1,2,3-trihydroxy-9,10-anthraquinone

Structural formula
General
Surname	1,2,3-trihydroxy-9,10-anthraquinone
other names	Anthracite brown Anthragallol 1,2,3-trihydroxyanthracene-9,10-dione 1,2,3-trioxyanthraquinone CI Mordant Brown 42 CI 58200
Molecular formula	C 14 H 8 O 5
External identifiers / databases
CAS number 602-64-2 EC number 210-022-4 ECHA InfoCard 100.009.112 PubChem 11768 ChemSpider 11275 Wikidata Q5413057
properties
Molar mass	256.21 g mol −1
Physical state	firmly
Melting point	315 ° C
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2,3-Trihydroxy-9,10-anthraquinone , also called anthracene brown or anthragallol , is a brown dye that belongs to the class of anthraquinone dyes .

Occurrence

1,2,3-Trihydroxy-9,10-anthraquinone occurs naturally in the roots of the madder ( Rubia tinctorum ) as a glycoside .

synthesis

1,2,3-trihydroxy-9,10-anthraquinone can be prepared by condensation of benzoic acid with gallic acid in the presence of concentrated sulfuric acid are prepared. Anthracene brown can also be obtained by Friedel-Crafts acylation of phthalic acid and 1,2,3-trihydroxybenzene in the presence of aluminum trichloride or tin salt.

properties

1,2,3-Trihydroxy-9,10-anthraquinone is a crystalline, brown, water-insoluble dye. It dissolves in alcohol and glacial acetic acid with a brownish-yellow color and in concentrated sulfuric acid with a brownish-red color. There are various details about the melting point in the literature. The information given by various authors is in the range between 313 and 315 ° C. Lower observed melting points at 310 ° C may result from more impure samples.

use

1,2,3-Trihydroxy-9,10-anthraquinone is used as the realest brown stain dye , for dyeing and printing wool and cotton .

Individual evidence

1. ↑ ^{a b} Tadataka Noro et al: Inhibition of Xanthine Oxidase by Anthraquinones . In: Chemical & Pharmaceutical Bulletin . tape 35 , no. 10 , 1987, pp. 4314-4316 , doi : 10.1248 / cpb.35.4314 .
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ^ ^{A b} Nicholas Eastaugh, Valentine Walsh, Tracey Chaplin, Ruth Siddall: Pigment Compendium: A Dictionary and Optical Microscopy of Historic Pigments . Routledge, 2008, ISBN 0-7506-8980-3 , pp. 21 ( limited preview in Google Book search).
4. ↑ C. Seuberlich: Effect of sulfuric acid on a mixture of gallic and benzoic acid . In: Reports of the German Chemical Society . tape 10 , no. 1 , 1877, p. 38-43 , doi : 10.1002 / cber.18770100114 .
5. ↑ Mugunthu R. Dhananjeyan, Youli P. Milev, Michael A. Kron, Muraleedharan G. Nair: Synthesis and Activity of Substituted Anthraquinones against a human filarial parasite, Brugia malayi . In: Journal of Medicinal Chemistry . tape 48 , no. 8 , 2005, p. 2822-2830 , doi : 10.1021 / jm0492655 .
6. ↑ LA Wiles: 249. The polarographic reduction of hydroxy and methoxyanthraquinones . In: Journal of the Chemical Society (Resumed) . ° C, 1952, p. 1358-1362 , doi : 10.1039 / JR9520001358 .
7. ↑ G. Flumiani, V. Bajić: Reviews of syntheses of Oxyanthrachinonsalzen . In: Monthly books for chemistry and related parts of other sciences . tape 71 , no. 1 , 1937, p. 293-297 , doi : 10.1007 / BF01798096 .
8. ↑ WD Treadwell, Gerold Schwarzenbach: About the electrometric titration of phenols in alcoholic solution . In: Helvetica Chimica Acta . tape 11 , no. 1 , 1928, pp. 386-405 , doi : 10.1002 / hlca.19280110148 .
9. ↑ Data sheet 1,2,3-trihydroxy-9,10-anthraquinone from AlfaAesar, accessed on January 6, 2013 ( PDF )(JavaScript required) .
10. ↑ Ernst L. Cahn: About Methylanthragallole . In: Reports of the German Chemical Society . tape 19 , no. 2 , 1886, p. 2333-2336 , doi : 10.1002 / cber.188601902152 .