Dihydroxyanthraquinones

The dihydroxyanthraquinones (formerly dioxyanthraquinones, dihydroxyanthrecen-9,10-diones according to IUPAC ) are constitutional isomers of anthraquinone in which two hydrogen atoms have been replaced by hydroxyl groups . They all have the molecular formula C ₁₄ H ₈ O ₄ .

All dihydroxyanthraquinones are soluble in alkaline solutions and in sulfuric acid . If boric acid is added to the sulfuric acid solution, a color change occurs through which the different dihydroxyanthraquinones can be recognized. The dihydroxyanthraquinones which have a hydroxyl group in position 2 also have the property that hydrogen easily replaces them by reduction.

List of existing dihydroxyanthraquinones

There are a total of 28 different dihydroxyanthraquinones, but due to the symmetry of the anthraquinone, only 10 different isomers remain.

1,2-dihydroxyanthraquinone ,
also alizarin
1,3-dihydroxyanthraquinone ,
also xanthopurpurine
1,4-dihydroxyanthraquinone ,
also quinizarine
1,5-dihydroxyanthraquinone ,
also anthrarufin
1,6-Dihydroxyanthraquinone ,
also the highest dioxyanthraquinone
1,7-dihydroxyanthraquinone ,
also m -dihydroxyanthraquinone
1,8-dihydroxyanthraquinone ,
also chrysazine
2,3-dihydroxyanthraquinone ,
also hystazarin
2,6-dihydroxyanthraquinone ,
also anthraflavic acid
2,7-dihydroxyanthraquinone ,
also isoanthraflavic acid

Web links

Commons : Dihydroxyanthraquinones - Collection of Images, Videos, and Audio Files

Individual evidence

↑ A. Conranesco: Anthraquinone derivatives . In: Anthony Standen (Ed.): Kirk-Othmer Encyclopedia of Chemical Technology . tape 2 . Interscience Publishers, New York 1966, ISBN 0-470-48347-4 , pp. 467 .
^ Rudolf Bauer, Heinrich Wieland: Reduction and hydrogenation of organic compounds . Springer-Verlag, 1918, ISBN 978-3-662-33872-8 , p. 56 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g Andre Wahl, FW Atack: The Manufacture Of Organic Dyestuffs . G. Bell and Sons, Limited. 1919. Retrieved June 26, 2017.
↑ J. Winkler, W. Jenny: To the knowledge of the BOHN-SCHMIDT'schen reaction. 1st communication. Isolation and structure elucidation of novel compounds from the oleum melt of α-hydroxyanthraquinones , In: Helvetica Chimica Acta , Volume 48, No. 1, 1965, pp. 119-126, doi : 10.1002 / hlca.19650480112 .
↑ O. Frobenius, E. Hepp: About the 1.6-Dioxy-anthraquinone. In: Reports of the German Chemical Society . 40, 1907, pp. 1048-1051, doi : 10.1002 / cber.190704001157 .
↑ Entry on hystazarin. In: Römpp Online . Georg Thieme Verlag, accessed on August 4, 2018.

[Kirk-Othmer-1] A. Conranesco: Anthraquinone derivatives . In: Anthony Standen (Ed.): Kirk-Othmer Encyclopedia of Chemical Technology . tape 2 . Interscience Publishers, New York 1966, ISBN 0-470-48347-4 , pp. 467 .

[Bauer_Wieland-2] Rudolf Bauer, Heinrich Wieland: Reduction and hydrogenation of organic compounds . Springer-Verlag, 1918, ISBN 978-3-662-33872-8 , p. 56 ( limited preview in Google Book search).

[Manufacture-3] ↑ ^a ^b ^c ^d ^e ^f ^g Andre Wahl, FW Atack: The Manufacture Of Organic Dyestuffs . G. Bell and Sons, Limited. 1919. Retrieved June 26, 2017.

[Helvetica-4] J. Winkler, W. Jenny: To the knowledge of the BOHN-SCHMIDT'schen reaction. 1st communication. Isolation and structure elucidation of novel compounds from the oleum melt of α-hydroxyanthraquinones , In: Helvetica Chimica Acta , Volume 48, No. 1, 1965, pp. 119-126, doi : 10.1002 / hlca.19650480112 .

[Frobenius-5] O. Frobenius, E. Hepp: About the 1.6-Dioxy-anthraquinone. In: Reports of the German Chemical Society . 40, 1907, pp. 1048-1051, doi : 10.1002 / cber.190704001157 .

[Römpp1-6] Entry on hystazarin. In: Römpp Online . Georg Thieme Verlag, accessed on August 4, 2018.