1989-42-0

Basic information

• Product Name: 1,3-Dimethoxy-9,10-anthraquinone
• Synonyms: 1,3-Dimethoxy-9,10-anthraquinone;1,3-Dimethoxyanthraquinone;Xanthopurpurin dimethyl ether
• CAS NO: 1989-42-0
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Mol File: 1989-42-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 462.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.295±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,3-Dimethoxy-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethoxy-9,10-anthraquinone(1989-42-0)
• EPA Substance Registry System: 1,3-Dimethoxy-9,10-anthraquinone(1989-42-0)

Safety Data

• Hazardous Substances Data: 1989-42-0(Hazardous Substances Data)

Usage

Chemical class

Anthraquinones

Physical state

Yellow solid

Molecular weight

268.27 g/mol

Uses

a. Organic synthesis
b. Building block for dyes and pigments
c. Medicinal chemistry (anti-cancer and anti-inflammatory drugs)

Additional properties

a. Antioxidant
b. Antibacterial

Upstream product

• 602-72-2 1,3-dibromo-anthraquinone 
• 124-41-4 sodium methylate 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 106875-55-2 (Z)-(1,3-dimethoxybuta-1,3-dienyloxy)trimethylsilane 
• 57341-12-5 2-phenylsulfanyl-[1,4]naphthoquinone 
• 102580-20-1 2-benzenesulfonyl-[1,4]naphthoquinone 
• 105259-61-8 2-(phenylsulfinyl)-1,4-naphthoquinone 
• 83823-69-2 2-Benzyl-4,6-dimethoxy-benzoic acid 
• 77332-33-3 8-amino-1,3-dimethoxyanthraquinone 
• 518-83-2 xanthopurpurin 
• 74-88-4 methyl iodide 
• 85-44-9 phthalic anhydride 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 20733-99-7 1-hydroxy-3-methoxy-9,10-anthraquinone 
• 64517-23-3 1,3,10-Trimethoxy-9-phenylanthracen 

Relevant articles and documents

The preparation of anthraquinones and anthracyclinones via the reaction of haloarenes and cyanophthalides under aryne-forming conditions

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Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.

Utilization of Sulfide, Sulfoxide, and Sulfone Groups as Regiochemical Control Elements in the Diels-Alder Reaction of Naphthoquinones

The Diels-Alder reactions of 2-phenylthio-, 2-phenylsulfinyl-, and 2-phenylsulfonyl-1,4-naphthoquinones, which were unsymmetrically substituted by methoxyl group on the benzenoid ring, with some vinylketene acetals were studied.The regioselectively of the