2961-04-8

Usage

Family

Anthraquinone

Type

Naturally occurring organic compound

Color

Red pigment

Natural Sources

Various plants, lichens, and fungi

Industrial Use

Dyeing and coloring in the textile industry

Chemical Structure

Three hydroxyl groups attached to an anthraquinone core

Pharmacological Properties

a. Antioxidant
b. Anti-inflammatory
c. Anticancer effects

Traditional Medicine Uses

a. Laxative
b. Diuretic

InChI:InChI=1/C14H8O5/c15-7-3-1-2-6-10(7)14(19)12-9(17)5-4-8(16)11(12)13(6)18/h1-5,15-17H

Upstream product

• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 1594-64-5 1,4,8-Trichloroanthraquinone 
• 496-64-0 3-hydroxy-2-pyrone 
• 475-38-7 5,8-Dihydroxy-1,4-naphthoquinone 
• 64831-67-0 1,4-dihydroxy-5-methoxy-9,10-anthracenedione 
• 64831-62-5 2-<2,5-Dimethoxy-benzoyl>-6-methoxy-benzoesaeure 
• 75314-06-6 1,4,5-triacetoxy-9,10-anthraquinone 
• 86278-83-3 4-ethylenedioxy-(3-nitromethyl)-pentanal 
• 69043-83-0 1,4-dioxo-1,2,3,4-tetrahydro-5,9,10-trihydroxyanthracene(leuco 1,4,5-trihydroxy-9,10-anthraquinone) 
• 98122-88-4 8,9-dihydroxy-10-chloro-1,4-anthraquinone 
• 98122-61-3 8-methoxy-9-hydroxy-10-chloro-1,4-anthraquinone 
• 78048-08-5 5-hydroxy-1,4-dimethoxyanthraquinone 
• 98122-86-2 7-Hydroxy-2,2-dioxo-1,3-dioxa-2λ⁶-thia-benzo[de]anthracene-8,11-dione 
• 78048-09-6 4,5-dihydroxy-1-methoxyanthraquinone 

Downstream Products

• 81-60-7 1,4,5,8-tetrahydroxy-anthraquinone 
• 476-56-2 islandicin 
• 117-12-4 1,5-dihydroxyanthraquinone 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 132000-29-4 5-Deoxy-3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10',-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose hemihydrate 
• 132000-30-7 (4S)-2-O-Benzyl-2-C-methyl-3-O-formyl-4-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2-anthryl)-α,β-D-erythro-tetrafuranose 
• 132000-30-7 (4R)-2-O-Benzyl-2-C-methyl-3-O-formyl-4-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α(β)-D-erythro-tetrafuranose hemihydrate 
• 132000-34-1 (5R)-3-O-Benzyl-3-C-methyl-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-β-D-ribopyranose 
• 132000-34-1 (5S)-3-O-Benzyl-3-C-methyl-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2-anthryl)-α,β-D-ribopyranose 
• 132024-68-1 (5R)-3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose hemihydrate 
• 132000-36-3 (5S)-3-O-Benzyl-3-C-methyl-1,2-O-isopropylidene-5-(9',10'-dihydro-1',4',5'-trihydroxy-9',10'-dioxo-2'-anthryl)-α-D-ribofuranose 

Relevant academic research and scientific papers

Synthesis and activity of substituted anthraquinones against a human filarial parasite, Brugia malayi

Lymphatic filariasis (elephantiasis) is a global public health problem caused by the parasitic nematodes Wuchereria bancrofti and Brugia malayi. We have previously reported anthraquinones from daylily roots with potent activity against pathogenic trematode Schistosoma mansoni. Here we report the synthesis of novel anthraquinones A-S and their antifilrarial activity. Anthraquinones A-S were synthesized by a single-step Friedel-Crafts acylation reaction between phthalic anhydrides and substituted benzenes. The antifilarial properties of these synthetic anthraquinones were tested against microfilaria as well as adult male and female worms of B. malayi. The most active anthraquinone was K, which showed 100% mortality within 1, 5, and 3 days, respectively, against microfilaria and adult male and female worms at 5 ppm concentration. Albendazole, an oral drug currently used to treat parasitic infections, was used as a positive control. Methylated products of anthraquinones did not affect the microfilaria. Histological examination of treated adult female parasites showed most of the anthraquinones caused marked effects on intrauterine embryos.

Novel anthraquinones and process for the preparation and method of use thereof

A process for the preparation of hydroxyl substituted anthraquinones is described. The process couples a phthalic anhydride (substituted or unsubstituted) to benzene ring moiety substituted with at least two hydroxyl groups. Remaining hydroxy groups were converted to methoxy groups in some anthraquinones. The compounds are particularly useful for the treatment of parasitic diseases. Also, a method of treating or preventing malaria, filariasis schistosomiasis and other parasitic diseases using anthraquinones.

Carminomycinone precurses and analogues

A compound of formula II and tautomeric forms thereof wherein: R1 -R4 are H, alkyl, aryl, alkaryl, halogen, hydroxy, alkoxy, aryloxy, aralkoxy, acyloxy, amino or alkylamino: R8 has the same meaning as given to R1 -R4 or may be glycosyloxy; R9 and R12 have the same meaning as given to R1 -R4 and alternatively may be alkoxycarbonyl, aryloxycarbonyl or carboxy; one of Rx or Rb is hydroxy and the other is H, hal, alkoxy, aryloxy or acyloxy; R10 and R11 taken together are oxo or ethylenedioxy (provided that if R1 and R11 taken together are ethylenedioxy then if R4 is hydrogen or methoxy, Rb is not hydrogen or acetoxy); or R10 is hydroxy; and R11 is hydroxyalkyl or dihydroxyalkyl or --CO--R15 where R15 is H, alkyl, aryl, aralkyl, hydroxyalkyl.

SOME EXPERIMENTS WITH AMINODIHYDROXYANTHRAQUINONES

4-Amino-1-hydroxy-8-methoxyanthraquinone has been synthesized and alkylated with 1-nitropropane to give a mixture of 2- and 3-propyl compounds. Leuco-5-hydroxyquinizarin regioselectively reacts with n-propylamine and benzylamine to give 4-imino compounds, which are shown by (14)N n.m.r. spectroscopy to exist in solution as zwitterions. The benzylamine is regioselectively alkylated with propanal to give 4-benzylamino-1,5-dihydroxy-2-propylanthraquinone.

Regioselective reactions of 1,4,5-trihydroxy-9,10-anthraquinone

The regioselective alkylation of 1,4,5-trihydroxy-9,10-anthraquinone via reaction of its leuco compound is significant for the synthesis of anthracyclinones.In the presence of pyrrolidine in toluene solution, the leuco compound 3 selectively forms the 4-pyrrolidino enamine 11, which undergoes deamination to give 1,5-dihydroxy-9,10-anthraquinone.If an aldehyde is added, however, the enamine is alkylated, eventually yielding the 3-alkyl-1,4,5-trihydroxy-9,10-anthraquinone.Both of the above rections of 3 give high yields with 100percent regioselectivity.The enamine intermediate 11 has been trapped by oxidation to 4-pyrrolidino-1,5-dihydroxy-9,10-anthraquinone, which, after reduction, undergoes the same reactions as 3 giving either the alkylation or deamination product.The selective formation of 11 is explained terms of an enhancement of carbonyl group electrophilicity by a relay of hydrogen bonds.

REGIOSELECTIVE REACTIONS OF 9-HYDROXY-10-CHLORO-1,4-ANTHRAQUINONE. SYNTHESIS OF DIGITOPURPONE AND ISLANDICIN

9-Hydroxy-10-chloro-1,4-anthraquinone, obtained in the reaction of 1,4-dihydroxy-9,10-anthraquinone with thionyl chloride, is nitrated selectively at the peri position to the chlorine atom and is converted into 5-nitro-9-hydroxy-10-chloro-1,4-anthraquinone.The isomeric 8-nitro-9-hydroxy-10-chloro-1,4-anthraquinone is formed during the hydrolysis of the nitration product and the subsequent reaction of 5-nitro-1,4-dihydroxy-9,10-anthraquinone with thionyl chloride.The reaction of 9-hydroxy-10-chloro-1,4-anthraquinone and its nitro derivatives with the carbanion generated from malonic ester leads to selective alkylation at position 3.Together, the indicated reactions make it possible to realize the regioselective synthesis of 2-methyl-1,4,8- and 2-methyl-1,4,5-trihydroxy-9,10-anthraquinones.