3,5,7-trimethoxyflavone
galangin
Conditions | Yield |
---|---|
Stage #1: 3,5,7-trimethoxyflavone With boron tribromide In dichloromethane at 20℃; for 24h; Stage #2: With water In dichloromethane | 83% |
galangin
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; dichloromethane under 760.051 Torr; for 6h; | 73% |
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit Natronlauge; |
2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone
benzoic acid anhydride
galangin
Conditions | Yield |
---|---|
With sodium benzoate at 165 - 170℃; Verseifen des Reaktionsprodukts mit alkoh. Kalilauge; |
3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
galangin
Conditions | Yield |
---|---|
With air; methylene blue In methanol for 81h; Irradiation; | 54 % Turnov. |
galanginin - 3,5,7-trihydroxyflavone 3-O-β-D-glucopyranoside
galangin
Conditions | Yield |
---|---|
With water; hydrogen cation |
N,N,N',N'-tetramethyl-para-phenylenediamine
A
galangin
B
N,N,N',N'-tetramethyl-para-semiquinonediimine
Conditions | Yield |
---|---|
at 20℃; Equilibrium constant; pH=13.5; | |
at 20℃; Rate constant; Equilibrium constant; pH=13.5; |
galangin
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 2.3 mg |
galangin
Conditions | Yield |
---|---|
With sulfuric acid for 1h; Heating; | 3.2 mg |
galangin
Conditions | Yield |
---|---|
With hydrogen iodide |
galangin
Conditions | Yield |
---|---|
With ethanol; iodine; sodium acetate |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
With palladium on carbon In methanol; dichloromethane |
Conditions | Yield |
---|---|
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 |
1-(2-hydroxy-4,6-dimethoxy-phenyl)-2-methoxy-3-phenyl-1,3-propanedione
galangin
Conditions | Yield |
---|---|
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 |
C18H18O6
galangin
Conditions | Yield |
---|---|
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 |
2'-hydroxy-2,4',6'-trimethoxyacetophenone
galangin
Conditions | Yield |
---|---|
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 |
2-acetyl-3,5-bis(benzyloxy)phenyl benzoate
galangin
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
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 |
1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone
galangin
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
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 |
galangin
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide for 0.166667h; | 87% |
With pyridine at 20℃; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Heating; | 67% |
With potassium carbonate | |
With potassium carbonate In acetone for 4h; Heating; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Ambient temperature; | 64% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 63% |
Conditions | Yield |
---|---|
With TcCGT1-C-glycosyltransferase from Trolliuschinensisuridine in complex with uridine diphosphate In aq. phosphate buffer; dimethyl sulfoxide pH=8; Enzymatic reaction; | 61.5% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Ambient temperature; | 29% |
Conditions | Yield |
---|---|
With potassium superoxide; tetraethylammonium bromide In N,N-dimethyl-formamide at 20℃; for 16.5h; | 27% |
Conditions | Yield |
---|---|
With tetraethylammonium iodide In various solvent(s) at 20℃; for 1.5h; | 14% |
galangin
sodium methylate
5,7-dihydroxy-3-methoxy-6-methyl-2-phenyl-chromen-4-one
Conditions | Yield |
---|---|
With methanol anschliessendes Erwaermen mit Methyljodid; |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; acetone |
Conditions | Yield |
---|---|
With ethanol; sodium carbonate |
methanol
galangin
sodium methylate
methyl iodide
A
5,7-dihydroxy-3-methoxy-6-methyl-2-phenyl-chromen-4-one
B
5-hydroxy-3,7-dimethoxyflavone
C
5-hydroxy-3,7-dimethoxy-6-methyl-2-phenyl-chromen-4-one
D
3,5,7-trimethoxyflavone
galangin
A
isalpinin
B
5-hydroxy-3,7-dimethoxyflavone
C
5,7-dihydroxy-3-methoxyflavone
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With 18-crown-6 ether In tetrahydrofuran; toluene Product distribution; -10 deg C, then room temp.; |
galangin
Conditions | Yield |
---|---|
With singlet oxygen In water at 20℃; Rate constant; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 12 mg |
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. |
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