1,2,3-trihydroxy-9,10-anthraquinone
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Surname | 1,2,3-trihydroxy-9,10-anthraquinone | ||||||||||||||||||
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Molecular formula | C 14 H 8 O 5 | ||||||||||||||||||
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properties | |||||||||||||||||||
Molar mass | 256.21 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
315 ° C |
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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
- ↑ 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 .
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ^ 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).
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ↑ Data sheet 1,2,3-trihydroxy-9,10-anthraquinone from AlfaAesar, accessed on January 6, 2013 ( PDF )(JavaScript required) .
- ↑ 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 .