1,4-Dihydroxyanthraquinone

changed 477206231 Quinizarin.svg 190px Skeletal formula Quinizarin-3D-balls.png 210px Ball-and-stick model 1,4-Dihydroxyanthracene-9,10-dione Quinizarin; Solvent Orange 86 correct chemspider correct EBI 37487 6433 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 GUEIZVNYDFNHJU-UHFFFAOYAX correct EBI 17594 correct chemspider 1S/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 correct chemspider GUEIZVNYDFNHJU-UHFFFAOYSA-N correct CAS 81-64-1 correct FDA 8S496ZV3CS 6688 O=C2c1ccccc1C(=O)c3c2c(O)ccc3O C14H8O4 240.21 g/mol Orange or red-brown crystalline powder 198 to 199 450 1,4-Dihydroxyanthraquinone, also called quinizarin or Solvent Orange 86, is a chromogenic organic compound derived from anthroquinone. Quinizarin is an orange or red-brown crystalline powder. It is formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxyl (OH) groups. It is one of ten dihydroxyanthraquinone isomers and occurs in small amounts (as a glycoside) in the root of the madder plant, Rubia tinctorum.Derksen, G. C. H. Niederländer, H. A. G. van Beek, T. A. Analysis of Anthraquinones in Rubia tinctorum L. by Liquid Chromatography Coupled with Diode-Array UV and Mass Spectrometric Detection Journal of Chromatography A 2002 978 1–2 119–127 10.1016/S0021-9673(02)01412-7 12458949 2002JChA..978..119D https://research.wur.nl/en/publications/analysis-of-anthraquinones-in-rubia-tinctorum-l-by-liquid-chromat Production Quinizarin is produced by the reaction of phthalic anhydride and 4-chlorophenol followed by hydrolysis of the chloride: Bien, H.-S. Stawitz, J. Wunderlich, K. Anthraquinone Dyes and Intermediates 10.1002/14356007.a02_355 Org. Synth. 1926 6 78 10.15227/orgsyn.006.0078 free Quinizarin L. A. Bigelow H. H. Reynolds thumb|center|444px|Summary equation for one synthesis of alizarin.[sic.] It can also be prepared less efficiently from phthalic anhydride and hydroquinone. September 2024 Uses Industrial Quinizarin is an inexpensive dye that is used to color gasoline and some heating oils. It is used as an intermediate for the synthesis of indanthrene- and alizarin-derived dyes. The OH groups can be replaced by chloride. Chlorination and bromination afford other dyes. Amination (replacement of one OH by ArNH) with aniline derivatives followed by sulfonation affords other dyes such as Acid Violet 43. It is also used to form lake pigments with calcium, barium, and lead. Analytical Chemistry In a dimethyl sulfoxide medium with the presence of sodium hydroxide and sodium carbonate, quinizarin reacts with lithium cations to produce a blue-violet color. This has been proposed as a method for the spectrophotometric determination of lithium in blood and human serum, as an alternative to the highly toxic organoarsenic reagent thorin.Gracia L January 1997 Spectrophotometric determination of lithium with Quinizarin in drugs and serum https://linkinghub.elsevier.com/retrieve/pii/S0039914096020188 Talanta 44 1 75–83 10.1016/S0039-9140(96)02018-8 18966719 0039-9140 subscription thumb|left|Quinizarin sample (Historic Dye Collection of TU Dresden). See also Hydroxyanthraquinone 1,2-Dihydroxyanthraquinone (alizarin) 1,3-Dihydroxyanthraquinone (purpuroxanthin) Trihydroxyanthraquinone Quinalizarin (1,2,5,8-tetrahydroxyanthraquinone) References Category:Anthraquinone dyes Category:Dihydroxyanthraquinones Category:Hydroquinones Category:3-Hydroxypropenals within hydroxyquinones