22812-15-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-[4-(phenylmethoxy)phenyl]-
• CAS NO: 22812-15-3
• Molecular Formula: C24H20O5
• Molecular Weight: 388.42
• Mol File: 22812-15-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-[4-(phenylmethoxy)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-[4-(phenylmethoxy)phenyl]-(22812-15-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,7-dimethoxy-2-[4-(phenylmethoxy)phenyl]-(22812-15-3)

Safety Data

• Hazardous Substances Data: 22812-15-3(Hazardous Substances Data)

Upstream product

• 4397-53-9 p-benzyloxybenzaldehyde 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 100-39-0 benzyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 19158-99-7 2’,4’-dimethoxy-6’-hydroxy-4-O-benzylchalcone 
• 392302-39-5 acetic acid 2-[3-(4-benzyloxy-phenyl)-2,3-dibromo-propionyl]-3,5-dimethoxy-phenyl ester 
• 392302-10-2 4'.6'-dimethoxy-4-benzyloxy-2'-acetoxy-trans-chalcone 
• 19158-99-7 (E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 392302-47-5 Acetic acid 2-[(Z)-3-(4-benzyloxy-phenyl)-2-bromo-acryloyl]-3,5-dimethoxy-phenyl ester 

Downstream Products

• 94805-83-1 Isolicoflavonol 
• 437-64-9 genkwanin 
• 16290-50-9 3-(4-hydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 

Relevant articles and documents

Rocaglaol phenolic hydroxyl derivative as well as preparation method and application thereof

The invention discloses a rocaglaol phenolic hydroxyl derivative and a preparation method and an application thereof, the rocaglaol phenolic hydroxyl derivative has the following structural formula (I), in the structural formula (I), R is methyl, ethyl, propyl, butyl, amyl, hexyl, 5-bromoamyl, allyl, isopentenyl, propargyl, 2-butynyl, acetyl, propionyl, valeryl, benzoyl, p-nitrobenzoyl, ethyl sulfonyl, propyl sulfonyl or phenyl sulfonyl. The compound has nano-mole-level anti-colorectal cancer and anti-leukemia activity.

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

Synthesis method of isolicoflavonol

The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.