Product Name

  • Name

    Fisetin

  • EINECS 208-434-4
  • CAS No. 528-48-3
  • Article Data12
  • CAS DataBase
  • Density 1.688 g/cm3
  • Solubility
  • Melting Point 330 ºC
  • Formula C15H10O6
  • Boiling Point 599.4 ºC at 760 mmHg
  • Molecular Weight 286.241
  • Flash Point 233 ºC
  • Transport Information
  • Appearance yellow to brown crystalline powder
  • Safety 22-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 528-48-3 (Fisetin)
  • Hazard Symbols
  • Synonyms Fisetin(6CI);Flavone, 3,3',4',7-tetrahydroxy- (8CI);2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-benzopyran-4-one;3,3',4',7-Tetrahydroxyflavone;5-Desoxyquercetin;Bois Bleu de Honqrie;C.I.75620;C.I. Natural Brown 1;Cotinin;Fisetholz;Fustel;Fustet;Junger Fustik;NSC 407010;NSC 656275;Superfustel;Superfustel K;Ungarisches Gelbholz;Ventin Sumach;Viset;Young Fustic;Young FusticCrystals;Zante Fustic;
  • PSA 111.13000
  • LogP 2.28240

Synthetic route

2-(3,4-dimethoxyphenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one
58544-90-4

2-(3,4-dimethoxyphenyl)-3-hydroxy-7-methoxy-4H-chromen-4-one

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 20℃; for 48h; Inert atmosphere;100%
With trimethylsilyl iodide In methanol at 35℃; for 96h; Inert atmosphere;
3,4,2',4'-tetrahydroxy-chalcone
487-52-5, 21849-70-7

3,4,2',4'-tetrahydroxy-chalcone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With sodium carbonate / sodium bicarbonate buffer solution; potassium hydrogen sulfate complex In dichloromethane; acetone at 20℃; for 21h;96.7%
3,3′,4′,7-tetraacetoxyflavone
114840-33-4

3,3′,4′,7-tetraacetoxyflavone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With sodium dithionite; water; sodium hydroxide In methanol at 20℃; for 4h; Inert atmosphere;65%
Fisetin 3',4'-dimethyl ether
93322-61-3

Fisetin 3',4'-dimethyl ether

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride
3,7,3',4'-tetrahydroxyflavanone
4382-36-9, 6514-92-7, 17654-28-3, 20725-03-5, 101849-13-2

3,7,3',4'-tetrahydroxyflavanone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With pyridine; air for 20h; Heating;
3.3'.4'-trimethoxy-7-acetoxy-flavone

3.3'.4'-trimethoxy-7-acetoxy-flavone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide
fisetin-3'.4'-dimethyl ether-7-ethyl ether

fisetin-3'.4'-dimethyl ether-7-ethyl ether

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide
fisetin-7.3'.4'-trimethyl ether-3-acetate

fisetin-7.3'.4'-trimethyl ether-3-acetate

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide
fisetin-7.3'.4'-trimethyl ether

fisetin-7.3'.4'-trimethyl ether

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With hydrogen iodide
2-(3,4-dimethoxy-phenyl)-3-hydroxy-7-methoxymethoxy-chromen-4-one
109688-49-5

2-(3,4-dimethoxy-phenyl)-3-hydroxy-7-methoxymethoxy-chromen-4-one

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; aqueous sulfuric acid
2: acetic acid anhydride; aqueous hydriodic acid
View Scheme
L-tyrosine
60-18-4

L-tyrosine

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 48h; Reagent/catalyst; Microbiological reaction;
L-tyrosine
60-18-4

L-tyrosine

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl β-D-thiogalactopyranoside / 24 h / 30 °C / Microbiological reaction
2: isopropyl β-D-thiogalactopyranoside / 3 h / 30 °C / Microbiological reaction
View Scheme
Multi-step reaction with 3 steps
1: isopropyl β-D-thiogalactopyranoside / 24 h / 30 °C / Microbiological reaction
2: isopropyl β-D-thiogalactopyranoside / 30 °C / Microbiological reaction
3: isopropyl β-D-thiogalactopyranoside / 18 h / 30 °C / Microbiological reaction
View Scheme
liquiritigenin
578-86-9

liquiritigenin

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 3h; Reagent/catalyst; Time; Microbiological reaction;
resokaempferol
2034-65-3

resokaempferol

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
With isopropyl β-D-thiogalactopyranoside at 30℃; for 18h; Reagent/catalyst; Time; Microbiological reaction;
2'-hydroxy-3,4,4'-trimethoxychalcone
57601-14-6

2'-hydroxy-3,4,4'-trimethoxychalcone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C
2: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
1-(2-hydroxy-4-methoxyphenyl)ethanone
552-41-0

1-(2-hydroxy-4-methoxyphenyl)ethanone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / ethanol / 20 °C
2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C
3: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / ethanol / 20 °C
2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 20 °C
3: boron tribromide / dichloromethane / 48 h / 20 °C / Inert atmosphere
View Scheme
quercetol
117-39-5

quercetol

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / 3 h / 80 °C
2: boron trifluoride diethyl etherate / 1,4-dioxane / 6 h / 80 °C
3: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4: Pd(OH)2/C, 20%; triethylamine; hydrogen / tetrahydrofuran / 1 h / 20 °C
5: sodium dithionite; sodium hydroxide; water / methanol / 4 h / 20 °C / Inert atmosphere
View Scheme
3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one
1064-06-8

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: boron trifluoride diethyl etherate / 1,4-dioxane / 6 h / 80 °C
2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3: Pd(OH)2/C, 20%; triethylamine; hydrogen / tetrahydrofuran / 1 h / 20 °C
4: sodium dithionite; sodium hydroxide; water / methanol / 4 h / 20 °C / Inert atmosphere
View Scheme
4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate
7251-37-8

4-(3,7-diacetoxy-5-hydroxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: Pd(OH)2/C, 20%; triethylamine; hydrogen / tetrahydrofuran / 1 h / 20 °C
3: sodium dithionite; sodium hydroxide; water / methanol / 4 h / 20 °C / Inert atmosphere
View Scheme
3,3′,4′,7-tetraacetoxy-5-triuoromethylsufonyloxyflavone

3,3′,4′,7-tetraacetoxy-5-triuoromethylsufonyloxyflavone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd(OH)2/C, 20%; triethylamine; hydrogen / tetrahydrofuran / 1 h / 20 °C
2: sodium dithionite; sodium hydroxide; water / methanol / 4 h / 20 °C / Inert atmosphere
View Scheme
2',4'-dihydroxy-4-acetophenone
89-84-9

2',4'-dihydroxy-4-acetophenone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / butanone / 12 h / Reflux
2: potassium hydroxide / ethanol / 20 h / Reflux; Inert atmosphere
3: palladium on activated charcoal; hydrogen / ethyl acetate
4: sodium carbonate / sodium bicarbonate buffer solution; potassium hydrogen sulfate complex / dichloromethane; acetone / 21 h / 20 °C
View Scheme
2,4-bis(benzyloxy)acetophenone
22877-01-6

2,4-bis(benzyloxy)acetophenone

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / ethanol / 20 h / Reflux; Inert atmosphere
2: palladium on activated charcoal; hydrogen / ethyl acetate
3: sodium carbonate / sodium bicarbonate buffer solution; potassium hydrogen sulfate complex / dichloromethane; acetone / 21 h / 20 °C
View Scheme
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

3,7-dihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-8-D

3,7-dihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-8-D

Conditions
ConditionsYield
With boron trifluoride; [D3]phosphoric acid In water-d2 at 55℃; for 24h; deuteration;78%
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

UDP-glucuronic acid
2616-64-0

UDP-glucuronic acid

Fisetin 7-O-glucuronide

Fisetin 7-O-glucuronide

Conditions
ConditionsYield
With UGT88D4 In aq. buffer at 30℃; for 12h; Reagent/catalyst; Solvent; Enzymatic reaction;68%
ethanol
64-17-5

ethanol

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

nicotinamide
98-92-0

nicotinamide

C15H10O6*2C6H6N2O*0.5C2H6O

C15H10O6*2C6H6N2O*0.5C2H6O

Conditions
ConditionsYield
at 20℃;58%
for 24h;
...Expand
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

2-(bromomethyl)-3,5,6-trimethylpyrazine
79074-45-6

2-(bromomethyl)-3,5,6-trimethylpyrazine

2-(3,4-bis((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)-3,7-bis((3,5,6-trimethylpyrazin-2-yl)-methoxy)-4H-chromen-4-one

2-(3,4-bis((3,5,6-trimethylpyrazin-2-yl)methoxy)phenyl)-3,7-bis((3,5,6-trimethylpyrazin-2-yl)-methoxy)-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide; acetone for 2h; Inert atmosphere;48%
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 2h; Inert atmosphere;48%
coniferal alcohol
458-35-5, 32811-40-8, 69056-21-9

coniferal alcohol

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

5-deoxy-3-hydroxyhydnocarpin-D

5-deoxy-3-hydroxyhydnocarpin-D

Conditions
ConditionsYield
With silver carbonate In acetone; benzene at 60℃; for 36h;27%
isonicotinamide
1453-82-3

isonicotinamide

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

C15H10O6*C6H6N2O

C15H10O6*C6H6N2O

Conditions
ConditionsYield
In methanol at 20℃;20%
In methanol for 24h; Solvent;
diazomethane
186581-53-3, 908094-01-9

diazomethane

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

3,3',4',7-tetra-O-methylfisetin
17093-86-6

3,3',4',7-tetra-O-methylfisetin

Conditions
ConditionsYield
Yield given;
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

acetic anhydride
108-24-7

acetic anhydride

3,3′,4′,7-tetraacetoxyflavone
114840-33-4

3,3′,4′,7-tetraacetoxyflavone

Conditions
ConditionsYield
With pyridine9 mg
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

dimethyl sulfate
77-78-1

dimethyl sulfate

3,3',4',7-tetra-O-methylfisetin
17093-86-6

3,3',4',7-tetra-O-methylfisetin

Conditions
ConditionsYield
With potassium carbonate
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

4-hydroxysalicylic acid
89-86-1

4-hydroxysalicylic acid

Conditions
ConditionsYield
With 18-crown-6 ether In tetrahydrofuran; toluene Product distribution; -10 deg C, then room temp.;
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

fisetin radical

fisetin radical

Conditions
ConditionsYield
With singlet oxygen In water at 20℃; Rate constant;
With 2,6-di-tert-butyl-α-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-tolyloxyl In ethanol at 20℃; Kinetics;
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

fisetin radical

fisetin radical

Conditions
ConditionsYield
With Ph2CHOO radical In chlorobenzene at 50℃; Rate constant;
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

methyl iodide
74-88-4

methyl iodide

potassium hydroxide

potassium hydroxide

methanol
67-56-1

methanol

...Expand
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

potash

potash

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
Beim Schmelzen;
...Expand
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

nitric acid
7697-37-2

nitric acid

A

oxalic acid
144-62-7

oxalic acid

B

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

...Expand
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

alkali

alkali

A

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

B

recorcinol
108-46-3

recorcinol

Conditions
ConditionsYield
Bei Einw. von Luft;
...Expand
3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

metaboric acid
13460-50-9

metaboric acid

oxalic acid
144-62-7

oxalic acid

acetic acid
64-19-7

acetic acid

compound C17H9BO10

compound C17H9BO10

...Expand
sulfuric acid
7664-93-9

sulfuric acid

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

fisetinsulfonic acid-(x)

fisetinsulfonic acid-(x)

diazomethane
186581-53-3, 908094-01-9

diazomethane

3,7,3',4'-tetrahydroxyflavone
528-48-3

3,7,3',4'-tetrahydroxyflavone

fisetintetramethyl ether

fisetintetramethyl ether

Fisetin Consensus Reports

Fisetin(528-48-3) is reported in EPA TSCA Inventory.

Fisetin Specification

The Fisetin, with the CAS registry number 528-48-3, has the IUPAC name of 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one. For being a kind of ochre powder, its product categories are including Flavanols; Biochemistry; Flavonoids.
         
The physical properties of this chemical are as below: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.5; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 46.13; (6)ACD/BCF (pH 7.4): 11; (7)ACD/KOC (pH 5.5): 534.08; (8)ACD/KOC (pH 7.4): 127.35; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.22; (13)Index of Refraction: 1.784; (14)Molar Refractivity: 71.43 cm3; (15)Molar Volume: 169.5 cm3; (16)Polarizability: 28.32 ×10-24 cm3; (17)Surface Tension: 98.9 dyne/cm; (18)Density: 1.688 g/cm3; (19)Flash Point: 233 °C; (20)Enthalpy of Vaporization: 93.84 kJ/mol; (21)Boiling Point: 599.4 °C at 760 mmHg; (22)Vapour Pressure: 3.23E-15 mmHg at 25°C; (23)Exact Mass: 286.047738; (24)MonoIsotopic Mass: 286.047738; (25)Topological Polar Surface Area: 107; (26)Heavy Atom Count: 21; (27)Complexity: 459.

Use of this chemical: 2-(3,4-dihydroxy-phenyl)-3,7-dihydroxy-chromen-4-one could react to produce 3,7-dihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-8-D. This reaction could happen in the presence of the reagent of D3PO4 & BF3 , and the solvent of D2O, and it needs the reaction time of 1 day and the reaction temperature of 55 ℃ with its yield of 78 %.

When you are dealing with this chemical, you should be careful. This is irritating to eyes, respiratory system and skin, so you should avoid contacting with skin and eyes and then do not breathe dust.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
(2)InChI: InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
(3)InChIKey: XHEFDIBZLJXQHF-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01998,

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