58322-78-4

Usage

Uses

Used in Pharmaceutical Industry:
1,2,8-Trihydroxy-3-methylanthraquinone is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure and functional groups may contribute to its bioactivity, making it a candidate for the development of new drugs or drug delivery systems.
Used in Cosmetic Industry:
1,2,8-Trihydroxy-3-methylanthraquinone may be utilized in the cosmetic industry due to its potential antioxidant and anti-inflammatory properties. These characteristics can be beneficial in the formulation of skincare products, contributing to skin health and protection against environmental stressors.
Used in Research and Development:
1,2,8-TRIHYDROXY-3-METHYLANTHRAQUINONE can be employed in research and development settings to study its chemical properties, potential interactions with biological systems, and its applicability in various fields such as medicine, agriculture, and material science.

InChI:InChI=1/C15H10O5/c1-6-5-8-11(15(20)12(6)17)14(19)10-7(13(8)18)3-2-4-9(10)16/h2-5,16-17,20H,1H3

Upstream product

• 477-85-0 1,7-Dihydroxy-8-methoxy-6-methyl-9,10-anthraquinone 
• 108637-77-0 (1S,4aR,9aS)-8-Hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone 
• 108637-81-6 (1R,4aS,9aR)-9a-Chloro-8-hydroxy-1-methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone 
• 37418-88-5 3-hydroxyphthalic anhydride 
• 488-17-5 3-methylbenzene-1,2-diol 
• 481-74-3 Chrysophanol 
• 108637-73-6 (E)-1-Methoxy-3-methyl-1,2-bis-trimethylsilanyloxy-buta-1,3-diene 
• 108637-71-4 Methyl 3-methyl-2-trimethylsiloxy-2-butenoate 

Downstream Products

• 74272-75-6 2-methoxychrysophanol 

Relevant academic research and scientific papers

Cytochrome P450 mediated metabolic activation of chrysophanol

Chrysophanol, a major anthraquinone component occurring in many traditional Chinese herbs, is accepted as important active component with various pharmacological actions such as antibacterial and anticancer activity. Previous studies demonstrated that exposure to chrysophanol induced cytotoxicity, but the mechanisms of the toxic effects remain unknown. In the present metabolism study, three oxidative metabolites (M1-M3, aloe-emodine, 7-hydroxychrysophanol, and 2-hydroxychrysophanol) and five GSH conjugates (M4-M8) were detected in rat and human liver microsomal incubations of chrysophanol supplemented with GSH, and the formation of the metabolites was NADPH dependent except M4 and M5. M4 and M5 were directly derived from parent compound chrysophanol, M6 arose from M2, and M7 and M8 resulted from the oxidation of M4 and M5. Metabolites M5 and M6 were also observed in bile of rats after exposure to chrysophanol, M1-M3 and one NAC conjugate (M9) were detected in urine of rats administrated chrysophanol, and urinary metabolite M9 originated from the degradation of biliary GSH conjugation M6. Recombinant P450 enzyme incubation and microsome inhibition studies demonstrated that P450 1A2 was the primary enzyme responsible for the metabolic activation of chrysophanol and that P450 2B6 and P450 3A4 also participated in the generation of the oxidative metabolites. These findings helped us to understand the mechanisms of chrysophanol-induced cytotoxicity.

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.

SYNTHESIS OF SPECIFICALLY O-ALKYLATED ANTHRAQUINONES BY CYCLOADDITION

Cycloadducts from naphthoquinonoid dienophiles and 1-methoxy-1-trimethylsilyloxy butadienes undergo controlled aromatisation to form chiefly α-hydroxy- or α-methoxy-anthraquinones; this has led to synthesis of several natural O-methyl polyoxyanthraquinones.