Alizarin glucoside

Rubia tinctorum roots Alizarin, alizarin glucoside, purpurin, pseudopurpurin, lucidin glucoside, lucidin primeveroside, munjistin, ruberythric acid EtOH/H20, H2S04 A ACN B ammonium formate/FA with EDTA 250, 254 nm/ESI (+) Post column modification of eluent (5% NH3 in H20) for NI mode... 

Fig. 2.148. UV (254 nm) profile of an acidic hydrolysate of an aqueous alcoholic extract of Rubia tinctorum (after 30 min). The mass spectra (sinlge MS) obtained with NI-ESI with ammonia added post-column and the UV-Vis spectra of peaks 3 and 4 are depicted, lucidin primeveroside (1), rubery-thic acid (2), lucidin glucoside (3), alizarin glucoside (4), munjistin (6), alizarin (8), and purpurin (9). Reprinted with permission from G. C. H. Derksen et al. [320].

Alizarin or l 2-dihydroxyanthraquinone is one of the most important dyes. Like indigo, the dye occurs in the plant (the madder root) as the glucoside of the leuco-compound. The cultivation of the madder plant, which, chiefly in southern France, extended over large areas, was brought to an end by the synthesis of the dye from the anthracene of coal-tar (Graebe and Liebennann, 1869). By distillation with zinc dust according to the method of Baeyer, these two chemists had previously obtained anthracene from alizarin. 

Morinda citrifolia L. M. officinalis L. Je Shu Ba Ji Tian (root) Dihydroxy methyl anthraquinone, glucoside morindin, rubichloric acid, alizarin, alpha-methyl ether, rubiadin-I-methyl ether, tannins, morindadiol, masperuloside, soranjudiol, nordamnacanthal.50-424 Treat beri-beri, cancer, lumbago, cholecystitis, increase leukocyte count, stimulate endocrine system. 

Turkey Red.—Alizarin is the chief constituent of the coloring matter Turkey red, which has been known since ancient times and which was obtained from the root of the madder plant, Rubia tinctorum L. The substance is of special interest because the determination of its constitution was one of the early triumphs of organic chemistry and because it was the first natural dye to be synthetically prepared. The name is derived from the oriental name for the madder, viz., alizari. In the madder root it is present as a glucoside known as ruberythric acid, which, on hydrolysis by fermentation or by boiling with acids, yields glucose and alizarin. Alizarin is a solid which sublimes as orange red needles, m.p. 289°, insoluble in water but slightly soluble in alcohol. 

Alizarin is one of the few natural dyestuffs which have been prepared synthetically, and is probably the only one which is prepared artificially on the large scale. It occurs generally as a glucoside, ruberythric acid CggH gOu [1, 2] in madder, the root of Rubia tincforium, and also in some other plants. 

Purpurin occurs with alizarin in the madder root [20], probably also as glucoside. It may be obtained artificially from alizarin by heating with manganese dioxide and sulphuric acid [21], or arsenic acid and also by melting an alizarinsulphonic acid (the so-called alizarin purpursulphonic acid) with potash... 

Derivation Occurs as a glucoside in madder root. Made synthetically by oxidation of alizarin. 

The presence of these glucosides along with the ruberythric acid in madder is the probable explanation for the well-known color difference between the natural and the synthetic alizarin. 

Galium spp. G. verum L. Rubiaceae Ladies bedstraw Psendopurpurin 2-hydroxyanthraquinone, alizarin-1-methyl ether, alizarin, xanthopurpurin, rubiadin, purpurin, lucidin 2-methoxyanthraquinone and others Schweppe Winter (1997) G. mollugo also contains apigenin and luteolin glucosides... 

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