6155-37-9

Basic information

• Product Name: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester
• Synonyms: 4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-carbonsaeure-methylester;1,3-dihydroxy-anthraquinone-3-carboxylic acid methyl ester;4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester;Rheinmethylester;rhein methyl ester
• CAS NO: 6155-37-9
• Molecular Formula: C16H10O6
• Molecular Weight: 298.252
• Mol File: 6155-37-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester(6155-37-9)
• EPA Substance Registry System: 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-, methyl ester(6155-37-9)

Safety Data

• Hazardous Substances Data: 6155-37-9(Hazardous Substances Data)

Usage

Description

2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester is a complex organic compound derived from anthracene, a type of aromatic hydrocarbon. It features a methyl ester group attached to the anthracene core, which is characterized by its unique chemical structure and properties. 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-,
methyl ester has potential applications in various fields due to its unique molecular structure and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester is used as an intermediate in the synthesis of Rhein 8-Glucoside (R318520), a compound with demonstrated cytotoxic and DNA-damaging properties towards tumor and normal human cells. Its ability to inhibit PTP1B (Human Protein Tyrosine Kinase 1B) in vitro makes it a promising candidate for the development of new therapeutic agents in the fight against cancer.
Used in Antioxidant Applications:
As an analog of Rhein (318500), which is found in the free state and as glucoside in Rheum spp, Polygonaceae (rhubarb), and in Senna leaves, 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester has the potential to be utilized as an antioxidant resource. Antioxidants are essential in various industries, including pharmaceuticals, cosmetics, and the food industry, to protect against oxidative stress and maintain the stability and shelf life of products.
Used in Research and Development:
Due to its unique chemical structure, 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-methyl ester can be employed in research and development for the synthesis of novel compounds with potential applications in various fields, such as pharmaceuticals, materials science, and chemical engineering. Its reactivity and structural features make it a valuable starting material for the development of new molecules with specific properties and functions.

Upstream product

• 61350-19-4 4,5,7-triacetoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 
• 6030-60-0 1,6,8-triacetoxy-3-methyl-9,10-anthraquinone 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 478-43-3 1,8-dihydroxy-3-carboxy-anthraquinone 
• 74-88-4 methyl iodide 
• 80301-52-6 9,10-Dihydroxy-5-methoxy-4-oxo-1,2,3,4-tetrahydro-anthracene-2-carboxylic acid methyl ester 
• 65131-09-1 7-methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone 
• 80301-53-7 4-Hydroxy-5-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 481-72-1 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione 
• 478-43-3 1,8-dihydroxy-3-carboxy-anthraquinone 

Relevant articles and documents

Upregulation of p53 through induction of MDM2 degradation: Amino acid prodrugs of anthraquinone analogs

Previously, we reported a class of MDM2-MDM4 dimerization inhibitors that upregulate p53 and showed potent anticancer activity in animal models. However, water solubility hinders their further development. Herein we describe our effort to develop a prodru

Preparation method of parietic acid-amino acid conjugate

The invention belongs to the technical field of organic compound synthesis, and particularly relates to a preparation method of a parietic acid-amino acid conjugate. The preparation method comprises the following steps of weighing 1 to 2g of methyl methacrylate; putting the methyl methacrylate into a reaction container; then adding 35 to 45ml of DMAP, 0.3 to 0.8g of strong base sodium hydride and1 to 3g of halohydrocarbon at the reaction temperature of 100 to 120 DEG C for the reaction time of 10 to 25min; then, adding 40 to 60 ml of hydrochloric acid solution; performing constant temperaturereaction for 5 to 10min; after the reaction is completed, performing extraction by dichloromethane; adding the extracted products into 35 to 38ml of sodium hydroxide solution; performing reaction atthe temperature of 50 to 60 DEG C for 15 to 30min; performing high-speed stirring; then regulating the pH into a weak acid state; adding 1 to 3g of amino-acid ester; performing room temperature stirring reaction for 5 to 10min; adding 40 to 60ml of hydrochloric acid solutions; performing constant temperature reaction for 5 to 10min; after the reaction is completed, performing extraction for 2 to 4times by dichloromethane; after the solid is separated, performing filtering; performing drying by anhydrous sodium sulfate; obtaining a finished product. The preparation method has the advantages that the dissolution is easy; the bioavailability is high; the process equipment requirement conditions are low; the process steps are simple; the synthesis rate is high, and the like.

Novel Oxidative Transformation: Regiospecific Preparation of Naturally Occurring 1-Hydroxyanthraquinones

A brief reaction sequence for synthesis of the naturally occurring anthraquinones 1-hydroxyanthraquinone (4a), 1-hydroxy-2-methylanthraquinone (4b), pachybasin (4c), chrysophanol (5a), and rhein (5c) has been developed.