247564-47-2

Basic information

• Product Name: 5,7-dihydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one
• Synonyms: 5,7-dihydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one
• CAS NO: 247564-47-2
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26348
• Mol File: 247564-47-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,7-dihydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dihydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one(247564-47-2)
• EPA Substance Registry System: 5,7-dihydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one(247564-47-2)

Safety Data

• Hazardous Substances Data: 247564-47-2(Hazardous Substances Data)

Upstream product

• 247564-48-3 5,7-dihydroxy-3-(2-methoxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid ethyl ester 
• 116854-95-6 2-(2-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 
• 7035-03-2 2-methoxy-benzeneacetonitrile 
• 108-73-6 3,5-dihydroxyphenol 

Downstream Products

• 70943-68-9 Irilin C 
• 1445711-50-1 5-methoxy-3-(2-methoxyphenyl)-4-oxo-4H-chromen-7-yl dimethylcarbamate 
• 1445711-60-3 7-hydroxy-5-methoxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 1445711-87-4 7-hydroxy-5-methoxy-3-(2-methoxyphenyl)-8-(piperidin-1-ylmethyl)-4H-chromen-4-one 
• 1445711-93-2 7-hydroxy-8-[(4-methylpiperazin-1-yl)methyl]-5-methoxy-3-(2-methoxyphenyl)-4H-chromen-4-one 
• 1445712-03-7 7-hydroxy-5-methoxy-3-(2-methoxyphenyl)-8-(morpholin-4-ylmethyl)-4H-chromen-4-one 
• 1445711-40-9 5-hydroxy-3-(2-methoxyphenyl)-4-oxo-4H-chromen-7-yl dimethylcarbamate 

Relevant articles and documents

Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones

In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

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.

Synthesis of analogs of natural isoflavonoids containing phloroglucinol

Analogs of the natural isoflavonoids biochanin A and orobol were synthesized. Alkylation involving phenolic hydroxyls and the chromone ring was studied.