569-92-6

Basic information

• Product Name: 3,5,4''-TRIHYDROXY-7-METHOXYFLAVONE
• Synonyms: 4H-1-Benzopyran-4-one, 3,5-dihydroxy-2-(4-hydroxyphenyl)-7-methoxy-;7-Methylkaempferol;Kaempferol 7-methyl ether
• CAS NO: 569-92-6
• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26288
• Product Categories: Flavanols
• Mol File: 569-92-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 225-227℃
• Boiling Point: 571.9°Cat760mmHg
• Flash Point: 218.4°C
• Appearance: /
• Density: 1.538
• Vapor Pressure: 6.45E-14mmHg at 25°C
• Refractive Index: 1.709
• Storage Temp.: 2-8°C
• PKA: 6.18±0.40(Predicted)
• CAS DataBase Reference: 3,5,4''-TRIHYDROXY-7-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,4''-TRIHYDROXY-7-METHOXYFLAVONE(569-92-6)
• EPA Substance Registry System: 3,5,4''-TRIHYDROXY-7-METHOXYFLAVONE(569-92-6)

Safety Data

• Hazardous Substances Data: 569-92-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A monomethoxyflavone that is the 7-methyl ether derivative of kaempferol.

InChI:InChI=1/C16H12O6/c1-21-10-6-11(18)13-12(7-10)22-16(15(20)14(13)19)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3

Synthetic route

7-O-methyl-3,4',5-tri-O-acetylkaempferol (13323-01-8) → rhamnocitrin (569-92-6)

Conditions	Yield
Stage #1: 7-O-methyl-3,4',5-tri-O-acetylkaempferol With ammonia In methanol at 20℃; for 3h; Stage #2: With hydrogenchloride In methanol at 20℃; for 12h;	97%

5,7-dimethoxy-3-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (77316-40-6) → rhamnocitrin (569-92-6)

Conditions	Yield
With aniline hydrochloride at 180℃;

3,5,7-trimethoxy-4'-hydroxyflavonol (59259-80-2) → rhamnocitrin (569-92-6)

Conditions	Yield
With aluminium trichloride; nitrobenzene

dimethyl sulfate (77-78-1) + Aromadendrin (480-20-6, 22425-48-5, 104486-98-8, 118333-31-6) → rhamnocitrin (569-92-6)

Conditions	Yield
With potassium carbonate; acetone

rhamnocitrin-O-α-L-rhamnopyranoside (57525-01-6) → rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; ethanol for 1h; Heating;	124 mg

7-O-Methyldihydrokaempferol, 7-O-methylaromadendrin (37971-69-0) → rhamnocitrin (569-92-6)

Conditions	Yield
With air In sulfuric acid for 4h; Heating;
With air In sulfuric acid for 4h; Heating;

3t,5-dihydroxy-2r-<4-hydroxy-phenyl>-7-methoxy-chroman-4-one → rhamnocitrin (569-92-6)

Conditions	Yield
With sodium hydroxide Leiten von Luft durch die erhaltene Loesung;
Erwaermen mit wss. Schwefelsaeure;
Erhitzen mit basischem Wismutcarbonat, Essigsaeure und 2-Aethoxy-aethanol;

2'-hydroxy-2,4',6'-trimethoxyacetophenone (17874-42-9) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium-<4-benzoyloxy benzoate> / 180 °C / Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge 2: nitrobenzene; aluminium chloride View Scheme

4-(benzoyloxy)benzoyl chloride (58860-84-7) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether; pyridine / anschliessend Behandeln mit wss. Salzsaeure 2: potassium-<4-benzoyloxy benzoate> / 180 °C / Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge 3: nitrobenzene; aluminium chloride View Scheme

4-benzoyloxy-benzoic acid-anhydride (205652-96-6) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium-<4-benzoyloxy benzoate> / 180 °C / Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge 2: nitrobenzene; aluminium chloride View Scheme

(+/-)-3t-hydroxy-2r-(4-hydroxy-phenyl)-5,7-dimethoxy-chroman-4-one (26207-83-0, 37971-70-3) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: basic bismuth carbonate; acetic acid; 2-ethoxy-ethanol 2: aniline hydrochloride / 180 °C View Scheme

rhamnocitrin 3-O-α-L-arabinopyranoside → rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride In ethanol; water at 80℃;	2.1 mg

rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside (1391144-80-1) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->3)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside (1391144-81-2) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->4)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside (1391144-82-3) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-β-D-galactopyranoside (1391144-83-4) → D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-β-D-galactopyranoside-4'-O-β-D-glucopyranoside (1391144-84-5) → D-glucose (50-99-7) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-α-L-rhamnopyranosyl-(1->2)-β-D-galactopyranoside (1391144-85-6) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

rhamnocitrin-3-O-α-L-rhamnopyranosyl-(1->6)-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside (1391144-89-0) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 6h;

7-O-methylkaempferol 3-O-(α-L-rhamnopyranosyl-(1→6)-O-β-D-galactopyranoside) → L-Rhamnose (3615-41-6) + D-Galactose (59-23-4) + rhamnocitrin (569-92-6)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 3h;

3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-chromen-4-one (16274-11-6) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one; thiophenol; 1H-imidazole / 11 h / 0 °C 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: ammonia / methanol / 3 h / 20 °C 3.2: 12 h / 20 °C View Scheme

kaempferol (520-18-3) → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: pyridine / 20 °C 2.1: 1-methyl-pyrrolidin-2-one; thiophenol; 1H-imidazole / 11 h / 0 °C 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: ammonia / methanol / 3 h / 20 °C 4.2: 12 h / 20 °C View Scheme

3,4',5-tri-O-acetylkaempferol → rhamnocitrin (569-92-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: ammonia / methanol / 3 h / 20 °C 2.2: 12 h / 20 °C View Scheme

rhamnocitrin (569-92-6) → kaempferol (520-18-3)

Conditions	Yield
With hydrogen iodide; acetic anhydride; phenol at 130℃; for 0.5h;

hydrogen iodide (10034-85-2) + rhamnocitrin (569-92-6) → kaempferol

acetic anhydride (108-24-7) + rhamnocitrin (569-92-6) → 7-O-methyl-3,4',5-tri-O-acetylkaempferol (13323-01-8)

Conditions	Yield
With pyridine

Upstream product

• 77316-40-6 5,7-dimethoxy-3-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 
• 59259-80-2 3,5,7-trimethoxy-4'-hydroxyflavonol 
• 77-78-1 dimethyl sulfate 
• 480-20-6 Aromadendrin 
• 57525-01-6 rhamnocitrin-O-α-L-rhamnopyranoside 
• 37971-69-0 7-O-Methyldihydrokaempferol, 7-O-methylaromadendrin 
• 17874-42-9 2'-hydroxy-2,4',6'-trimethoxyacetophenone 
• 58860-84-7 4-(benzoyloxy)benzoyl chloride 
• 205652-96-6 4-benzoyloxy-benzoic acid-anhydride 
• 26207-83-0 (+/-)-3t-hydroxy-2r-(4-hydroxy-phenyl)-5,7-dimethoxy-chroman-4-one 
• 1391144-80-1 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 
• 1391144-81-2 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->3)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 
• 1391144-82-3 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->4)]-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 
• 1391144-83-4 rhamnocitrin-3-O-[(S)-3-hydroxy-3-methylglutaryl-(1->6)]-β-D-galactopyranoside 

Downstream Products

• 520-18-3 kaempferol 
• 13323-01-8 7-O-methyl-3,4',5-tri-O-acetylkaempferol 

Relevant articles and documents

Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

A strategy for selective mono-, di- and tri-O-methylation of kaempferol, predominantly on the basis of selective benzylation and controllable deacetylation of kaempferol acetates, was developed. From the selective deacetylation and benzylation of kaempferol tetraacetate (1), 3,4′,5,-tri-O-acetylkaempferol (2) and 7-O-benzyl-3,4′5,-tri-O-acetylkaempferol (8) were obtained, respectively. By controllable deacetylation and followed selective or direct methylation of these two intermediates, eight O-methylated kaempferols were prepared with 51-77% total yields from kaempferol.

3-hydroxy-3-methylglutaryl flavonol glycosides from Oxytropis falcata

Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

Chemical Studies on the Constituents of Hyphear Tanakae HOSOKAWA from Different Host Trees

The chemical constituents of Hyphear Tanakae HOSOKAWA epiphyting to four different host trees were examined.A new triterpene fatty acid ester (III) and four known flavonoid glycosides, rhamnocitrin-3-O-rhamnoside (V), kaempferol-3-O-rhamnoside (VI), rhamnetin-3-O-rhamnoside (VII), and quercetin-3-O-rhamnoside (VIII) have been isolated from the leaves and twigs of this plant epiphyting to Castanea crenata SIEB., together with fatty acids (I), phytosterol (II), and phytosterol-glucoside (IV).The present investigation has revealed that compounds II-V, VII, and VIII are contained in this plant irrespective of the host, among the four host trees, examined.Keywords - Hyphear Tanakae; misletoe; Loranthaceae; triterpene; lup-20(29)-ene-3β,7β,15α-triol; flavonoid; rhamnocitrin-3-O-rhamnoside; kaempferol-3-O-rhamnoside; rhamnetin-3-O-rhamnoside; quercetin-3-O-rhamnoside