481-73-2

Usage

Uses

Due to the limited research available on 1,3,8-trihydroxy-6-hydroxymethylanthraquinone, its uses are not well-documented. However, based on the general properties of anthraquinones, it can be inferred that 1,3,8-trihydroxy-6-hydroxymethylanthraquinone may have potential applications in various industries. Some possible applications could include:
Used in Pharmaceutical Industry:
1,3,8-Trihydroxy-6-hydroxymethylanthraquinone could be used as a pharmaceutical compound for its potential therapeutic properties. Anthraquinones are known to have various biological activities, such as antimicrobial, antiviral, and anticancer effects. The presence of additional hydroxy and hydroxymethyl groups in 1,3,8-trihydroxy-6-hydroxymethylanthraquinone may enhance or modify these properties, making it a candidate for further research and development in the pharmaceutical field.
Used in Dye Industry:
1,3,8-Trihydroxy-6-hydroxymethylanthraquinone may be used as a dye or pigment in the dye industry. Anthraquinones are known for their color properties and are used in the production of various dyes and pigments. The specific structure of 1,3,8-trihydroxy-6-hydroxymethylanthraquinone could potentially offer unique color characteristics that could be valuable in the dye industry.
Used in Chemical Research:
1,3,8-Trihydroxy-6-hydroxymethylanthraquinone could be used as a research compound in the field of organic chemistry. Its unique structure and limited research make it an interesting subject for further investigation. Chemists may study its synthesis, properties, and potential reactions to gain a better understanding of anthraquinone chemistry and its applications.

InChI:InChI=1/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2

Upstream product

• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 569-05-1 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone 
• 195454-66-1 6-(hydroxymethyl)-9,10-dioxo-9,10-dihydroanthracene-1,3,8-triyl triacetate 
• 84993-87-3 6-bromomethyl-1,3,8-triacetoxyanthracene-9,10-dione 
• 20194-61-0 fallacinol ω-acetate 
• 124010-10-2 3-Carbethoxy-4-(4-chloro-2,5-dimethoxyphenyl)-3-butenoic acid 
• 124010-11-3 Ethyl 4-(acetyloxy)-6-chloro-5,8-dimethoxy-2-naphthalenecarboxylate 
• 132319-49-4 4,5,7-trimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 121210-61-5 3-(dibromomethyl)-1,6,8-trimethoxyanthracene-9,10-dione 
• 6414-42-2 1,3,8-trimethoxy-6-methyl-9,10-anthraquinone 
• 96822-98-9 1,3,8-triacetoxyanthracene-9,10-dione-6-carbaldehyde 
• 33770-95-5 6-formyl-1,3,8-trihydroxyanthracene-9,10-dione 
• 1373404-37-5 1,8-diacetoxy-3-hydroxyanthracene-9,10-dione-6-carbaldehyde 
• 152039-23-1 3-(Acetoxymethyl)-1-hydroxy-6,8-dimethoxy-9,10-anthracenedione 

Downstream Products

• 491-60-1 emodinanthrone 
• 569-05-1 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone 
• 205391-53-3 3-Benzyloxy-6-bromomethyl-1,8-dihydroxy-anthraquinone 
• 4517-57-1 4,5-dihydroxy-7-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 
• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 35688-09-6 ω-hydroxyemodin-5-methyl ether 
• 478-35-3 6,8-dihydroxy-3-(hydroxymethyl)-1-methoxyanthra-9,10-quinone 

Relevant academic research and scientific papers

A facile synthesis of emodin derivatives, emodin carbaldehyde, citreorosein, and their 10-deoxygenated derivatives and their inhibitory activities on μ-calpain

A new procedure for the preparation of emodin carbaldehyde and citreorosein was described, in which, ω,ω'-dibromomethylemodin triacetate was prepared as a key intermediate by NBSmediated bromination of 1,3,8-triacetylemodin. Reduction of emodin and citreorosein with SnCl 2 in a 1:1 mixture of HOAc and HCl afforded the corresponding anthrones in 90% and 92% yield, respectively, while the corresponding 10-desoxyemodin carbaldehyde was prepared by MnO2 oxidation of 10-desoxycitreorosein. 10-Desoxycitreorosein and emodin carbaldehyde showed feasible μ-calpain inhibitory activities with IC50 values of 20.15 and 25.77 M, respectively.

A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

Herein, a two-step chemoenzymatic process for the synthesis of medicinally important 3-deoxygenated anthra-9,10-quinones is developed. It involves a regio- and stereoselective reduction of hydroanthraquinones to (R)-configured dihydroanthracenones using an anthrol reductase of T. islandicus, followed by oxidation and dehydration to obtain deoxyanthraquinones in 65-80% yield. Comparison of the cell viability of normal human kidney HEK293 cells between anthraquinones and their deoxy derivatives revealed less toxicity for the latter.

Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications

Herein, we report the chemoenzymatic synthesis of a heterodimeric (-)-rugulosin B, homodimeric (-)-rugulosin C, and several rugulin analogues in three to four steps starting from anthraquinones. This work supports dimerization between variously substituted putative monomeric intermediates during the biosynthesis of naturally occurring (+)-rugulosin B and C.

Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis

A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4 gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.

Identification and characterization of an anthrol reductase from: Talaromyces islandicus (Penicillium islandicum) WF-38-12

An NADPH-dependent oxidoreductase from Talaromyces islandicus WF-38-12 has been identified through genome analysis. It has been shown to catalyze a regio- and stereoselective reduction of anthrols (formed in situ by the reduction of anthraquinones in the presence of Na2S2O4) to (R)-dihydroanthracenones, with high enantiomeric excess (>99%). The implications of results on the biosynthesis of deoxygenated (bis)anthraquinones and modified (bis)anthraquinones are discussed.

Synthesis and antibacterial activity of emodin and its derivatives against methicillin-resistant Staphylococcus aureus

Synthesis of the antibacterial emodin was improved using Friedel-Crafts acylation as a key step leading to 37% overall yield. In addition, 21 analogues were synthesized by structural modification of the hydroxyl and methyl groups, as well as the aromatic ring of emodin. Antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity against noncancerous Vero cells were evaluated. A structure-activity relationship (SAR) study indicated that the hydroxyl groups and the methyl group in the emodin skeleton were crucial for anti-MRSA activity. Furthermore, the presence of an iodine atom or ethylamino group on the aromatic ring enhanced the anti-MRSA activity with higher selectivity indices, while derivatives containing bromine, chlorine atoms or quaternary ammonium salt were as active as emodin. The quaternary ammonium group on the aromatic ring also led to non-cytotoxicity against Vero cells.

Chemical Reactivity of Emodin and Its Oxidative Metabolites to Thiols

Polygonum multiflorum is an herbal medicine widely employed in China. Hepatotoxicity of the herbal medicine has been well documented, but the mechanisms of the toxicity remain unknown. Emodin (EM) is a major constituent of the herb and has been reported to be hepatotoxic. The main purpose of this study was to define the metabolic pathways of EM in order to characterize the potential reactive intermediates. EM was incubated with rat liver microsomes or human liver microsomes, followed by LC-MS/MS analysis to investigate the in vitro and in vivo metabolism of EM. As a result, three monohydroxylation metabolites (M1-M3) were detected after exposure to EM: -hydroxyemodin, 2-hydroxyemodin, and 5-hydroxyemodin. Urinary M1 and M2 were detected in rats administered EM. Three mercapturic acids (M4-M6) were found in microsomal incubations containing EM, NADPH, and N-acetylcysteine. It appears that M4 originated from parent compound EM, and M5 and M6 originated from M1 and M2, respectively. Two biliary EM-derived GSH conjugates were found in EM-treated rats. One arose from direct adduction of EM with GSH, and the other was derived from M1. Cytochrome P450's 1A2, 2C19, and 3A4 were the predominant P450 enzymes to oxidize EM. The findings helped us to understand the mechanisms of EM-induced hepatotoxicity.

Characterization of emodin metabolites in Raji cells by LC-APCI-MS/MS

A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C18 AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as ω-hydroxyemodin, 3-O-methyl-ω-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol.

Synthesis and properties of ionophore conjugated hypericin derivatives

Two types of derivatives substituted with ionophoric residues at the ω,ω′-methyl groups of hypericin were synthesized. On the one hand, an open chain triethylene glycol derivative did not form stable complexes with alkali metal ions. Embedded as its deter

An expedient and efficient synthesis of naturally occurring hydroxy substituted anthraquinones

A general method for the synthesis of naturally occurring anthraquinones in high yield via Diels-Alder reaction is reported.