70460-18-3

Basic information

• Product Name: 3'-HYDROXYFLAVONE
• Synonyms: 3'-HYDROXYFLAVONE;4H-1-Benzopyran-4-one,2-(3-hydroxyphenyl)-(9CI);2-(3-hydroxyphenyl)chromen-4-one;2-(3-hydroxyphenyl)chromone;2-(3-hydroxyphenyl)-4H-chromen-4-one
• CAS NO: 70460-18-3
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 238.24
• Product Categories: FLAVONE
• Mol File: 70460-18-3.mol

Chemical Properties

• Melting Point: 206-208°C
• Boiling Point: 437.7°Cat760mmHg
• Flash Point: 170.9°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 2.86E-08mmHg at 25°C
• Refractive Index: 1.666
• PKA: 9.01±0.10(Predicted)
• CAS DataBase Reference: 3'-HYDROXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-HYDROXYFLAVONE(70460-18-3)
• EPA Substance Registry System: 3'-HYDROXYFLAVONE(70460-18-3)

Safety Data

• Hazardous Substances Data: 70460-18-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3'-Hydroxyflavone is used as a therapeutic agent for its potential antioxidant, anti-inflammatory, and anticancer properties. It is being studied for its ability to inhibit certain enzymes and pathways involved in inflammation and cancer, which may contribute to the development of new treatments for various diseases.
Used in Neuroprotection:
3'-Hydroxyflavone is used as a neuroprotective agent due to its potential to protect neurons from damage and degeneration. It has been investigated for its potential application in the treatment of neurodegenerative diseases, such as Alzheimer's and Parkinson's, where its protective effects could help slow down or prevent the progression of these conditions.
Used in Cardiovascular Disease Treatment:
3'-Hydroxyflavone is used as a treatment for cardiovascular diseases due to its potential to improve heart health and reduce the risk of heart-related complications. Its antioxidant and anti-inflammatory properties may contribute to the prevention and management of cardiovascular conditions.
Used in Metabolic Disorder Management:
3'-Hydroxyflavone is used in the management of metabolic disorders, such as diabetes and obesity, due to its potential to regulate metabolic processes and improve overall health. Its effects on inflammation and oxidative stress may help in the prevention and treatment of these disorders.

InChI:InChI=1/C15H10O3/c16-11-5-3-4-10(8-11)15-9-13(17)12-6-1-2-7-14(12)18-15/h1-9,16H

Upstream product

• 53906-83-5 3'-methoxyflavone 
• 119-36-8 methyl salicylate 
• 92496-65-6 3'-Hydroxyflavanone 
• 75848-97-4 2',3-dihydroxy-αβ-dihydrochalcone 
• 121-71-1 3-Hydroxyacetophenone 
• 98-88-4 benzoyl chloride 
• 100-83-4 meta-hydroxybenzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 214360-76-6 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 121245-86-1 1-(2-hydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 
• 517892-04-5 3',4'-dihydroxyflavone-4'-β-D-ribofuranoside sodium salt 
• 517892-03-4 3',4'-dihydroxyflavone-4'-β-D-glucopyranoside sodium salt 
• 34000-28-7 2'-hydroxy-3-methoxy-chalcone 

Downstream Products

• 405216-85-5 3'-(N,N-Dimethylcarbamoyloxy)flavone 
• 119881-50-4 2-(3-acetoxy-phenyl)-6-diacetylamino-chromen-4-one 

Relevant articles and documents

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Preference for O-demethylation reactions in the oxidation of 2′-, 3′-, and 4′-methoxyflavones by human cytochrome P450 enzymes

2′-, 3′-, and 4′-Methoxyflavones (MeFs) were incubated with nine forms of recombinant human cytochrome P450 (P450 or CYP) enzymes in the presence of an NADPH-generating system and the products formed were analyzed with LC-MS/MS methods. CYP1B1.1 and 1B1.3

Microwave-assisted synthesis of novel bis-flavone dimers as new anticancer agents

In this study, we describe a microwave-based click chemistry method used to prepare a family of novel bis-flavone dimers. The substituted 7-hydroxy and 4’-hydroxy flavonoids were linked through a triazole ring. The compounds were easily synthesized and purified in high yields. The bis-flavonoids were tested on different cell lines including HCT116, HepG2, MCF7 and MOLT-4. Several analogues showed to have anticancer activity with IC50 values in the range of 20-60 μM. Flavonoids are known for their anticancer properties and this method provides the basis for new medicinal structures.

Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE2 in LPS-induced RAW 264.7 cells

In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound 3g displayed more potent inhibitory activities on PGE2 production, similar inhibitory activities on NO production and less weak cytotoxicity than luteolin, a natural flavone known as a potent anti-inflammatory agent.

Synthesis, in vitro and Docking Studies of New Flavone Ethers as α-Glucosidase Inhibitors

We report herein the synthesis, α-glucosidase inhibition and docking studies for a series of 3-15 new flavones. A simple nucleophilic substitution reaction takes place between 3′hydroxyflavone (2) with halides to afford the new flavones. Chalcone (1), 3′h

Synthesis and antiviral activity of 2-aryl-4H-chromen-4-one derivatives against Chikungunya virus

A series of nineteen 2-aryl-4H-chromen-4-one derivatives 2a-2s were synthesized and evaluated for their antiviral activity against Chikungunya virus (LR2006-OPY1) in Vero cell culture by CPE reduction assay. Three compounds 2a, 2b and 2g, were found to be active at concentration of (IC50) 0.44 μM, 0.45 μM and 2.02 μM, respectively. Compounds having heterocyclic ring 2a and 2b at the 2nd position of the chromenone were found to be potent inhibitor of ChikV. Cytotoxicity studies were performed using Vero cell culture, compounds 2a and 2b exhibited SI of ≥100. Molecular docking simulation has been carried out to understand the possible mechanism of action.

A versatile approach to flavones via a one-pot Pd(II)-catalyzed dehydrogenation/oxidative boron-Heck coupling sequence of chromanones

A variety of flavones were expediently synthesized from readily accessible chromanones via a one-pot sequence involving Pd(ii)-catalyzed dehydrogenation and oxidative boron-Heck coupling with arylboronic acid pinacol esters. In particular, the use of arylboronic acid pinacol esters was found to significantly improve the yield of the reaction.

PPh3·HBr-DMSO: A Reagent System for Diverse Chemoselective Transformations

The broad applicability of the hitherto unexplored reagent combination PPh3·HBr-DMSO is exemplified with multiple highly diverse one-step transformations to synthetically useful building blocks, such as flavones, 4H-thiochromen-4-ones, α-hydroxy ketones, 1,4-naphthoquinones (including vitamin K3), 2-bromo-3-substituted-1H-1-indenones, 2-methylthio-1H-1-indenones, 3-butyne-1,2-dione, and 4-pentene-2,3-diones. The simple and mild reaction conditions make the reagent superior in terms of yield and substrate scope in comparison with the existing alternatives.

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 lM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.

Monoamine oxidase inhibitory activity of 2-aryl-4H-chromen-4-ones

A series of twenty 2-aryl-4H-chromen-4-one (flavones) derivatives (3a-3s) were synthesized and tested for hMAO inhibitory activity. Fifteen compounds (3a, 3c, 3e-3h, 3j-3p, 3r, 3s) were found to be selective towards MAO-B, while 3d was selective towards MAO-A, and 3b, 3i and 3q were non-selective. Experimental Selectivity Index for MAO-B ranges from 2.0 (3g, 3p) to 30.0 (3j). Compound 3j, which is carrying 3,4-di-OMeC6H3 groups at R position on the molecule, was found to be potent MAO-B inhibitor amongst the fifteen with Ki value for MAO-B of 0.16 ± 0.01 μM comparable to that of standard drug, Selegiline (Ki for MAO-B is 0.16 ± 0.01 μM). Compound 3j also appeared as the most selective MAO-B inhibitor according to its best selectivity index (30.0), which is comparable to that of Selegiline (SIMAO-B = 35.0). Molecular docking and molecular dynamics simulation studies were carried out using Autodock-4.0 and Amber12 to understand the molecular level interaction and energy relation of MAO isoforms with selective inhibitors (3d and 3j). Simulation results are in good agreement with the experimental results. Leads identified may further be explored to develop potent isoform specific inhibitors of MAO.