Dihydroxy methyl anthraquinone

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. 

A-Dihydroxy-6-methyl-anthraquinone (XIII) Physcion (XV) Anthragallol (XVIII) Anthragallol-3-fflethyl ether (XX)... 

C16H3402 octytperoxide 7530-07-6 651 48 58.613 2 29951 C17H1405 1,3-dihydroxy-2-ethoxy methyl anthraquinone 17526-17-9 476.15 41.597 2... 

CAS 481-74-3 EINECS/ELINCS 205-572-2 Synonyms 9,10-Anthracenedione 1,8-dihydroxy-3-methyl- Anthraquinone, 1,8-dihydroxy-3-methyl- Chrysophanol Cl 75400 Cl natural yellow 23... 

Derivatives of diaminoanthrarufin (3.77 X = Y = H) and its 1,8-dihydroxy-4,5-diamino isomer (diaminochrysazin) have been among the most widely used anthraquinone dyes for ester fibres. For example, methylation of diaminoanthrarufin gives Cl Disperse Blue 26, a mixture of several components. Study of the pure N-alkylated derivatives from the base confirmed that monosubstitution (3.77 X = H, Y = alkyl) gives mid-blue dyes with excellent dyeing properties and acceptable fastness on polyester, but the bis-alkyl dyes (3.77 X = Y = alkyl) are greener and inferior in application properties. Mixtures of the unsubstituted base with alkylated components, as obtained industrially, were especially advantageous for build-up to heavy depths, however [93]. 

Further reduction of quinones - acquisition of four or more hydrogens per molecule - was achieved with lithium aluminum hydride which reduced, in yields lower than 10%, 2-methyl-1,4-naphthoquinone to 1,2,3,4-tetrahydro-l,4-dihydroxy-2-methylnaphthalene and to l,2,3,4-tetrahydro-4-hydroxy-l-keto-2-methylnaphthalene [931]. Lithium aluminum hydride [931], sodium borohydride, lithium trie thy Iborohydride and 9-borabicyclo[3.3.1Jnomine [100] converted anthraquinone to 9,10-dihydro-9,10-dihydroxyanthracene in respective yields of 67, 65, 77 and 79%. 

Preparation of nearly all important anthraquinones starts from the following key intermediates anthraquinonesulfonic acids, nitroanthraquinones, and the products of nucleus synthesis, 1,4-dihydroxy-, 2-methyl-, and 2-chloroanthraquinone. The only exceptions are derivatives with condensed rings, e.g., benzan-throne and derived products, which are prepared directly from anthraquinone via anthrone. 

XX Anthragallol-3-methyl ether — 1,2-Dihydroxy-3-methoxy-anthraquinone... 

Dihydroxy-2-methyl-9,10-anthraquinone (2-Methylchry- sdzin) 175 Diacetate, 205... 

Chrysophanol, l,8-dihydroxy-3-methyl-9,10-anthracenedione, an anthraquinone, occurs in the free state and as a glucoside in various plants, notably Aloe species and Rheum species. It is listed by many sources as synonymous with chrysophanic acid Merck Index, 1996 WHO, 1999) and is listed by the Colour Index (1971) as Cl 75400. 

Itokawa et al 74) reported the NMR spectra of some anthraquinones isolated from Rubia species. For one of the compounds a 2-methyl-1,3,6 (or 7)-trihydroxy-9,10-anthraquinone structure was assumed based on various spectral data. Eventually it was stated that the hydroxyl group was in the 6-position rather than in the 7-position because of a 0.6-0.8 ppm upfield shift observed for C-9 if compared with compounds having a 1,3-dihydroxy-2-hydroxymethyl substitution pattern. For a better insight in the validity of using NMR spectrometry for distinguishing 6/7 or 2/3 substitution in anthraquinones bearing several substituents, further NMR studies of such multiply-substituted anthraquinones seem desirable. 

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