5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With C9H8IO4Pol In dimethyl sulfoxide at 25℃; for 2h; | 95% |
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction; |
2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With pyridine hydrochloride at 190℃; for 6h; Inert atmosphere; | 89% |
With pyridine hydrochloride at 180℃; for 6.5h; Inert atmosphere; | 88% |
Stage #1: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one With aluminum (III) chloride In toluene at 80 - 140℃; Stage #2: With hydrogenchloride In water; toluene at 0℃; Reagent/catalyst; Solvent; Temperature; Time; | 70.2% |
2-(3,4-bis(benzyloxy)phenyl)-5,7-dihydroxy-4H-chromen-4-one
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide Ambient temperature; | 80% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid at 95 - 100℃; for 1h; | 78% |
2',3,4,4',6'-pentahydroxychalcone
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With oxygen at 20℃; under 760.051 Torr; for 1h; Reagent/catalyst; | 72% |
luteolin 7-O-glucoside
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With sulfuric acid for 4h; | 68.2% |
With acid | |
With sulfuric acid; water for 2h; Heating; | 70 mg |
luteolin 7-O-glucoside
A
D-glucose
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With water Acidic conditions; | A n/a B 66% |
Acid hydrolysis; | |
Acidic aq. solution; | |
Acidic conditions; |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
Stage #1: 4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone With potassium hydroxide In pyridine at 50℃; for 0.333333h; Stage #2: With acetic acid In pyridine; water for 0.5h; Stage #3: With hydrogenchloride In methanol Reflux; | 55% |
scolymoside
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With sulfuric acid; water for 2h; Heating; | 50% |
5,7-dihydroxy-2-phenyl-chromen-4-one
A
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With Mucore ramannianus (ATCC 9628) In N,N-dimethyl-formamide for 336h; Microbiological reaction; | A 3% B 10.2% C 10.2% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With water; hydrogen iodide; acetic anhydride |
Conditions | Yield |
---|---|
With pyridine hydrochloride at 170℃; for 2h; |
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With formic acid In water at 100℃; for 3h; Product distribution; also enzymatic hydrolysis; |
luteolin 7-O-glucoside
A
D-Glucose
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride | |
With sulfuric acid for 6h; |
luteolin 7-O-glucoside
A
β-D-glucose
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
Product distribution; Acid hydrolysis; |
luteolin-5-O-β-D-glucopyranoside
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With malic acid at 60℃; other object of study: half-lives; other reagent : acetic acid, oxalic acid, HCl; other temperature; |
7-O-lactoyl-luteolin
A
LACTIC ACID
B
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 100℃; for 7h; Product distribution; |
A
LACTIC ACID
B
D-Glucose
C
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst; |
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst; |
(3',4'-dibenzyloxy-5,7-dimethoxymethyl)flavone
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | |
Multi-step reaction with 3 steps 1: 75 percent / HCl / ethanol; hexane / 1 h / Ambient temperature 2: 18percent HCl / ethanol / 0.5 h / Heating 3: 80 percent / H2 / Pd/C / dimethylformamide / Ambient temperature View Scheme |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; boric acid; acetic acid; nickel 1.) dioxane-water, 2.) 2 h, reflux; Yield given. Multistep reaction; |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide |
diosmetin
hydrogen iodide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one
hydrogen iodide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
3',4'-methylenedioxy-5,7-dimethoxyflavone
hydrogen iodide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
hydrogen iodide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
5,7-diethoxy-2-(3,4-diethoxy-phenyl)-chromen-4-one
hydrogen iodide
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
hydrogen iodide
chrysoeriol tri-O-acetate
acetic acid
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
chlorosulfuric acid 2,2,2-trichloroethyl ester
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water pH=9.2; Reflux; | 95% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
acetic anhydride
luteolin tetraacetate
Conditions | Yield |
---|---|
With pyridine Reflux; | 92% |
With sodium acetate | |
In pyridine Ambient temperature; | 49 mg |
TFE*OTf
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
C23H18Cl12O18S4
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h; | 92% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 65℃; pH=9.2; | 92% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
diethyl chlorophosphate
C31H46O18P4
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; for 24.5h; Inert atmosphere; Cooling with ice; | 91% |
With dmap; triethylamine In tetrahydrofuran at 70℃; for 3.5h; Cooling with ice; Inert atmosphere; |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
dimethyl sulfate
2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 10h; Reflux; | 90.7% |
With potassium carbonate; acetone |
2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
C23H18Cl12O18S4
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h; | 90% |
diazomethane
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
In methanol for 0.5h; Ambient temperature; | 88% |
Conditions | Yield |
---|---|
In ethanol; acetonitrile at 50℃; | 86.3% |
Conditions | Yield |
---|---|
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice; | 85% |
With dmap; triethylamine In N,N-dimethyl-formamide |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
methyl iodide
2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; | 84% |
Dichlorodiphenylmethane
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 180℃; for 1h; Inert atmosphere; Sealed tube; Microwave irradiation; | 83% |
In diphenylether at 165℃; for 2.5h; | 70% |
In diphenylether at 165℃; for 2.5h; | 70% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
A
C15H9O9S(1-)*K(1+)
B
C15H8O12S2(2-)*2K(1+)
Conditions | Yield |
---|---|
With potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide In pyridine at 4℃; for 72h; Yields of byproduct given; | A n/a B 78% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
Conditions | Yield |
---|---|
With boron trifluoride; [D3]phosphoric acid In water-d2 at 55℃; for 48h; deuteration; | 78% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
ethylene dibromide
2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dihydroxy-4H-chromen-4-one
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h; | 78% |
With potassium carbonate In dimethyl sulfoxide at 70℃; for 1h; | 32.4% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h; | 28.1% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 65℃; pH=9.2; | 78% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 50℃; pH=9.2; | 76% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
dimethyl sulfate
pilloin
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 1h; Reflux; | 73% |
With potassium carbonate In N,N-dimethyl-formamide at 60 - 65℃; for 3h; | 20.9% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water at 50℃; pH=9.2-9.3; | 72% |
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
benzyl bromide
7-(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)-5-hydroxy-4H-chromen-4-one
Conditions | Yield |
---|---|
Stage #1: 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; | 71% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; | 56% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 50℃; pH=9.2; Sonication; | 70.1% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 50℃; pH=9.2; | 68% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 10h; Reflux; | 67.6% |
Molecular Structure of Luteolin (CAS NO.491-70-3):
IUPAC Name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
Empirical Formula: C15H10O6
Molecular Weight: 286.2363
H bond acceptors: 6
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 63.22Å2
Index of Refraction: 1.767
Molar Refractivity: 71.73 cm3
Molar Volume: 172.9 cm3
Surface Tension: 92.5 dyne/cm
Density: 1.654 g/cm3
Flash Point: 239.5 °C
Enthalpy of Vaporization: 94.73 kJ/mol
Boiling Point: 616.1 °C at 760 mmHg
Vapour Pressure: 9.03E-16 mmHg at 25°C
Melting point: 330 oC
Storage temp: 2-8oC
EINECS: 207-741-0
Product Categories: Tetra-substituted Flavones; Natural Plant Extract; Inhibitors; Tyrosine Kinase Inhibitors; Cytokine signaling
InChI
InChI=1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
Smiles
c12c(c(cc(o1)c1cc(c(O)cc1)O)=O)c(cc(c2)O)O
Luteolin (CAS NO.491-70-3) is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an agent in the prevention of inflammation, a promoter of carbohydrate metabolism and an immune system modulator. Multiple research experiments describe luteolin as a biochemical agent that can dramatically reduce inflammation and the symptoms of septic shock.These characteristics of luteolin are also believed to play an important part in the prevention of cancer.
1. | mnt-hmn-lym 10 mg/L | MUREAV Mutation Research. 246 (1991),205. | ||
2. | sce-hmn-lym 10 mg/L | MUREAV Mutation Research. 246 (1991),205. | ||
3. | sln-hmn-lym 20 mg/L | MUREAV Mutation Research. 246 (1991),205. | ||
4. | ipr-mus LD50:180 mg/kg | YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. 16 (2)(1981),11. |
A poison by intraperitoneal route. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
RTECS: LK9275210
Luteolin , with CAS number of 491-70-3, can be called 3',4',5,7-Tetrahydroxyflavone ; 5,7,3',4'-Tetrahydroxyflavone ; Digitoflavone ; Luteoline ; Salifazide . Luteolin (CAS NO.491-70-3) is often found in leaves, but it is also seen in celery, thyme, dandelion, rinds, barks, clover blossom and ragweed pollen. Luteolin has also been isolated from Salvia tomentosa. Dietary sources include celery, green pepper, thyme, perilla and camomile tea.
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