59887-89-7

Basic information

• Product Name: 7-hydroxy-4-benzopyrone
• Synonyms: 7-hydroxy-4-benzopyrone;7-Hydroxy-4-chromone;7-Hydroxy-4H-1-benzopyran-4-one, 7-Hydroxybenzopyran-4-one;7-Hydroxy-4H-1-benzopyran-4-one;7-Hydroxychromone;Einecs 261-973-7;7-Hydroxy-4-chroMone 97%;7-Hydroxybenzopyran-4-one
• CAS NO: 59887-89-7
• Molecular Formula: C₉H₆O₃
• Molecular Weight: 162.14214
• EINECS: 261-973-7
• Mol File: 59887-89-7.mol
• Article Data: 33

Chemical Properties

• Melting Point: 215-220 °C
• Boiling Point: 345.4°C at 760 mmHg
• Flash Point: 148.1°C
• Appearance: /
• Density: 1.403g/cm³
• Vapor Pressure: 3.08E-05mmHg at 25°C
• Refractive Index: 1.64
• PKA: 7.07±0.20(Predicted)
• CAS DataBase Reference: 7-hydroxy-4-benzopyrone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-hydroxy-4-benzopyrone(59887-89-7)
• EPA Substance Registry System: 7-hydroxy-4-benzopyrone(59887-89-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 59887-89-7(Hazardous Substances Data)

Usage

Description

7-Hydroxy-4-benzopyrone, also known as 7-Hydroxy-4-chromone, is a 4-oxo-4H-1-benzopyran derivative with potential applications in various fields due to its ability to inhibit Src kinase with an IC50 of less than 300 μM. 7-hydroxy-4-benzopyrone is characterized by its unique chemical structure and biological activity, making it a promising candidate for further research and development.

Uses

Used in Pharmaceutical Applications:
7-Hydroxy-4-benzopyrone is used as a pharmaceutical agent for its ability to inhibit Src kinase, which plays a crucial role in various cellular processes, including cell proliferation, survival, and migration. The inhibition of Src kinase by this compound may have therapeutic implications in the treatment of various diseases, particularly those involving abnormal cell growth or signaling pathways.
Used in Cancer Research:
In the field of cancer research, 7-hydroxy-4-benzopyrone is used as a potential anticancer agent. Its ability to inhibit Src kinase may help in the development of targeted therapies for cancer treatment, as Src kinase is often overactivated in various types of cancer, contributing to tumor growth and progression.
Used in Drug Development:
7-Hydroxy-4-benzopyrone can be utilized in the development of new drugs, particularly those aimed at targeting Src kinase or related signaling pathways. Its unique chemical structure and biological activity make it a valuable starting point for the design and synthesis of novel therapeutic agents.
Used in Chemical Synthesis:
As a 4-oxo-4H-1-benzopyran derivative, 7-hydroxy-4-benzopyrone may also find applications in chemical synthesis, serving as a building block or intermediate for the creation of more complex molecules with diverse biological activities.

InChI:InChI=1/C9H6O3/c10-6-1-2-7-8(11)3-4-12-9(7)5-6/h1-5,10H

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 122-51-0 orthoformic acid triethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 108-46-3 recorcinol 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 5751-52-0 7-methoxy-4H-chromen-4-one 
• 108982-01-0 7-benzyloxy-4-oxo-4H-chromene-2-carboxylic acid 
• 30113-83-8 7-hydroxy-4-oxo-4H-chromene-2-carboxylic acid 
• 860189-36-2 4-(4-benzyloxy-2-hydroxy-phenyl)-2,4-dioxo-butyric acid ethyl ester 
• 6345-73-9 7-benzyloxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 151254-88-5 8-amino-7-<(6-phenylhexyl)oxy>-4-chromanone 
• 151254-87-4 8-amino-7-<4-<(4-methoxyphenyl)oxy>butoxy>-4-chromanone 
• 166529-53-9 8-nitro-7-<(6-phenylhexyl)oxy>chromone 
• 1025880-74-3 7-[4-(4-Methoxy-phenoxy)-butoxy]-8-nitro-chromen-4-one 
• 131323-76-7 7-{3-[Ethyl-(3-phenyl-propyl)-amino]-propoxy}-chromen-4-one 
• 105277-32-5 7-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-33-6 7-[3-(4-phenylpiperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-34-7 7-[3-(4-(4-chlorophenyl)piperazinyl)propoxy]-4H-1-benzopyran-4-one 
• 105277-56-3 7-[3-(4-Phenyl-1-piperidinyl)propoxy]-4H-1-benzopyran-4-one 
• 131323-73-4 7-[3-(4-Phenyl-[1,4]diazepan-1-yl)-propoxy]-chromen-4-one 
• 131323-55-2 7-[3-(4-Benzyl-piperazin-1-yl)-propoxy]-chromen-4-one 
• 105277-68-7 7-[4-(4-Phenyl-piperazin-1-yl)-butoxy]-chromen-4-one 
• 105277-52-9 7-[3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propoxy]-chromen-4-one 
• 131323-58-5 7-[3-(2,3,5,6-Tetrahydro-[1,2']bipyrazinyl-4-yl)-propoxy]-chromen-4-one 

Relevant articles and documents

Anti-HIV agents. Part 55: 3′R,4′R-Di-O-(-)-camphanoyl-2′,2′- dimethyldihydropyrano[2,3-f]chromone (DCP), a novel anti-HIV agent

3′R,4′R-Di-O-(-)-camphanoyl-2′,2′- dimethyldihydropyrano[2,3-f]chromone (DCP) (2) was designed and synthesized on the basis of a structure-activity relationship study of 3′R,4′R-di-O-(-)-camphanoyl-(+)-cis-khellactone DCK (1) and its analogues. DCP (2), a pyranochromone, and DCK (1), a pyranocoumarin, have different skeletons. Compound 2 showed potent in vitro inhibition of HIV-1 replication in H9 lymphocyte cells with an EC50 of 6.78×10-4 μM and TI of 14,500. These values are comparable with those for DCK (1) and better than those of AZT in the same assay.

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.

Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer's disease

A new serise of 7-hydroxy-chromone derivatives bearing pyridine moiety were synthesized, and evaluated as multifunctional agents against Alzheimer's disease (AD). Most of the compounds were good AChE inhibitors (IC50 = 9.8–0.71 μM) and showed remarkable BuChE inhibition activity (IC50 = 1.9–0.006 μM) compared with donepezil as the standard drug (IC50 = 0.023 and 3.4 μM). Compounds 14 and 10 showed the best inhibitory activity toward AChE (IC50 = 0.71 μM) and BuChE (IC50 = 0.006 μM), respectively. The ligand–protein docking simulations and kinetic studies revealed that compound 14 and 10 could bind effectively to the peripheral anionic binding site (PAS) of the AChE and BuChE through mixed-type inhibition. In addition, the most potent compounds showed acceptable neuroprotective activity on H2O2- and Aβ-induced.neurotoxicity in PC12 cells, more than standard drugs. The compounds could block effectively self- and AChE-induced Aβ aggregation. All the results suggest that compounds 14 and 10 could be considered as promising multi-target-directed ligands against AD.