53084-06-3

Basic information

• Product Name: 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethan-1-one
• Synonyms: 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethan-1-one
• CAS NO: 53084-06-3
• Molecular Formula: C₁₆H₁₆O₆
• Molecular Weight: 304.29464
• Mol File: 53084-06-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 184–186°C
• Appearance: /
• CAS DataBase Reference: 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethan-1-one(53084-06-3)
• EPA Substance Registry System: 2-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethan-1-one(53084-06-3)

Safety Data

• Hazardous Substances Data: 53084-06-3(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of 3,4-dimethoxyphenyl-acetonitrile with phloroglucinol (Hoesch reaction), ? in the presence of zinc chloride; ? in the presence of boron trifluoride etherate (59%).

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 19858-40-3 2-(3,4-Dimethoxy-phenyl)-4,6-dihydroxy-benzofuran-3-one 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 

Downstream Products

• 108971-91-1 3-(3,4-dimethoxy-phenyl)-4,5,7-trihydroxy-coumarin 
• 342643-55-4 2-(3,4-dimethoxy-phenyl)-1-(2-hydroxy-4,6-bis-methoxymethoxy-phenyl)-ethanone 
• 637750-97-1 3-(3,4-dimethoxyphenyl)-5,7-dihydroxy-2-methylchromen-4-one 
• 53084-11-0 3-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 
• 342643-60-1 3-(3,4-dimethoxy-phenyl)-5,7-bis-methoxymethoxy-chroman-4-one 
• 14736-60-8 3-(3',4'-dimethoxyphenyl)-4-hydroxy-5,7-dimethoxy-2H-1-benzopyrane-2-one 
• 111161-57-0 4-acetoxy-3-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-coumarin 

Relevant articles and documents

A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin

An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method

Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis

The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright

Synthesis of analogs of natural isoflavonoids containing phloroglucinol

Analogs of the natural isoflavonoids biochanin A and orobol were synthesized. Alkylation involving phenolic hydroxyls and the chromone ring was studied.