5539-66-2

Basic information

• Product Name: 1-Hydroxy-8-methoxyanthraquinone
• Synonyms: 1-Hydroxy-8-methoxy-9,10-anthraquinone;1-Hydroxy-8-methoxyanthraquinone;1-Methoxy-8-hydroxy-9,10-anthraquinone
• CAS NO: 5539-66-2
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 5539-66-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 196.8-198 °C
• Boiling Point: 480.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.400±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.75±0.20(Predicted)
• CAS DataBase Reference: 1-Hydroxy-8-methoxyanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-8-methoxyanthraquinone(5539-66-2)
• EPA Substance Registry System: 1-Hydroxy-8-methoxyanthraquinone(5539-66-2)

Safety Data

• Hazardous Substances Data: 5539-66-2(Hazardous Substances Data)

Usage

Type of compound

Synthetic organic compound

Family

Anthraquinones

Physical form

Red dye

Uses

Dyeing fabrics in the textile industry, production of paints, inks, and crayons

Medicinal properties

Anti-inflammatory and anti-cancer properties, traditionally used in herbal medicine

Potential use

Photodynamic therapy for the treatment of certain cancers

Safety concerns

Toxic effects, should be handled with care.

Upstream product

• 43101-75-3 9,10-dihydro-8-hydroxy-9,10-dioxoanthracen-1-yl acetate 
• 77-78-1 dimethyl sulfate 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 860562-36-3 3-methoxy-2-salicyl-benzoic acid 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 80-48-8 methyl p-toluene sulfonate 
• 85313-87-7 1-allyloxy-8-methoxyanthracene-9,10-dione 
• 84399-87-1 (4α,4aβ,9aβ)-8-hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone 
• 122630-07-3 (4aR,9aR)-8-Methoxy-9a-phenylsulfanyl-4a,9a-dihydro-4H-anthracene-1,9,10-trione 
• 84399-87-1 8-Hydroxy-1,1,4-trimethoxy-1,4,4a,9a-tetrahydro-anthraquinone 
• 75312-39-9 1-Acetoxy-8-methoxy-9,10-anthrachinon 
• 6407-55-2 1,8-dimethoxy-9,10-anthracenedione 
• 54648-79-2 N,N’-diisopropyl-O-methylisourea 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 

Downstream Products

• 186394-66-1 4-[(9,10-dihydro-9,10-dioxo-1-hydroxy-8-methoxy-2-anthracenyl)hydroxymethyl]benzonitrile 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 6407-55-2 1,8-dimethoxy-9,10-anthracenedione 
• 95636-48-9 1-hydroxy-8-methoxy-2-(1-oxo-2-sulfoxophenylpentyl)anthraquinone 
• 92811-05-7 1-hydroxy-8-methoxy-2-(1'-oxo-2'-phenylthiopentyl)anthraquinone 
• 139565-46-1 Acetic acid 8-acetoxy-2-benzyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 139565-45-0 Acetic acid 2-benzyl-8-methoxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester 
• 139565-40-5 2-Benzyl-1,8-dihydroxy-anthraquinone 
• 34425-60-0 isochrysophanol 
• 179738-05-7 2-(1,8-Dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-4-phenyl-butyric acid methyl ester 
• 179738-04-6 2-(1,8-Dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-3-phenyl-propionic acid methyl ester 
• 186394-54-7 (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-4-phenylbutanoic acid 
• 186394-50-3 (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid 
• 186394-59-2 4-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracene-2-carbonyl)-benzoic acid methyl ester 

Relevant articles and documents

Intramolecular addition of carbanions to anthraquinones

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Methylation of 1,8-dihydroxy-9,10-anthraquinone with and without use of solvent-free technique

A convenient and environmentally friendly solvent-free procedure has been developed for dimethylation of 1,8-dihydroxy-9,10-anthraquinone with excellent yield. A highly selective monomethylation of 1,8-dihydroxy-9,10-anthraquinone in refluxing tetraglyme makes monomethylated peri-dihydroxy-9,10-anthraquinones easily available. Alternatively, irradiation in a domestic microwave oven has been employed for the solvent-free monomethylation of 1,8-dihydroxy-9,10-anthraquinone.

Efficient reductive Claisen rearrangement of prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones with iron powder in ionic liquids

A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2’-enyloxyanthraquinones and 2’-chloroprop-2’-enyloxyanthraquinones to 1-hydroxy-2-(prop-2’-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF4 (1-methylimidazolium tetrafluoroborate), in short reaction times (5–35 min). Our study showed that 1-(prop-2’-enyloxy)anthraquinone is more active than 1-(2’-chloroprop-2’-enyloxy)anthraquinone to perform this rearrangement.

Synthesis and enhanced DNA cleavage activities of bis-tacnorthoamide derivatives

A new metal-free DNA cleaving reagent, bis-tacnorthoamide derivative 1 with two tacnorthoamide (tacnoa) units linked by a spacer containing anthraquinone, has been synthesized from triazatricyclo[5.2.1.04,10]decane and characterized by NMR and mass spectrometry. For comparison, the corresponding compounds mono-tacnorthoamide derivative 2 with one tacnorthoamide unit and 6 with two tacnorthoamide units linked by an alkyl (1,6-hexamethylene) spacer without anthraquinone have also been synthesized. The DNA-binding property investigated via fluorescence and CD spectroscopy suggests that compounds 1 and 2 have an intercalating DNA binding mode, and the apparent binding constants of 1, 2 and 6 are 1.3 × 107 M-1, 0.8 × 10 7 M-1 and 8 × 105 M-1, respectively. Agarose gel electrophoresis was used to assess plasmid pUC19 DNA cleavage activity promoted by 1, 2, 6 and parent tacnoa under physiological conditions, which gives rate constants kobs of 0.2126 ± 0.0055 h-1, 0.0620 ± 0.0024 h-1, 0.040 ± 0.0007 h-1 and 0.0043 ± 0.0002 h-1, respectively. The 50-fold and 15-fold rate acceleration over parent tacnoa is because of the anthraquinone moiety of compound 1 or 2 intercalating into DNA base pairs via a stacking interaction. Moreover, DNA cleavage reactions promoted by compound 1 give 5.3-fold rate acceleration over compound 6, which further demonstrates that the introduction of anthraquinone results in a large enhancement of DNA cleavage activity. In particular, DNA cleavage activity promoted by 1 bearing two tacnoa units is 3.3 times more effective than 2 bearing one tacnoa unit and the DNA cleavage by compound 1 was achieved effectively at a relatively low concentration (0.03 mM). This dramatic rate acceleration suggests the cooperative catalysis of the two positively charged tacnoa units in compound 1. The radical scavenger inhibition study and ESI-MS analysis of bis(2,4-dinitrophenyl) phosphate (BDNPP) and adenylyl(3′-5′) phosphoadenine (APA) cleavage in the presence of compound 1 suggest the cleavage mechanism would be via a hydrolysis pathway by cleaving the phosphodiester bond of DNA.