4044-00-2

Basic information

• Product Name: 5,7-DIHYDROXYISOFLAVONE
• Synonyms: 5,7-DIHYDROXYISOFLAVONE;5,7-DIHYDROXY-3-PHENYL-4H-CHROMEN-4-ONE;5,7-Dihydroxy-3-phenyl-4H-1-benzopyran-4-one
• CAS NO: 4044-00-2
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Product Categories: Iso-Flavones
• Mol File: 4044-00-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 192.5 °C
• Appearance: /
• Density: 1.443 g/cm³
• Vapor Pressure: 2.67E-10mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 5,7-DIHYDROXYISOFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIHYDROXYISOFLAVONE(4044-00-2)
• EPA Substance Registry System: 5,7-DIHYDROXYISOFLAVONE(4044-00-2)

Safety Data

• Hazardous Substances Data: 4044-00-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H10O4/c16-10-6-12(17)14-13(7-10)19-8-11(15(14)18)9-4-2-1-3-5-9/h1-8,16-17H

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 140-29-4 phenylacetonitrile 
• 98-80-6 phenylboronic acid 
• 31721-94-5 5,7-dihydroxy-chromen-4-one 
• 727-71-9 2-phenyl-2',4',6'-trihydroxyacetophenone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 15485-75-3 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid ethyl ester 
• 39604-66-5 2-hydroxy-4,6-dimethoxyphenyl benzyl ketone 
• 17971-60-7 5,7-dihydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid 
• 26964-35-2 5,7-dimethoxyisoflavone 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 10147-11-2 propargyl benzene 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 98882-20-3 5,7-diacetoxy-3-phenyl-chromen-4-one 
• 19725-43-0 5-hydroxy-7-methoxy-3-phenyl-chromen-4-one 
• 36048-27-8 5,7,8-trihydroxy-3-phenyl-4H-1-benzopyran-4-one 
• 1005418-12-1 5-hydroxy-7-(methoxymethoxy)-3-phenyl-4H-chromen-4-one 
• 1456626-78-0 3-cyano-6-(2,4,6-trihydroxyphenyl)-5-phenylpyridin-2(1H)-one 
• 1445711-32-9 5-hydroxy-4-oxo-3-phenyl-4H-chromen-7-yl dimethylcarbamate 
• 1445711-90-9 7-hydroxy-8-[(4-methylpiperazin-1-yl)methyl]-5-methoxy-3-phenyl-4H-chromen-4-one 
• 1445711-78-3 7-hydroxy-5-methoxy-8-(piperidin-1-ylmethyl)-3-phenyl-4H-chromen-4-one 
• 1445711-70-5 7-hydroxy-8-[(dimethylamino)methyl]-5-methoxy-3-phenyl-4H-chromen-4-one 
• 154407-04-2 7-hydroxy-5-methoxy-3-phenyl-4H-chromen-4-one 
• 1445711-42-1 5-methoxy-4-oxo-3-phenyl-4H-chromen-7-yl dimethylcarbamate 
• 1159-75-7 7,8-dimethoxy-5-hydroxyisoflavone 
• 104311-03-7 Acetic acid 5-acetoxy-6,8-dibenzhydryl-4-oxo-3-phenyl-4H-chromen-7-yl ester 
• 104311-04-8 Acetic acid 6,8-dibenzhydryl-5-hydroxy-4-oxo-3-phenyl-4H-chromen-7-yl ester 

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, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues

A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.

Synthesis and aminomethylation of 7-hydroxy-5-methoxyisoflavones

A synthetic method for 7-hydroxy-5-methoxyisoflavones starting from 5,7-dihydroxyisoflavones was developed. Dimethylcarbamoylchloride was proposed for protection of the 7-hydroxy group. Aminomethylation of the synthesized 7-hydroxy-5-methoxyisoflavones by formaldehyde aminals was studied.