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548-83-4

Basic Information
CAS No.: 548-83-4
Name: 4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-phenyl-
Molecular Structure:
Molecular Structure of 548-83-4 (4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2-phenyl-)
Formula: C15H10O5
Molecular Weight: 270.25
Synonyms: Flavone,3,5,7-trihydroxy- (7CI,8CI);Galangin (6CI);3,5,7-Trihydroxyflavone;NSC407229;Norizalpinin;
EINECS: 208-960-4
Density: 1.579 g/cm3
Melting Point: 214-215 °C(lit.)
Boiling Point: 518.6 °C at 760 mmHg
Flash Point: 202 °C
Solubility:
Appearance: Yellowish needle-like crystal
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 90.90000
LogP: 2.57680
Synthetic route
26964-29-4

3,5,7-trimethoxyflavone

548-83-4

galangin

Conditions
ConditionsYield
Stage #1: 3,5,7-trimethoxyflavone With boron tribromide In dichloromethane at 20℃; for 24h;
Stage #2: With water In dichloromethane
83%

5,7-bis(benzyloxy)-3-hydroxy-2-phenyl-4H-chromen-4-one

548-83-4

galangin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; dichloromethane under 760.051 Torr; for 6h;73%

2-benzoyloxy-1-(2,4,6-tris-benzoyloxy-phenyl)-ethanone

127-08-2

potassium acetate

108-24-7

acetic anhydride

548-83-4

galangin

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit Natronlauge;
65982-77-6

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

93-97-0

benzoic acid anhydride

548-83-4

galangin

Conditions
ConditionsYield
With sodium benzoate at 165 - 170℃; Verseifen des Reaktionsprodukts mit alkoh. Kalilauge;
82451-30-7, 4197-97-1

3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

548-83-4

galangin

Conditions
ConditionsYield
With air; methylene blue In methanol for 81h; Irradiation;54 % Turnov.
68592-14-3

galanginin - 3,5,7-trihydroxyflavone 3-O-β-D-glucopyranoside

548-83-4

galangin

Conditions
ConditionsYield
With water; hydrogen cation
100-22-1

N,N,N',N'-tetramethyl-para-phenylenediamine

galangin radical

A

548-83-4

galangin

B

100-22-1

N,N,N',N'-tetramethyl-para-semiquinonediimine

Conditions
ConditionsYield
at 20℃; Equilibrium constant; pH=13.5;
at 20℃; Rate constant; Equilibrium constant; pH=13.5;

galangin-8-sulfonate

548-83-4

galangin

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;2.3 mg

galangin-3-O-β-D-glucoside-8-sulfonate

548-83-4

galangin

Conditions
ConditionsYield
With sulfuric acid for 1h; Heating;3.2 mg
galangin-5.7-dimethyl ether

galangin-5.7-dimethyl ether

548-83-4

galangin

Conditions
ConditionsYield
With hydrogen iodide
pinobanksin

pinobanksin

548-83-4

galangin

Conditions
ConditionsYield
With ethanol; iodine; sodium acetate
480-66-0

2,4,6-trihydroxyacetophenone

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. KOH / ethanol / 48 h / Ambient temperature
2: 54 percent Turnov. / air, methylene blue / methanol / 81 h / Irradiation
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 73 h
2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C
3.1: tetrahydrofuran / 4 h / 0 - 20 °C
4.1: phosphonic acid diethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C
5.1: acetonitrile / 82 °C
6.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
7.1: sodium acetate / acetic acid / 12 h / 100 °C
8.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
8.2: Dowex 50W-X 8 resin / 20 °C
9.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme
100-52-7

benzaldehyde

aminoguanidine salt

aminoguanidine salt

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. KOH / ethanol / 48 h / Ambient temperature
2: 54 percent Turnov. / air, methylene blue / methanol / 81 h / Irradiation
View Scheme
108-73-6

3,5-dihydroxyphenol

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; hydrogen chloride / Kochen des Reaktionsprodukts mit Alkohol
2: sodium benzoate / 165 - 170 °C / Verseifen des Reaktionsprodukts mit alkoh. Kalilauge
View Scheme
Multi-step reaction with 10 steps
1.1: boron trifluoride diethyl etherate / 49 h / 0 - 20 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 73 h
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C
4.1: tetrahydrofuran / 4 h / 0 - 20 °C
5.1: phosphonic acid diethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C
6.1: acetonitrile / 82 °C
7.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
8.1: sodium acetate / acetic acid / 12 h / 100 °C
9.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
9.2: Dowex 50W-X 8 resin / 20 °C
10.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

C36H28O5

548-83-4

galangin

Conditions
ConditionsYield
With palladium on carbon In methanol; dichloromethane
500-99-2

3,5-dimethoxyphenol

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C
2: lithium diisopropyl amide / tetrahydrofuran
3: sulfuric acid; acetic acid / 0.5 h / 80 °C
4: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C
2: lithium diisopropyl amide / tetrahydrofuran
3: sulfuric acid; acetic acid / 0.5 h / 80 °C
4: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C
2: lithium diisopropyl amide / tetrahydrofuran
3: sulfuric acid; acetic acid / 0.5 h / 80 °C
4: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 1,1,2,2-tetrachloroethane / 20 °C
2: triethylamine / dichloromethane / 0 - 20 °C
3: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 - 0 °C / Inert atmosphere
4: sulfuric acid; acetic acid / 0.5 h / 80 °C
5: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
1385652-08-3

1-(2-hydroxy-4,6-dimethoxy-phenyl)-2-methoxy-3-phenyl-1,3-propanedione

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; acetic acid / 0.5 h / 80 °C
2: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
1385651-92-2

C18H18O6

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 - 0 °C / Inert atmosphere
2: sulfuric acid; acetic acid / 0.5 h / 80 °C
3: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
17874-42-9

2'-hydroxy-2,4',6'-trimethoxyacetophenone

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium diisopropyl amide / tetrahydrofuran
2: sulfuric acid; acetic acid / 0.5 h / 80 °C
3: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium diisopropyl amide / tetrahydrofuran
2: sulfuric acid; acetic acid / 0.5 h / 80 °C
3: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: lithium diisopropyl amide / tetrahydrofuran
2: sulfuric acid; acetic acid / 0.5 h / 80 °C
3: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: lithium diisopropyl amide / tetrahydrofuran / 1 h / -15 - 0 °C / Inert atmosphere
3: sulfuric acid; acetic acid / 0.5 h / 80 °C
4: boron tribromide / dichloromethane / 24 h / 20 °C
View Scheme
137790-51-3

2-acetyl-3,5-bis(benzyloxy)phenyl benzoate

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: tetrahydrofuran / 4 h / 0 - 20 °C
2.1: phosphonic acid diethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C
3.1: acetonitrile / 82 °C
4.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
5.1: sodium acetate / acetic acid / 12 h / 100 °C
6.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
6.2: Dowex 50W-X 8 resin / 20 °C
7.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

3,5-bis(benzyloxy)-2-(2-bromoacetyl)phenyl benzoate

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetonitrile / 82 °C
2.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
3.1: sodium acetate / acetic acid / 12 h / 100 °C
4.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
4.2: Dowex 50W-X 8 resin / 20 °C
5.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

2-(2-(benzoyloxy)-4,6-bis(benzyloxy)phenyl)-2-oxoethyl benzoate

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
2.1: sodium acetate / acetic acid / 12 h / 100 °C
3.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
3.2: Dowex 50W-X 8 resin / 20 °C
4.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme
18065-05-9

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 0 - 20 °C
2.1: tetrahydrofuran / 4 h / 0 - 20 °C
3.1: phosphonic acid diethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C
4.1: acetonitrile / 82 °C
5.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
6.1: sodium acetate / acetic acid / 12 h / 100 °C
7.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
7.2: Dowex 50W-X 8 resin / 20 °C
8.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

C29H22Br2O5

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: phosphonic acid diethyl ester; triethylamine / tetrahydrofuran / 0 - 20 °C
2.1: acetonitrile / 82 °C
3.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C
4.1: sodium acetate / acetic acid / 12 h / 100 °C
5.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
5.2: Dowex 50W-X 8 resin / 20 °C
6.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

C36H28O7

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium acetate / acetic acid / 12 h / 100 °C
2.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
2.2: Dowex 50W-X 8 resin / 20 °C
3.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme

C36H26O6

548-83-4

galangin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate / methanol; dichloromethane / 10 h / 20 °C
1.2: Dowex 50W-X 8 resin / 20 °C
2.1: palladium 10% on activated carbon; hydrogen / dichloromethane; tetrahydrofuran / 6 h / 760.05 Torr
View Scheme
548-83-4

galangin

108-24-7

acetic anhydride

113163-70-5

3,5,7-triacetoxyflavone

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide for 0.166667h;87%
With pyridine at 20℃;
548-83-4

galangin

77-78-1

dimethyl sulfate

26964-29-4

3,5,7-trimethoxyflavone

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Heating;67%
With potassium carbonate
With potassium carbonate In acetone for 4h; Heating;
74-96-4

ethyl bromide

548-83-4

galangin

MRS 1093

Conditions
ConditionsYield
With potassium carbonate In acetone Ambient temperature;64%
548-83-4

galangin

107-08-4

1-iodo-propane

MRS 1042

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;63%
548-83-4

galangin

952585-00-1

uridine-5'-diphosphoglucose

28225-12-9

galangin 8-C-β-D-glucoside

Conditions
ConditionsYield
With TcCGT1-C-glycosyltransferase from Trolliuschinensisuridine in complex with uridine diphosphate In aq. phosphate buffer; dimethyl sulfoxide pH=8; Enzymatic reaction;61.5%
548-83-4

galangin

107-30-2

chloromethyl methyl ether

143724-68-9

3,7-dimethoxymethylgalangin

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Ambient temperature;29%
548-83-4

galangin

83-30-7

acide 2,4,6-trihydroxybenzoique

Conditions
ConditionsYield
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 16.5h;27%
548-83-4

galangin

870-63-3

prenyl bromide

42193-83-9

8-prenylgalangin

Conditions
ConditionsYield
With tetraethylammonium iodide In various solvent(s) at 20℃; for 1.5h;14%
548-83-4

galangin

124-41-4

sodium methylate

93322-38-4

5,7-dihydroxy-3-methoxy-6-methyl-2-phenyl-chromen-4-one

Conditions
ConditionsYield
With methanol anschliessendes Erwaermen mit Methyljodid;
548-83-4

galangin

77-78-1

dimethyl sulfate

480-14-8

isalpinin

Conditions
ConditionsYield
With sodium hydrogencarbonate; acetone
548-83-4

galangin

77-78-1

dimethyl sulfate

6665-74-3

5,7-dihydroxy-3-methoxyflavone

Conditions
ConditionsYield
With ethanol; sodium carbonate
67-56-1

methanol

548-83-4

galangin

124-41-4

sodium methylate

74-88-4

methyl iodide

A

93322-38-4

5,7-dihydroxy-3-methoxy-6-methyl-2-phenyl-chromen-4-one

B

70786-48-0

5-hydroxy-3,7-dimethoxyflavone

C

727381-61-5

5-hydroxy-3,7-dimethoxy-6-methyl-2-phenyl-chromen-4-one

D

26964-29-4

3,5,7-trimethoxyflavone

548-83-4

galangin

A

480-14-8

isalpinin

B

70786-48-0

5-hydroxy-3,7-dimethoxyflavone

C

6665-74-3

5,7-dihydroxy-3-methoxyflavone

Conditions
ConditionsYield
With O-methyl transferase from cell-free extract of Citrus mitis; <(14)CH3>-S-adenosyl-L-methionine; 2-hydroxyethanethiol In water; dimethyl sulfoxide at 35℃; for 0.5h; Product distribution; pH 7.5 buffer;
548-83-4

galangin

A

487-70-7

2,4,6-trihydroxybenzaldehyde

B

65-85-0

benzoic acid

Conditions
ConditionsYield
With 18-crown-6 ether In tetrahydrofuran; toluene Product distribution; -10 deg C, then room temp.;
548-83-4

galangin

galangin radical

Conditions
ConditionsYield
With singlet oxygen In water at 20℃; Rate constant;
548-83-4

galangin

75-03-6

ethyl iodide

MRS 1041

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;12 mg
548-83-4

galangin

67-64-1

acetone

77-78-1

dimethyl sulfate

sodium hydrogencarbonate

sodium hydrogencarbonate

480-14-8

isalpinin

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Specification

The Galangin is an organic compound with the formula C15H10O5. The IUPAC name of this chemical is 3,5,7-trihydroxy-2-phenylchromen-4-one. With the CAS registry number 548-83-4, it is also named as 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-. The product's category is Flavanols. Besides, it should be stored in a closed and well-ventilated place.

Physical properties about Galangin are: (1)ACD/LogP: 2.83; (2)ACD/LogD (pH 5.5): 2.76; (3)ACD/LogD (pH 7.4): 1.49; (4)ACD/BCF (pH 5.5): 70.37; (5)ACD/BCF (pH 7.4): 3.85; (6)ACD/KOC (pH 5.5): 697.2; (7)ACD/KOC (pH 7.4): 38.12; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 53.99 Å2; (12)Index of Refraction: 1.747; (13)Molar Refractivity: 69.55 cm3; (14)Molar Volume: 171.1 cm3; (15)Polarizability: 27.57×10-24cm3; (16)Surface Tension: 84.9 dyne/cm; (17)Density: 1.579 g/cm3; (18)Flash Point: 202 °C; (19)Enthalpy of Vaporization: 82.11 kJ/mol; (20)Boiling Point: 518.6 °C at 760 mmHg; (21)Vapour Pressure: 2.24E-11 mmHg at 25°C.

Uses of Galangin: it can be used to produce 3,5,7-trimethoxy-2-phenyl-chromen-4-one. It will need reagent K2CO3.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O
(2)InChI: InChI=1/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
(3)InChIKey: VCCRNZQBSJXYJD-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
(5)Std. InChIKey: VCCRNZQBSJXYJD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD oral > 1500mg/kg (1500mg/kg)   Dokl Akad Nauk resp. Uzb.Vol. (9-10), Pg. 55, 1995.