20733-99-7

Basic information

• Product Name: 1-Hydroxy-3-methoxy-9,10-anthraquinone
• Synonyms: 1-Hydroxy-3-methoxy-9,10-anthraquinone
• CAS NO: 20733-99-7
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 20733-99-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 193 °C
• Boiling Point: 490.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.400±0.06 g/cm3(Predicted)
• PKA: 6.73±0.20(Predicted)
• CAS DataBase Reference: 1-Hydroxy-3-methoxy-9,10-anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy-3-methoxy-9,10-anthraquinone(20733-99-7)
• EPA Substance Registry System: 1-Hydroxy-3-methoxy-9,10-anthraquinone(20733-99-7)

Safety Data

• Hazardous Substances Data: 20733-99-7(Hazardous Substances Data)

Usage

Physical form

Yellow-brown crystalline solid

Solubility

Soluble in organic solvents like ethanol and acetone

Classification

Synthetic organic compound, anthraquinone derivative

Function

Laxative agent

Mechanism of action

Stimulates smooth muscles of the colon, increases water and electrolyte content in the bowel, promotes bowel movements

Medical uses

Treatment of constipation, certain medical procedures (e.g., colonoscopy)

Safety concerns

Potential carcinogenic and genotoxic effects

Long-term use risks

Increased risk of developing cancer, particularly in the colon

Regulatory status

Banned in many countries, restricted and closely monitored in other regions

Upstream product

• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 90857-62-8 ((E)-1,3-Dimethoxy-buta-1,3-dienyloxy)-trimethyl-silane 
• 518-83-2 xanthopurpurin 
• 77-78-1 dimethyl sulfate 
• 602-72-2 1,3-dibromo-anthraquinone 
• 85-44-9 phthalic anhydride 
• 150-19-6 O-methylresorcine 
• 83823-65-8 2-Benzyl-4,6-dimethoxy-benzoic acid ethyl ester 
• 83823-69-2 2-Benzyl-4,6-dimethoxy-benzoic acid 
• 74-88-4 methyl iodide 
• 106875-55-2 (Z)-(1,3-dimethoxybuta-1,3-dienyloxy)trimethylsilane 
• 105259-61-8 2-(phenylsulfinyl)-1,4-naphthoquinone 
• 102580-20-1 2-benzenesulfonyl-[1,4]naphthoquinone 
• 57341-12-5 2-phenylsulfanyl-[1,4]naphthoquinone 

Relevant articles and documents

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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.

REACTIONS OF KETENE ACETALS-14; THE USE OF SIMPLE MIXED VINYLKETENE ACETALS IN THE ANNULATION OF QUINONES

α,β- and β,γ-unsaturated esters can be converted by strong base and chlorotrimethylsilane to the corresponding mixed vinylketene acetals which are shown to be particularly useful and generally applicable reagents for the regiospecific annulation of halogenoquinones.The reaction proceeds readily with a variety of substrates including benzoquinones.