489-35-0

Basic information

• Product Name: GOSSYPETIN
• Synonyms: 3,3',4',5,7,8-Hexahydroxyflavone;8-Hydroxyquercetin;Articulatidin;C.I.75750;Equisporol;GOSSYPETIN(RG);2-(3,4-Dihydroxyphenyl)-3,5,7,8-tetrahydroxy-4H-1-benzopyran-4-one;3,5,7,8,3',4'-HEXAHYDROXYFLAVONE
• CAS NO: 489-35-0
• Molecular Formula: C₁₅H₁₀O₈
• Molecular Weight: 318.24
• Product Categories: Flavanols
• Mol File: 489-35-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 302-304°C
• Boiling Point: 679.3 °C at 760 mmHg
• Flash Point: 260.6 °C
• Appearance: /
• Density: 1.912
• Vapor Pressure: 4.49E-19mmHg at 25°C
• Refractive Index: 1.863
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated))
• PKA: 6.47±0.40(Predicted)
• CAS DataBase Reference: GOSSYPETIN(CAS DataBase Reference)
• NIST Chemistry Reference: GOSSYPETIN(489-35-0)
• EPA Substance Registry System: GOSSYPETIN(489-35-0)

Safety Data

• Hazardous Substances Data: 489-35-0(Hazardous Substances Data)

Usage

Uses

3,5,7,8,3'',4''-Hexahydroxyflavone is a flavonoid found in H. sabdariffa and has diverse biological activities/properties. 3,5,7,8,3'',4''-Hexahydroxyflavone is the anxiolytic and antidepressant constituents of H. sabdariffa calyces.

InChI:InChI=1/C15H10O8/c16-6-2-1-5(3-7(6)17)14-13(22)12(21)10-8(18)4-9(19)11(20)15(10)23-14/h1-4,16-20,22H

Synthetic route

2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,7,8-trimethoxy-chromen-4-one (27500-35-2) → gossypetin (489-35-0)

Conditions	Yield
With hydrogen iodide; acetic anhydride

gossypetin 8-O-β-D-glucuronide 3-sulphate → gossypetin (489-35-0)

Conditions	Yield
With hydrogenchloride at 100℃;

gossypetin-3.5.8.3'.4'-pentamethyl ether → gossypetin (489-35-0)

Conditions	Yield
With hydrogen iodide

5,7,3',4'-tetrahydroxy-3,8-dimethoxyflavone (4988-22-1) → gossypetin (489-35-0)

Conditions	Yield
With hydrogen iodide; phenol at 145℃; for 0.5h;	4 mg

7,8,3',4'-tetrahydroxy-3,5-dimethoxyflavone → gossypetin (489-35-0)

Conditions	Yield
With hydrogen bromide for 0.5h; Heating;	5 mg

quercetol (117-39-5) → gossypetin (489-35-0)

Conditions	Yield
With NADPH; flavin adenine dinucleotide In phosphate buffer at 30℃; for 0.25h; pH=7.0; Enzyme kinetics; Further Variations:; Reagents; pH-values; Temperatures;

gossypetin-3,8-dimethyl ether 5-O-β-D-glucopyranoside → gossypetin (489-35-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: β-glucosidase; acetate buffer / 24 h / 37 °C / pH 5.2 2: 4 mg / HI; phenol / 0.5 h / 145 °C View Scheme

sinocrassoside D2 (909803-33-4) → L-Rhamnose (3615-41-6) + D-glucose (50-99-7) + gossypetin (489-35-0)

Conditions	Yield
With hydrogenchloride; water for 3h; Reflux;

gossypetin-3-O-α-L-arabinofuranoside → gossypetin (489-35-0)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 4h;

gossypetin-3-O-α-rhamnopyranoside → gossypetin (489-35-0)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 4h;

gossypetin-3-O-β-xylopyranoside → gossypetin (489-35-0)

Conditions	Yield
With hydrogenchloride; water at 100℃; for 4h;

gossypetin (489-35-0) + acetic anhydride (108-24-7) → C25H20O13

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 12h;	70%

gossypetin (489-35-0) + methyl iodide (74-88-4) → 3,5-dihydroxy-7,8,3',4'-tetramethoxyflavone (72620-07-6)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 12h;	10%

diazomethane (186581-53-3, 908094-01-9) + gossypetin (489-35-0) → 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one (14965-12-9)

Conditions	Yield
With methanol; diethyl ether

gossypetin (489-35-0) + acetic anhydride (108-24-7) → 3,5,7,8-tetraacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one (42215-76-9)

gossypetin (489-35-0) + ethyl iodide (75-03-6) → 3,5,7,8-tetraethoxy-2-(3,4-diethoxy-phenyl)-chromen-4-one

Conditions	Yield
With potassium hydroxide; ethanol

gossypetin (489-35-0) + dimethyl sulfate (77-78-1) → 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one (14965-12-9)

Conditions	Yield
With potassium carbonate; acetone; benzene

gossypetin (489-35-0) + dimethyl sulfate (77-78-1) → hexa-O-methylogossypetin (7741-47-1)

Conditions	Yield
With potassium carbonate; acetone

gossypetin (489-35-0) + methyl iodide (74-88-4) → hexa-O-methylogossypetin (7741-47-1)

Conditions	Yield
With methanol Behandeln des Reaktionsgemischs mit methylalkoholischer Kalilauge;

gossypetin (489-35-0) → 3,5-dihydroxyphenol (108-73-6) + 3,4-Dihydroxybenzoic acid (99-50-3)

Conditions	Yield
bei der Kalischmelze;

gossypetin (489-35-0) → 2-(3,4-dihydroxy-phenyl)-7-hydroxy-chromene-3,4,5,8-tetraone

Conditions	Yield
With air Ansaeuern der Loesung;
With ethanol; p-benzoquinone

gossypetin (489-35-0) → quercetagetin (90-18-6)

Conditions	Yield
With hydrogen iodide; phenol at 180℃;

gossypetin (489-35-0) + hydrogen iodide (10034-85-2) + phenol (108-95-2) → quercetagetin (90-18-6)

Conditions	Yield
at 180℃;

gossypetin (489-35-0) + methyl iodide (74-88-4) + methanolic KOH-solution → gossypetin-hexamethyl ether

ethanol (64-17-5) + gossypetin (489-35-0) + p-benzoquinone (106-51-4) → gossypitone

gossypetin (489-35-0) + alkali + air → gossypitone

Conditions	Yield
beim Ansaeuern;

gossypetin (489-35-0) → C26H22O13

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; tetrahydrofuran / 12 h / 20 °C 2: potassium carbonate / acetone / 12 h / 60 °C View Scheme

gossypetin (489-35-0) + ampelopsin (27200-12-0) → C29H18O15

Conditions	Yield
With polyphenol oxidase at 20 - 40℃; pH=3.5 - 5.5; Enzymatic reaction;

Upstream product

• 117-39-5 quercetol 
• 4988-22-1 5,7,3',4'-tetrahydroxy-3,8-dimethoxyflavone 
• 27500-35-2 2-(3,4-dimethoxy-phenyl)-3-hydroxy-5,7,8-trimethoxy-chromen-4-one 
• 909803-33-4 sinocrassoside D₂ 

Downstream Products

• 90-18-6 quercetagetin 
• 72620-07-6 3,5-dihydroxy-7,8,3',4'-tetramethoxyflavone 
• 108-73-6 3,5-dihydroxyphenol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 7741-47-1 hexa-O-methylogossypetin 
• 14965-12-9 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one 
• 42215-76-9 3,5,7,8-tetraacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one 

Relevant articles and documents

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Three new flavonoids, proanthocyanidin, and accompanying phenolic constituents from Feijoa sellowiana

Our investigation of phenolic constituents of fruits, flower buds, and leaves of Feijoa sellowiana led to the isolation of twenty-one phenolics including three new gossypetin glycosides 1-3, and also the purification of a proanthocyanidin fraction. A high-performance liquid chromatography method for simultaneous analysis of phenolic constituents was established and then used to investigate the phenolic profiles of the parts of the plant species, to show the presence of characteristic flavonoids and ellagic acid derivatives or ellagitannins in the extracts from fruits, flower buds, and leaves. The branch extract profile also suggested the presence of alkylated ellagic acids as characteristic constituents. Inhibitory effects of feijoa flavonoids on mushroom tyrosinase were seen, although in some cases this may have resulted from direct interaction with the enzyme. Cytotoxic effect of the proanthocyanidin fraction was also shown.

Bioactive constituents from chinese natural medicines. XXXII.1 aminopeptidase N and aldose reductase inhibitors from sinocrassula indica: Structures of sinocrassosides B4, B5, C1, and D1-D3

From the methanolic extract of the whole plant of Sinocrassula indica (Crassulaceae), six new flavonol glycosides, sinocrassosides B4 (1), B5 (2), C1 (3), D1 (4), D2 (5), and D3 (6), were isolated together with 30 compounds. The structures of 1-6 were elucidated on the basis of chemical and physicochemical evidence. In addition, several constituents were found to show inhibitory effects on aminopeptidase N and aldose reductase.