6889-80-1

Basic information

• Product Name: 2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one
• Synonyms: 2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one;2-(3,4-dimethoxyphenyl)-3-hydroxychromen-4-one
• CAS NO: 6889-80-1
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29006
• Mol File: 6889-80-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 452.3°C at 760 mmHg
• Flash Point: 166.7°C
• Appearance: /
• Density: 1.342g/cm³
• Vapor Pressure: 5.7E-09mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one(6889-80-1)
• EPA Substance Registry System: 2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one(6889-80-1)

Safety Data

• Hazardous Substances Data: 6889-80-1(Hazardous Substances Data)

Usage

Description

2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one, also known as 2-(3,4-Dimethoxyphenyl)-3-hydroxy-4H-1-benzopyran-4-one, is a flavonoid compound characterized by the presence of a 3,4-dimethoxyphenyl group and a hydroxyl group on its structure. It exhibits potential biological activities, making it a promising candidate for various applications in the pharmaceutical and healthcare industries.

Uses

Used in Pharmaceutical Industry:
2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one is used as a possible inhibitor of α-Glucosidase for managing diabetes. Its ability to inhibit α-Glucosidase can help in reducing the breakdown of carbohydrates into glucose, thus controlling blood sugar levels.
Used in Anticancer Applications:
2-(3,4-diMethoxyphenyl)-3-hydroxy-4H-chroMen-4-one is used as an anticancer agent, exhibiting potential antitumor properties. Its flavonoid structure may contribute to its ability to target and inhibit the growth of cancer cells, making it a valuable compound for cancer research and therapeutic development.

InChI:InChI=1/C17H14O5/c1-20-13-8-7-10(9-14(13)21-2)17-16(19)15(18)11-5-3-4-6-12(11)22-17/h3-9,19H,1-2H3

Upstream product

• 79140-20-8 2'-hydroxy-3,4-dimethoxychalcone 
• 118-93-4 o-hydroxyacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6344-21-4 3',4'-dimethoxyflavanone 
• 19152-36-4 (E)-2'-hydroxy-3,4-dimethoxychalcone 
• 81289-17-0 3-nitro-2-(3,4-dimethoxyphenyl)-2H-chromene 

Downstream Products

• 812654-63-0 2-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-3-yl 4-methoxybenzoate 
• 78933-15-0 2-(3,4-dimethoxyphenyl)-3-methoxy-4H-chromen-4-one 

Relevant articles and documents

Bismuth(III) Flavonolates: The Impact of Structural Diversity on Antibacterial Activity, Mammalian Cell Viability and Cellular Uptake

A series of homoleptic and heteroleptic bismuth(III) flavonolate complexes derived from six flavonols of varying substitution have been synthesised and structurally characterised. The complexes were evaluated for antibacterial activity towards several problematic Gram-positive (Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), and vancomycin-resistant Enterococcus (VRE)) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria. The cell viability of COS-7 (monkey kidney) cells treated with the bismuth flavonolates was also studied to determine the effect of the complexes on mammalian cells. The heteroleptic complexes [BiPh(L)2] (in which L=flavonolate) showed good antibacterial activity towards all of the bacteria but reduced COS-7 cell viability in a concentration-dependent manner. The homoleptic complexes [Bi(L)3] exhibited activity towards the Gram-positive bacteria and showed low toxicity towards the mammalian cell line. Bismuth uptake studies in VRE and COS-7 cells treated with the bismuth flavonolate complexes indicated that Bi accumulation is influenced by both the substitution of the flavonolate ligands and the degree of substitution at the bismuth centre.

Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors

Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.

Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction

The first decarbonylative insertion of an alkyne through C?H/C?C activation of six-membered compounds is reported. The Ru-catalyzed reaction of 3-hydroxy-2-phenyl-chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro-indenebenzofuranones. Unlike previously reported metal-catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide.