24160-14-3

Basic information

• Product Name: 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE
• Synonyms: CLADRIN;3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE;AKOS BBS-00006078;7-Hydroxy-3',4'-dimethoxyisoflavone;3-(3,4-Dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one;3-(3,4-dimethoxyphenyl)-7-hydroxy-4-chromenone;3-(3,4-dimethoxyphenyl)-7-hydroxy-chromen-4-one;3-(3,4-dimethoxyphenyl)-7-hydroxychromen-4-one
• CAS NO: 24160-14-3
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29
• Mol File: 24160-14-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 255 °C
• Boiling Point: 501.5°C at 760 mmHg
• Flash Point: 187.6°C
• Appearance: /
• Density: 1.321g/cm³
• Vapor Pressure: 1.11E-10mmHg at 25°C
• Refractive Index: 1.621
• PKA: 6.93±0.20(Predicted)
• CAS DataBase Reference: 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE(24160-14-3)
• EPA Substance Registry System: 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE(24160-14-3)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• HazardClass: IRRITANT
• Hazardous Substances Data: 24160-14-3(Hazardous Substances Data)

Usage

Description

3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE, also known as 3-(3,4-dimethoxyphenyl)-7-hydroxy-4H-chromen-4-one, is a naturally occurring isoflavone compound. It is characterized by its unique chemical structure, which includes a flavone backbone with specific substitutions at the 3' and 4' positions and a hydroxyl group at the 7th position. 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE has been the subject of research due to its potential biological activities and therapeutic applications.

Uses

Used in Pharmaceutical Industry:
3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE is used as a modulator for adenosine monophosphate-activated protein kinase (AMPK) for its potential role in regulating cellular energy balance and metabolism. AMPK is a key enzyme in cellular energy homeostasis, and its activation has been linked to various beneficial effects, including improved glucose and lipid metabolism, as well as potential anti-cancer and anti-inflammatory properties.
Used in Anticancer Applications:
3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE may be employed as an anticancer agent due to its ability to modulate AMPK, which can lead to the inhibition of tumor growth and progression. By targeting this important cellular pathway, the compound may offer a novel therapeutic approach for the treatment of various types of cancer.
Used in Metabolic Disorders:
Given its role in modulating AMPK, 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE may also be used in the treatment of metabolic disorders such as diabetes and obesity. Activation of AMPK can improve insulin sensitivity and promote fatty acid oxidation, which may help in managing these conditions.
Used in Drug Delivery Systems:
Similar to gallotannin, 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE could potentially be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By using various carriers such as organic or metallic nanoparticles, the compound's delivery to target cells and tissues can be improved, leading to better treatment outcomes.

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

Upstream product

• 24126-98-5 1-(2,4-dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethan-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 3557-22-0 1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one 
• 108-46-3 recorcinol 
• 124-63-0 methanesulfonyl chloride 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 935659-66-8 3-(3,4-dimethoxyphenyl)-7-(tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one 
• 111090-19-8 3-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-7-yl acetate 

Downstream Products

• 485-63-2 3',4',7-trihydroxyisoflavone 
• 951969-45-2 3-(3,4-dimethoxyphenyl)-9-(3-morpholin-4-ylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929828-69-3 3-(3,4-dimethoxyphenyl)-9-(thien-2-ylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929493-85-6 3-(3,4-dimethoxyphenyl)-9-(2-thien-2-ylethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929402-69-7 3-(3,4-dimethoxyphenyl)-9-(2-furylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929444-74-6 3-(3,4-dimethoxyphenyl)-9-(3-phenylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 951954-75-9 3-(3,4-dimethoxyphenyl)-9-(2-methoxyethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 951959-02-7 9-(3-methoxypropyl)-3-(3,4-dimethoxyphenyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1268612-94-7 7-(2-diethylamino-ethoxy)-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 921112-72-3 3-(3,4-dimethoxyphenyl)-7-(2-piperidin-1-yl-ethoxy)-4H-chromen-4-one 
• 1268612-93-6 3-(3,4-dimethoxyphenyl)-7-(2-pyrrolidin-1-yl-ethoxy)-4H-chromen-4-one 
• 921136-07-4 3-(3,4-dimethoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one 
• 921155-50-2 7-(2-bromo-ethoxy)-3-(3,4-dimethoxy-phenyl)-4H-chromen-4-one 
• 1268612-95-8 7-allyloxy-3-(3,4-dimethoxy-phenyl)-4H-chromen-4-one 

Relevant articles and documents

Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation

In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.

Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin

Abstract The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity.

Oxidative dimerisation of isoflavones: Synthesis of kudzuisoflavone a and related compounds

Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.