39548-89-5

Basic information

• Product Name: 1-(4-BENZYLOXY-2-HYDROXY-6-METHOXY-PHENYL)-ETHANONE
• Synonyms: 1-(4-BENZYLOXY-2-HYDROXY-6-METHOXY-PHENYL)-ETHANONE;1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethan-1-one
• CAS NO: 39548-89-5
• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.3
• Mol File: 39548-89-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 90–91°C
• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-(4-BENZYLOXY-2-HYDROXY-6-METHOXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BENZYLOXY-2-HYDROXY-6-METHOXY-PHENYL)-ETHANONE(39548-89-5)
• EPA Substance Registry System: 1-(4-BENZYLOXY-2-HYDROXY-6-METHOXY-PHENYL)-ETHANONE(39548-89-5)

Safety Data

• Hazardous Substances Data: 39548-89-5(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of benzyl chloride on 2,4-dihydroxy-6-methoxyacetophenone with potassium carbonate in boiling acetone.

Upstream product

• 100-39-0 benzyl bromide 
• 681294-57-5 1-(4-(benzyloxy)-2-hydroxy-6-methoxyphenyl)ethanone 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 100-44-7 benzyl chloride 

Downstream Products

• 84457-62-5 2'-hydroxy-4'-benzyloxy-4,6'-dimethoxychalkone 
• 84457-62-5 (E)-1-(4-Benzyloxy-2-hydroxy-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-propenone 
• 1139263-23-2 (1R,2R,3S,3aR,8bS)-methyl 3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate 
• 1402931-89-8 C₃₈H₃₈O₁₁ 
• 1402931-83-2 (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide 
• 1402931-84-3 (1R,2R,3S,3aR,8bS)-6-cyano-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide 
• 1402931-85-4 (1R,2R,3S,3aR,8bS)-6-chloro-1,8b-dihydroxy-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide 
• 1139263-21-0 (1R,2R,3S,3aR,8bS)-3a-(4-cyanophenyl)-1,8b-dihydroxy-6,8-dimethoxy-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo-[b]cyclopenta[d]furan-2-carboxamide 
• 1402931-30-9 7-(benzyloxy)-5-methoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl 4-methoxybenzoate 
• 874202-33-2 7-(benzyloxy)-3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 960365-65-5 (1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate 
• 1402931-90-1 C₂₇H₂₃NO₇ 
• 1402931-91-2 C₂₆H₂₃ClO₇ 
• 1139263-24-3 C₂₇H₂₃NO₇ 

Relevant articles and documents

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The flavone hispidulin, a benzodiazepine receptor ligand with positive allosteric properties, traverses the blood-brain barrier and exhibits anticonvulsive effects

1 The functional characterization of hispidulin (4′,5,7-trihydroxy-6- methoxyflavone), a potent benzodiazepine (BZD) receptor ligand, was initiated to determine its potential as a modulator of central nervous system activity. 2 After chemical synthesis, hispidulin was investigated at recombinant GABA A/BZD receptors expressed by Xenopus laevis oocytes. Concentrations of 50 nM and higher stimulated the GABA-induced chloride currents at tested receptor subtypes (α 1-3,5,6β2γ2S) indicating positive allosteric properties. Maximal stimulation at α1β 2γ2S was observed with 10 μM hispidulin. In contrast to diazepam, hispidulin modulated the α6β 2γ2S-GABAA receptor subtype. 3 When fed to seizure-prone Mongolian gerbils (Meriones unguiculatus) in a model of epilepsy, hispidulin (10 mg kg-1 body weight (BW) per day) and diazepam (2 mg kg-1 BW per day) markedly reduced the number of animals suffering from seizures after 7 days of treatment (30 and 25% of animals in the respective treatment groups, vs 80% in the vehicle group). 4 Permeability across the blood-brain barrier for the chemically synthesized, 14C-labelled hispidulin was confirmed by a rat in situ perfusion model. With an uptake rate (Kin) of 1.14 ml min-1 g -1, measurements approached the values obtained with highly penetrating compounds such as diazepam. 5 Experiments with Caco-2 cells predict that orally administered hispidulin enters circulation in its intact form. At a concentration of 30 μM, the flavone crossed the monolayer without degradation as verified by the absence of glucuronidated metabolites.