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

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 
• 68-12-2 N,N-dimethyl-formamide 
• 87-66-1 2-hydroxyresorcinol 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 59887-97-7 7,8-dimethoxy-4-oxo-4H-1-benzopyran 
• 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 

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.

Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives

A new class of 4-oxo-4H-1-benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA-MB-468), ovarian adenocarcinoma (SK-OV-3), and colorectal adenocarcinoma (HT-29). Two compounds, that is, 3-hexyl-7,8-dihydroxy-4-oxo-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-1-benzopyran-3-yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52-57 μM). Structure-activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

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).

CHROMEN-4-ONE DERIVATIVES AS SELF-TANNING SUBSTANCE

The invention relates to the use of compounds of the formula (I), where R1 and R2 may be identical or different and stand for H, OH, OCH3, CH3, CH2OH or CH2OCH3, R3 stands for H or straight-chain or branched C1- to C20-alkyl groups, R4 stands for H or OR8, R5 and R6 may be identical or different and are selected from —H, —OH, straight-chain or branched C1 to C20-alkyl groups, straight-chain or branched C3- to C20-alkenyl groups, straight-chain or branched C1- to C20-hydroxyalkyl groups, where the hydroxyl group may be bonded to a primary or secondary carbon atom of the chain, and furthermore the allyl chain may also be interrupted by oxygen, and R8 stands for H or straight-chain or branched C1- to C20-alkyl groups, with the proviso that R2 does not denote H if R1 denotes CH3, as self-tanning agents, and to compounds and the preparation thereof.

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.

Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata

Intricatinol and intricatin, the two homoisoflavonoids isolated from Hoffmanosseggia intricata, and two analogs have been synthesized from pyrogallol in three steps. The spectral data of synthetic intricatinol are in good agreement with those of natural metabolite, but the spectral data of intricatin are not corroborative with those of the natural product. The structure of intricatin has been thus revised to 8-methoxybonducellin, a compound isolated from Caesalpinia pulcherrima. The antioxidant activity of all the four homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The synthetic analog 7,8-dihydroxy-3-[(3,4-dihydroxyphenyl)methylene]chroman-4-one displayed excellent activity in both methods.