437-64-9

Basic information

• Product Name: 4',5-DIHYDROXY-7-METHOXYFLAVONE
• Synonyms: 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-7-Methoxy-;4',5-Dihydroxy-7-methoxyisoflavone 5,4'-Dihydroxy-7-methoxyisoflavone;5,4'-DIHYDROXY-7-METHOXYFLAVONE;4',5-DIHYDROXY-7-METHOXYFLAVONE;7-METHOXYAPIGENIN;GENKWANIN;APIGENIN-7-METHYL ETHER;7-Methylapigenin
• CAS NO: 437-64-9
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Product Categories: Tri-substituted Flavones;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 437-64-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: 290-292°C
• Boiling Point: 546.5°Cat760mmHg
• Flash Point: 209.7°C
• Appearance: /
• Density: 1.420
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Acetone (Very Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 6.36±0.40(Predicted)
• Stability: Hygroscopic
• BRN: 292549
• CAS DataBase Reference: 4',5-DIHYDROXY-7-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4',5-DIHYDROXY-7-METHOXYFLAVONE(437-64-9)
• EPA Substance Registry System: 4',5-DIHYDROXY-7-METHOXYFLAVONE(437-64-9)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-24/25-22-37
• Hazardous Substances Data: 437-64-9(Hazardous Substances Data)

Usage

Chemical Properties

Orange Powder

Uses

An antitumor constituent from the leaves of Aquilaria sinensis.

Definition

ChEBI: A monomethoxyflavone that is apigenin in which the hydroxy group at position 7 is methylated.

Upstream product

• 16290-50-9 3-(4-hydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 81719-04-2 4,2',6'-trihydroxy-4'-methoxychalkone 
• 921942-45-2 2-(4-aminophenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 114569-24-3 protogenkwanone 
• 78983-47-8 2,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-chromanon 
• 20486-36-6 Phegopolin 
• 74996-29-5 protogenkwanin 
• 520-29-6 5,4'-dihydroxy-7-methoxyflavanone 
• 19158-99-7 2’,4’-dimethoxy-6’-hydroxy-4-O-benzylchalcone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 3316-46-9 apigenin triacetate 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 10236-47-2 naringin 

Downstream Products

• 16290-46-3 5-benzoyloxy-2-(4-benzoyloxy-phenyl)-7-methoxy-chromen-4-one 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 16280-23-2 4',5,-diacetoxy-7-methoxyflavone 
• 114569-24-3 protogenkwanone 

Relevant articles and documents

Protogenkwanin 4'-glucoside, a new type of natural flavonoid with a non aromatic B-ring

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New C,O-Glycosylflavones from the Genus Silene

Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s

Site-selective synthesis of acacetin and genkwanin through lipase-catalyzed deacetylation of apigenin 5,7-diacetate and subsequent methylation

Candida antarctica lipase B-catalyzed deacetylation proceeded with high site-selectivity on the C-4′ acetyl group in apigenin triacetate to give apigenin 5,7-diacetate. Methylation of the liberated hydroxy group with the combination of trimethyloxonium tetrafluoroborate (Meerwein reagent) and 1,8-bis(dimethylamino)naphthalene (proton sponge) in CH2Cl2 proceeded in a quantitative manner to give the product methylated at the C-4′ hydroxy group (acacetin 5,7-diacetate). Even with the same precursor, a different methylation product at the C-7 hydroxy group (genkwanin 4′,5-diacetate) was obtained in 86% yield by applying iodomethane and Cs2CO3 in dimethyl sulfoxide (DMSO). The methylated products were deprotected to form acacetin and genkwanin. We inferred that the latter unexpected methylation was ascribable to the intermolecular migration of an acetyl group from C-7 to C-4′. DFT calculations indicated that the C-7 phenoxide ion was 12.6 kJ/mol more stable than the initially formed C-4′ phenoxide ion.