Anthrone 1,8-dihydroxy-10-

It has been found that numerous plants contain I-C-substituted an-hydroalditols. For example, barbaloin, a major constituent of commercial aloin, is 10-(a-D-glucopyranosyl)-l,8-dihydroxy-3-(hydroxy-methyl)anthrone.45 Numerous other 1-C-substituted anhydroalditols have been isolated from a variety of plant sources by various investigators. 

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. 

The anthranoid compounds, which can be chemically described as dihydroxy-anthraquinones, -dianthrones and -anthrones, possess a laxative... 

Barbaloin was first isolated in 1851, but an acceptable structure was not proposed until 1952, when Miihlemann showed that condensation of aloe-emodin anthrone Ql,8-dihydroxy-3-(hydroxymethyl)anthrone, 7, R = CH2OH] with tetra-O-acetyl-a-D-glucopyranosyl bromide in acetone in... 

Depending on experimental conditions, sodium boioliydride reduction of anthraquinone, in a lower aliphatic alcohol, results in 9,10-dihydroxyanthracene (3) [4981-662] 9,lO-dihydro-9,10-dihydroxy-anthracene (4) [70143-55-4] anthrone (5) [90 14-8], and anthrol (6) [529-86-2] (12) ... 

A chiral bicyclic guanidine 12 was found to be an excellent catalyst for Diels-Alder reactions between anthrones and various dienophiles [35]. The catalyst can torelate a range of substituents and substitution patterns, making several anthrone derivatives suitable for this reaction. The use of 1.8-dihydroxy-9-anthrone as an anthrone substrate led to the production of 5-substituted anthrone as a Michael adduct in excellent yields, high regioselectivities and high enantioselectivities (Scheme 4.12). 

The reactions of thienothiophene derivatives in the absence of a solvent were also described. For example, the solid-state thermally induced rearrangement of 9,10-dihydroxy-9,10-bis(thieno[3,2- >]thiophen-2-yl)-9,10-dihydroanthracene (275) occurs at 240 °C and gives 10,10-bis(thieno[3,2- >]thiophen-2-yl)anthrone (276) (2000JA1082). 

The therapeutic application of some drugs is due to 1,8-dihydroxy-anthraquinones they contain. The single compounds may occur in the quinone, anthranol or anthrone form, or possibly as glucosides or dimers [195,227]. As a rule, mixtures of many compoimds of this class occur in the plants. Since their activities are not identical, the analytical determination of the individual compounds is attempted. 

The formation of colored products by the reaction of sugars and phenols in the presence of strong acids has been mentioned previously as a qualitative test for carbohydrates. Carbazole or anthrone may be used instead of a phenol. Methods employing orcinol (3,5-dihydroxy toluene) and carbazole have been described in detail 31). Dische 32) described a modified carbazole reaction for determining ketohexoses, ketopentoses, trioses, and glycolic aldehyde as well as a method for determining heptoses. 

Digiovanni J, Boutwell R K 1983 Tumor promoting activity of l,8-dihydroxy-3-methyl-9-anthrone (chrysarobin) in female Senear mice. Carcinogenesis 4 281-284... 

Diphenylnaphthacenequinone did not combine with phenylmagnesium bromide but gave the expected dihydroxy compound with phenyllithium. It is to be noted that anthrone and anthraquinone, havii only benzene nuclei, fail to react with phenylmagnesium bromide in the conjugate manner. Moreover naphthacenequinone which, like benzanthrone, has the benzene and naphthalene nuclei in competition with one another is vulnerable only in the naphthalene nucleus. 

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