54443-59-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-(4-methoxyphenyl)-
• Synonyms: 3-(4-methoxyphenyl)-4-oxo-4H-chromene-5,7-diyl diacetate;acetic acid 7-acetoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl ester;Biochanin A;biochanin A diacetate;4'-Methoxy-5,7-diacetoxy-isoflavon;5,7-Diacetoxy-3-(4-methoxy-phenyl)-chromen-4-on;5,7-diacetoxy-3-(4-methoxy-phenyl)-chromen-4-one
• CAS NO: 54443-59-3
• Molecular Formula: C20H16O7
• Molecular Weight: 368.343
• Mol File: 54443-59-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-(4-methoxyphenyl)-(54443-59-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,7-bis(acetyloxy)-3-(4-methoxyphenyl)-(54443-59-3)

Safety Data

• Hazardous Substances Data: 54443-59-3(Hazardous Substances Data)

Upstream product

• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 108-24-7 acetic anhydride 

Downstream Products

• 887469-00-3 acetic acid 7-acetoxy-3-(4-methoxy-phenyl)-4-thioxo-4H-chromen-5-yl ester 
• 491-80-5 5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on 

Relevant articles and documents

Synthesis and characterization of 3-arylquinazolinone and 3-arylquinazolinethione derivatives as selective estrogen receptor beta modulators

On the basis of the structure of genistein, a new series of 3-arylquinazolines was prepared and tested for their estrogen receptor (ER) α and β affinities. 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4(3H)- quinazolinone (1aa) acts as an agonist on both ER subtypes. It has 62-fold higher binding affinity [IC50(ERβ) = 179 nM] and 38-fold higher functional potency in a transcription assay [EC50(ERβ) = 76 nM] with ERβ than with ERα, thus improving upon the selectivity of genistein. All of the analogues showed preferential binding affinity for ERβ. Many are also more potent in activating transcription by ERβ than by ERα. Transformation of the C=O functionality at position 4 into a C=S group provided 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinethione (1ba), which acts as an agonist on both ER subtypes but has 56-fold higher binding affinity for ERβ over ERα [IC50(ERβ) = 47 nM] and 215-fold higher potency in the transcription assay [EC50(ERβ) = 13 nM]. These ERβ-selective compounds may represent valuable tools in understanding the differences in structure and biological function of ERβ and ERα.