129-43-1

Basic information

• Product Name: 1-Hydroxy anthraquinone
• Synonyms: 10-Anthracenedione,1-hydroxy-9;1-hydroxy-10-anthracenedione;1-Hydroxy-9,10-anthraquinone;1-Hydroxyanthra-9,10-quinone;1-Hydroxyanthrachinon;1-hydroxy-anthraquinon;alpha-Hydroxyanthraquinone;Anthraquinone, 1-hydroxy-
• CAS NO: 129-43-1
• Molecular Formula: C₁₄H₈O₃
• Molecular Weight: 224.21
• EINECS: 204-946-7
• Product Categories: Anthraquinones;Hydroxyanthraquinones;Classes of Metal Compounds;Li (Lithium) Compounds;Typical Metal Compounds
• Mol File: 129-43-1.mol
• Article Data: 62

Chemical Properties

• Melting Point: 194°C
• Boiling Point: 325.61°C (rough estimate)
• Flash Point: 218.8°C
• Appearance: /
• Density: 1.2337 (rough estimate)
• Vapor Pressure: 1.79E-07mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.15±0.20(Predicted)
• CAS DataBase Reference: 1-Hydroxy anthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hydroxy anthraquinone(129-43-1)
• EPA Substance Registry System: 1-Hydroxy anthraquinone(129-43-1)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-40-36
• Safety Statements: 26-36/37/39-45
• RTECS: CB7178000
• Hazardous Substances Data: 129-43-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 350, 1990 DOI: 10.1021/jo00288a062

InChI:InChI=1/C14H8O3/c15-11-7-3-6-10-12(11)14(17)9-5-2-1-4-8(9)13(10)16/h1-7,15H

Upstream product

• 110-86-1 pyridine 
• 82-34-8 1-nitroanthraquinone 
• 85-44-9 phthalic anhydride 
• 108-95-2 phenol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 632-83-7 1-Bromoanthraquinone 
• 54016-87-4 4-hydroxy-anthrone 
• 634602-13-4 2-(3-hydroxy-benzoyl)-benzoic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 15066-25-8 9,10-dioxo-9,10-dihydro-anthracene-1-diazonium ; acetate 
• 64-19-7 acetic acid 
• 99-06-9 3-Carboxyphenol 
• 65-85-0 benzoic acid 

Downstream Products

• 82-44-0 1-chloroanthracene-9,10-dione 
• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 27354-06-9 1-Hydroxy-anthrahydrochinon 
• 82-42-8 4-chloro-1-hydroxyanthraquinone 
• 38847-04-0 2,4-dinitro-1-hydroxyanthraquinone 
• 1715-81-7 1-hydroxy-9(10H)-anthracenone 
• 30086-95-4 1,9-anthracenediol 
• 873991-74-3 9,10-diphenyl-9,10-dihydro-anthracene-1,9,10-triol 
• 123412-37-3 1-<<(4-fluorophenyl)sulfonyl>oxy>-9,10-anthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 56670-83-8 1-hydroxyanthraquinone-2-sulfonic acid 
• 36287-93-1 sodium 1-hydroxyanthraquinone-2-sulphonate 
• 76187-49-0 sodium 1-hydroxyanthraquinone-4-sulphonate 
• 76187-50-3 disodium 1-hydroxyanthraquinone-2,4-disulphonate 

Relevant articles and documents

An Improved Procedure for the Oxidative Transformation of Hydroanthracenones and Hydronaphthacenones to Hydroxyanthraquinones and Hydroxynaphthacenediones

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Synthesis of functionalized 1,4-dihydro-9,10-anthraquinones and anthraquinones by ring closing metathesis using Grubbs' catalyst

A general and straightforward synthesis of anthraquinones was developed, in which diallylation of 1,4-naphthoquinones, followed by Ring Closing Metathesis (RCM) of the resulting diallylnaphthoquinones with Grubbs' catalyst and subsequent dehydrogenation using Pd/C afforded the desired anthraquinones with regiocontrol of substituents and in good yields.

Metabolic products of fungi. III. The coloring matters of Pachybasium candidum Saccardo.

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Preparation of 3,4-Dihydroanthracen-1(2H)-ones. A Synthetic Approach to Islandicin and Digitopurpone via Difluoro1,O9>boron Chelates

Three 9,10-dihydroxyanthracen-1(2H)-one derivatives (2a-c) have been obtained by the catalytic hydrogenation of quinizarin, 1-hydroxy-5-methoxyanthraquinone, and 1-hydroxy-8-methoxyanthraquinone, respectively; in the last two reactions, monohydroxyanthracen-1(2H)-ones (4a) and (4b) are formed as by-products.The anthracenone derivatives (2a-c) were O-methylated by methyl toluene-p-sulphonate and the selective demethylation of the dimethoxy derivative (2d) to the monomethoxy derivative (2e) was effected by AlCl3.The silyl enolate (5) was unreactive toward C-methylation but the lithium enolate of the anthracenone (2d) reacted with methyl iodide to give a mixture of C-mono (2f) and C-di (6a) alkylated derivatives; in contrast, the boron enolate of (2d) reacted with methyl iodide to give exclusively the C-monomethylated derivative (2f) and this procedure was extended to the synthesis of 5-methoxy (2g) and 8-methoxy (2h) analogues of (2f).Whereas the dimethoxyanthracenone derivative (2d) is brominated (Br2-CHCl3, 0 deg C) in separate reactions to give monobromo (2i) and dibromo (6b) derivatives, the difluoroboron chelate (9a) was converted by photochemical bromination into a product (9g) of benzylic substitution; the analogue (9h) was similarly obtained from the difluoroboron chelate (9b).The boron derivatives (9g) and (9h) were transformed by methanol into hydroxydimethoxyanthracenone derivatives (2l) and (2m), and (9g) was also converted by wet alumina into the dihydroxymethoxyanthracenone (2n).The hydroxydimethoxyanthracenone (2l) and (2m) were transformed by 2,3-dichloro-5,6-dicyanobenzoquinone and selenium dioxide into 1-hydroxy-4-methoxyanthraquinone and 1-hydroxy-4-methoxy-2-methylanthraquinone, respectively.

Copper-catalyzed one-pot relay synthesis of anthraquinone based pyrimidine derivative as a probe for antioxidant and antidiabetic activity

Synthetic compounds have modernized the globe due to its vast applicable fields. Anthraquinones, as well as pyrimidine derivatives, are used as essential pharmacophores in the field of medicine. Maintenance of a green disease-free environment by using these derivatives is being acknowledged in developed as well as developing countries of the world. Considering the use of active catalysts in the synthesis of anthraquinone based derivatives are the era of concern for researchers due to their distinctive properties. Owing to the remarkable activities of anthraquinone and pyrimidine derivative, we synthesize compounds having both functionalities with the utilization of novel synergically active copper catalysts. This study explores the application of synthesized compounds using fast, ecofriendly and cost-effective approaches.1H and 13C NMR, antioxidant, antidiabetic, molecular docking and QSAR studies were used for characterization and evaluation of newly synthesized anthraquinone based pyrimidine derivatives. The result of these techniques shows that our desired compounds were successfully synthesized and have potent applications. Among all synthesized compounds, G2 and G3 showed a remarkable antioxidant activity with IC50 of 15.09 and 21.88 μg/ml respectively. While the compound G2 and G4 showed a strong inhibitory antidiabetic activity with the IC50 value of 24.23 and 28.94 μg/ml respectively. Furthermore, molecular docking results for both of the proteins assist the experimental data and confirms the different interactions between binding domains and substituent moieties. SAR study also relates to the experimental facts by giving us positive results of synthesized compounds. According to the QSAR study, G4 and G2 emerged as the most stable and most reactive compound among other compounds respectively. While MEP shows moderate to good nucleophilic and electrophilic reactivity of all four compounds.

BIFUNCTIONAL SMALL MOLECULES TO TARGET THE SELECTIVE DEGRADATION OF CIRCULATING PROTEINS

The present invention is directed to bifunctional small molecules which contain a circulating protein binding moiety (CPBM) linked through a linker group to a cellular receptor binding moiety (CRBM) which is a membrane receptor of degrading cell such as a hepatocyte or other degrading cell. In embodiments, the (CRBM) is a moiety which binds to asialoglycoprotein receptor (an asialoglycoprotein receptor binding moiety, or ASGPRBM) of a hepatocyte. In additional embodiments, the (CRBM) is a moiety which binds to a receptor of other cells which can degrade proteins, such as a LRP1, LDLR, FcyRI, FcRN, Transferrin or Macrophage Scavenger receptor. Pharmaceutical compositions based upon these bifunctional small molecules represent an additional aspect of the present invention. These compounds and/or compositions may be used to treat disease states and conditions by removing circulating proteins through degradation in the hepatocytes or macrophages of a patient or subject in need of therapy. Methods of treating disease states and/or conditions in which circulating proteins are associated with the disease state and/or condition are also described herein.

Preparation method of 4-hydroxyindole

The invention discloses a preparation method of 4-hydroxyindole, comprising the steps of (1) dissolving 3-methoxyphenylhydrazine hydrochloride in DMF (dimethylformamide), adding concentrated sulfuricacid and a catalyst, mixing well, adding acetaldehyde, allowing reflux reaction at controlled temperature of 60-80 DEG C for 90-120 min, filtering after reaction is over to obtain 4-methoxyindole; (2)dissolving 4-methoxyindole in dichloromethane, adding the obtained solution in a reactor, introducing nitrogen, controlling the temperature to 50-70 DEG C, and introducing HBr into the solution, allowing reflux reaction for 45-90 min, lowering the temperature to room temperature, performing reduced pressure removal of a solvent, and recrystallizing to obtain 4-hydroxyindole. The preparation method according to the application is simple to perform and has mild conditions and few byproducts, the product is high in purity, and the yield of the product is high.