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from ] by replacement of two ] atoms by ] (OH) groups. It is one of ten ] isomers and occurs in small amounts (as a ]) in the root of the ] plant, '']''.<ref name=derk>{{ cite journal |author1=Derksen, G. C. H. |author2=Niederländer, H. A. G. |author3=van Beek, T. A. | title = Analysis of Anthraquinones in ''Rubia tinctorum'' L. by Liquid Chromatography Coupled with Diode-Array UV and Mass Spectrometric Detection | journal = Journal of Chromatography A | year = 2002 | volume = 978 | issue = 1–2 | pages = 119–127 | doi = 10.1016/S0021-9673(02)01412-7 |pmid=12458949 }}</ref> |
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==Production== |
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Quinizarin is produced by the reaction of ] and ] followed by hydrolysis of the chloride:<ref name=Ullmann>{{ Ullmann | author = Bien, H.-S. | author2 = Stawitz, J. | author3 = Wunderlich, K. | title = Anthraquinone Dyes and Intermediates | doi = 10.1002/14356007.a02_355 }}</ref><ref>{{cite journal|journal=Org. Synth.|year=1926|volume=6|page=78|doi=10.15227/orgsyn.006.0078|title=Quinizarin|first1=L. A.|last1=Bigelow|first2=H. H.|last2=Reynolds}}</ref> |
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It can also be prepared less efficiently from ] and ].{{fact|date = September 2024}} |
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==Uses== |
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Quinizarin is an inexpensive dye that is used to colour ] and some ]s. It is used as an intermediate for the synthesis of ]- and ]-derived dyes. The OH groups can be replaced by chloride. ] and ] afford other dyes. Amination (replacement of one OH by ArNH) with ] derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form ]s with ], ], and ].<ref name=Ullmann/> |
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]).]] |
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==See also== |
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*] |
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*] (alizarin) |
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*] (purpuroxanthin) |
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*] |
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*] (1,2,5,8-tetrahydroxyanthraquinone) |
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==References== |
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{{Reflist}} |
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{{anthraquinone}} |
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{{DEFAULTSORT:Dihydroxyanthraquinone, 1,4-}} |
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] |
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] |
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] |
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] |