186394-50-3

Basic information

• Product Name: (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid
• Synonyms: (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid
• CAS NO: 186394-50-3
• Molecular Weight: 374.393
• Mol File: 186394-50-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid(186394-50-3)
• EPA Substance Registry System: (+/-)-2-(9,10-dihydro-1,8-dihydroxy-9-oxo-2-anthracene)-3-phenylpropionic acid(186394-50-3)

Safety Data

• Hazardous Substances Data: 186394-50-3(Hazardous Substances Data)

Upstream product

• 179738-01-3 methyl (9,10-dihydro-1,8-dimethoxy-9,10-dioxo-2-anthracene)acetate 
• 179738-00-2 methyl (9,10-dihydro-1-hydroxy-8-methoxy-9,10-dioxo-2-anthracene)acetate 
• 117566-33-3 2-Carboxymethyl-9,10-dihydro-1-hydroxy-8-methoxy-anthracene-9,10-dione 
• 117-10-2 1,8-dihydroxy-9,10-anthracenedione 
• 6407-55-2 1,8-dimethoxy-9,10-anthracenedione 
• 5539-66-2 1-hydroxy-8-methoxyanthraquinone 
• 179738-04-6 2-(1,8-Dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-3-phenyl-propionic acid methyl ester 

Downstream Products

• 186394-51-4 2-(1,8-Dihydroxy-9-oxo-9,10-dihydro-anthracen-2-yl)-3-phenyl-propionic acid methyl ester 

Relevant articles and documents

2-Anthracenonyl acetic acids as 5-lipoxygenase inhibitors

The synthesis of 2-substituted anthracenonyl acetic acid (2-AA) derivatives is described. The key step is the Marschalk reaction of 1-hydroxy-8-methoxy-anthracenedione with glycolic acid. After protection of the resulting 2-anthracenonyl acetic acid derivative, the 2-monoalkylated derivatives are selectively obtained by direct alkylation. The methodology proves quite general and allows for the introduction of various substituents onto the 2-position of the carboxylic side chain. Reduction of the anthracenediones proceeds with concomitant protecting group removal and proves final 2-AA products in good yields. The results of initial biological studies demonstrate enhanced 5-lipoxygenase inhibition compared to anthralin.