130688-86-7

Basic information

• Product Name: (3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydro-4H-chromen-4-one
• Synonyms: 4H-1-benzopyran-4-one, 3-[(3,4-dimethoxyphenyl)methylene]-2,3-dihydro-, (3E)-
• CAS NO: 130688-86-7
• Molecular Formula: C₁₈H₁₆O₄
• Molecular Weight: 296.3172
• Mol File: 130688-86-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 481.8°C at 760 mmHg
• Flash Point: 214.7°C
• Density: 1.236g/cm³
• Vapor Pressure: 1.93E-09mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: (3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydro-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydro-4H-chromen-4-one(130688-86-7)
• EPA Substance Registry System: (3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydro-4H-chromen-4-one(130688-86-7)

Safety Data

• Hazardous Substances Data: 130688-86-7(Hazardous Substances Data)

Usage

General Description

(3E)-3-(3,4-dimethoxybenzylidene)-2,3-dihydro-4H-chromen-4-one is a chemical compound with potential pharmaceutical uses. It is a derivative of 4H-chromen-4-one, a natural product with diverse biological activities, including antitumor, anti-inflammatory, and antioxidant properties. The presence of the dimethoxybenzylidene group in the structure suggests potential applications as an anticancer agent due to its ability to inhibit tumor growth. Additionally, the compound’s chromenone scaffold makes it a promising candidate for drug development, as chromenone derivatives have shown to exhibit various pharmacological activities, making them of interest in pharmaceutical research. Further studies are necessary to fully understand the properties and potential uses of this chemical compound.

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 122273-76-1 cis (dimethoxy-3,4 benzyl)-3 chromannol-4 
• 122273-76-1 trans (dimethoxy-3,4 benzyl)-3 chromannol-4 
• 122273-82-9 3’,4’-dimethoxyhomoisoflavan 
• 1616984-36-1 3-(3,4-dimethoxystyryl)-2H-chromene 
• 1616984-21-4 C₁₉H₂₀O₄ 
• 1616984-57-6 3a,4-dihydro-4-(3,4-dimethoxyphenyl)-2-phenylchromeno[4,3-e]isoindole-1,3(2H,6H,11bH,11cH)-dione 
• 1616984-56-5 3a,4-dihydro-4-(3,4-dimethoxyphenyl)-6H-isobenzofuro[5,4-c]chromene-1,3(11bH,11cH)-dione 
• 1616984-50-9 8-(3,4-dimethoxyphenyl)-6H-benzo[c]chromene-9,9,10,10-(8H,10aH)-tetracarbonitrile 
• 98469-99-9 (3RS,3'SR)-3'-(3,4-dimethoxy-phenyl)-spiro[chroman-3,2'-oxiran]-4-one 
• 84289-41-8 3',4'-dimethoxy-3-benzyl-4-chromanone 

Relevant articles and documents

Synthesis and biological evaluation of 3-benzylidene-4-chromanone derivatives as free radical scavengers and α-glucosidase inhibitors

A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 μM; 13: EC50 14 μM; 18: EC50 13 μM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 μM; 14: IC50 25 μM; 18: IC50 28 μM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.

Synthesis of novel tricyclic heterocyclic compounds as potential anticancer agents using chromanone and thiochromanone as synthons

The arylmethylene of benzopyrane or benzothiopyrane 3,4 have been synthesized and condensed with hydrazine, guanidine and thiourea to yield pyrazole 5-8, aminopyrimidine 9,10 and thioxopyrimidine derivatives 11,12, respectively. Compounds 3 or 4 on treatment with malononitrile in the presence of ammonium acetate/acetic acid or in the presence of piperidine/ methanol to yield benzopyrano- and benzothiopyranopyridine 13,14 and benzopyrano- and benzothiopyrane 15,16, respectively. The oxirane of compound 3 is prepared and condensed with CS2 to yield the tricyclic system, thioxothienobenzopyrane 21. Ylidenemalononitrile for the ketone 1 and 2 are synthesized and condensed with aromatic aldehyde in presence of ammonium acetate/acetic acid to yield benzopyranopyridine and benzothiopyranopyridine derivatives 24,25, respectively, which are the isomer of compounds 13,14. Ylidenemalononitrile on condensation with phenylisothiocyanate yields benzo-pyrano- and benzothiopyranothioxopyridine 28,29, respectively.

THE SYNTHESIS OF BENZOPYRANOPYRIDINES AND PYRANOBENZOPYRANS

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