59887-99-9

Basic information

• Product Name: 7,8-Dihydroxy-4H-1-benzopyran-4-one
• Synonyms: 7,8-Dihydroxy-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 7,8-dihydroxy-;7,8-dihydroxy-4H-chromen-4-one
• CAS NO: 59887-99-9
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14
• Mol File: 59887-99-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 402.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.563±0.06 g/cm3(Predicted)
• PKA: 6.91±0.20(Predicted)
• CAS DataBase Reference: 7,8-Dihydroxy-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-Dihydroxy-4H-1-benzopyran-4-one(59887-99-9)
• EPA Substance Registry System: 7,8-Dihydroxy-4H-1-benzopyran-4-one(59887-99-9)

Safety Data

• Hazardous Substances Data: 59887-99-9(Hazardous Substances Data)

Upstream product

• 934391-20-5 3-(2,3-dihydroxylphenoxy)propanenitrile 
• 528-21-2 2',3',4'-trihydroxyacetophenone 
• 122-51-0 orthoformic acid triethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 87-66-1 2-hydroxyresorcinol 

Downstream Products

• 934391-18-1 C₁₆H₁₂O₅ 
• 124166-26-3 (E)-7,8-dihydroxy-3-(4-methoxybenzylidene)chroman-4-one 
• 934391-19-2 3-((E)-3,4-dihydroxy-benzylidene)-7,8-dihydroxy-chroman-4-one 
• 59887-97-7 7,8-dimethoxy-4-oxo-4H-1-benzopyran 

Relevant articles and documents

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.

A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2,4,6-trichloro-1,3,5-triazine/ dimethylformamide

A mild and efficient one-flask method has been developed for the synthesis of chromones, isoflavones, and homoisoflavones from 2-hydroxyacetophenones, deoxybenzoins, and dihydrochalcones, respectively, via one-carbon extension using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide. Deoxybenzoins and dihydrochalcones were prepared in situ by the reaction of readily available substituted phenols with phenylacetic acids and 3-phenylpropanoic acids, respectively. This method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. The methodology has been applied to the synthesis of three naturally occurring isoflavones such as formononetin (9c), daidzein (9d), and retusin (9h).

Isoflavone glycosides: Synthesis and evaluation as α-glucosidase inhibitors

On the basis of the structure of 4′,7,8-trihydroxyisoflavone 7-O-α-D-arabinofuranoside (namely A-76202, 1), a Rhodococcus metabolite showing potent inhibitory activities against the α-glucosidases of rat liver microsome (IC50 = 0.46 ng/mL), 26 analogs, each with minor variations at the sugar moiety and the isoflavone A and B rings, were readily synthesized. Notably, a new and efficient method was developed for the divergent synthesis of the B-ring congeners of the isoflavone glycosides by using Suzuki-Miyaura coupling as the final step. Modifications at the sugar moiety and the isoflavone A ring significantly diminish the activity, whereas variations at the B ring are largely tolerated for retaining the potent α-glucosidase inhibitory activity. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.