52869-21-3

Basic information

• Product Name: 1-Hydroxy-5-methoxyanthraquinone
• Synonyms: 1-Hydroxy-5-methoxy-9,10-anthraquinone;1-Hydroxy-5-methoxyanthraquinone;1-hydroxy-5-methoxyanthracene-9,10-dione
• CAS NO: 52869-21-3
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 52869-21-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Hydroxy-5-methoxyanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-5-methoxyanthraquinone(52869-21-3)
• EPA Substance Registry System: 1-Hydroxy-5-methoxyanthraquinone(52869-21-3)

Safety Data

• Hazardous Substances Data: 52869-21-3(Hazardous Substances Data)

Usage

Chemical Family

Anthraquinone

Physical Appearance

Red dye

Industrial Uses

+ Textile dyeing
+ Wood staining

Medicinal Applications

+ Antitumor agent
+ Inhibitor of platelet activation
+ Antioxidant properties
+ Anti-inflammatory properties

Ongoing Research

Potential therapeutic benefits.

Upstream product

• 6448-90-4 1,5-dimethoxy-anthraquinone 
• 85809-74-1 1-hydroxy-5-methoxy-anthrone 
• 102851-23-0 5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-8-(2-methoxy-phenyl)-bicyclo[4.2.0]octa-1,3,5-trien-7-one 
• 112740-65-5 (4aR^*,9aR^*)-5-methoxy-1-oxo-9a-(phenylthio)-1,4,4a,9a-tetrahydro-9,10-anthraquinone 
• 117-12-4 1,5-dihydroxyanthraquinone 
• 77189-69-6 5-acetoxy-2-bromo-1,4-naphthoquinone 
• 105259-49-2 5-methoxy-2-(phenylthio)-1,4-naphthoquinone 
• 71700-92-0 5-acetoxy-2-(phenylthio)-1,4-naphthoquinone 
• 71700-93-1 5-hydroxy-2-(phenylthio)-1,4-naphthoquinone 
• 112740-64-4 (1R^*,4aR^*,9aR^*)-5-methoxy-9a-(phenylthio)-1-<(trimethylsilyl)oxy>-1,4,4a,9a-tetrahydro-9,10-anthraquinone 
• 102808-59-3 3-(tert-butyldimethylsiloxy)benzocyclobutenedione 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 34817-14-6 5-chloro-9,10-dioxo-9,10-dihydro-anthracene-1-sulfonic acid 

Downstream Products

• 116161-94-5 2-benzyl-hydroxy-5-methoxy-9,10-anthraquinone 
• 116161-93-4 1-hydroxy-2-hydroxybenzyl-5-methoy-9,10-anthraquinonenone 
• 6448-90-4 1,5-dimethoxy-anthraquinone 
• 128462-02-2 C₃₇H₃₄O₉ 
• 136459-81-9 Phenyl-(5,9,10-trimethoxy-1-methoxymethoxy-anthracen-2-yl)-methanol 
• 136459-85-3 2-Benzyloxy-2-methyl-1-(5,9,10-trimethoxy-1-methoxymethoxy-anthracen-2-yl)-pent-4-en-1-ol 
• 136459-92-2 C₃₈H₃₆O₉ 
• 136460-00-9 Benzoic acid (R)-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-hydroxy-2-methyl-pent-4-enyl ester 
• 136460-00-9 Benzoic acid (S)-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-hydroxy-2-methyl-pent-4-enyl ester 
• 136459-97-7 (S)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol 
• 136459-97-7 (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol 
• 136459-99-9 Benzoic acid (S)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-methyl-pent-4-enyl ester 
• 136459-99-9 Benzoic acid (R)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-methyl-pent-4-enyl ester 
• 136459-98-8 Benzoic acid (S)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-enyl ester 

Relevant articles and documents

Experiments Directed Towards the Synthesis of Anthracyclinones. XXVI. The Preparation of Chiral Intermediates for Anthracyclinone Synthesis

(2'R)-1,5-Dimethoxy-2-(2'-methyloxiran-2'-ylmethyl)anthraquinone (8), an intermediate for the synthesis of fridamycin E, has been prepared enantioselectively via the diol (15).The diol (15) was prepared in high yield by asymmetric cis-hydroxylation of the alkene (11).The analogous diol (22), a vineomycinone B2 precursor, was also prepared.

Regioselective synthesis of 2- and 3-(Phenylthio)juglone derivatives

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Selective Dealkylation of Methoxyanthraquinones via Difluoro1,O9>boron Chelates: Synthesis of Hydroxymethoxyanthraquinones

1,8-, 1,5- 1,2-, and 1,4-Dimethoxyanthraquinones have been treated with boron trifluoride-diethyl ether to give difluoro(anthraquinonato)boron chelates (1a-d) respectively. 1,4,5-Trimethoxyanthraquinone was similarly converted separately in benzene and toluene into the mono- (2) and bis-difluoroboron(3)-chelates respectively, and 2,2',4,4'-tetramethoxybenzophenone was converted by BF3*Et2O in toluene into the boron adduct (4).Treatment of these derivatives, (1a-d) and (2)-(4), with methanol gave the following uncomplexed derivatives in good yield respectively: 1-hydroxy-8-methoxyanthraquinone, 1-hydroxy-5-methoxyanthraquinone, 1-hydroxy-2-methoxyanthraquinone, 1-hydroxy-4-methoxyanthraquinone, 4-hydroxy-1,5-dimethoxyanthraquinone, 1,4-dihydroxy-5-methoxyanthraquinone, and 2-hydroxy-2',4,4'-trimethoxybenzophenone.