Product Name

  • Name

    Luteolin

  • EINECS 207-741-0
  • CAS No. 491-70-3
  • Article Data100
  • CAS DataBase
  • Density 1.654 g/cm3
  • Solubility Soluble in aqueous alkaline solutions (1.4 mg/ml), ethanol (~5 mg/ml), dimethyl sulfoxide (7 mg/ml), 1eq. Sodium hydroxide (5 mM), dimethylformamide (~20 mg/ml), water (1 mg/ml) at 25°C and methanol.
  • Melting Point ~330 °C(lit.)
  • Formula C15H10O6
  • Boiling Point 616.1 °C at 760 mmHg
  • Molecular Weight 286.241
  • Flash Point 239.5 °C
  • Transport Information
  • Appearance yellow crystalline powder
  • Safety 26-36-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 491-70-3 (Luteolin)
  • Hazard Symbols IrritantXi
  • Synonyms 4H-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-;Cyanidenon 1470;Prestwick_122;Flacitran;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy- (9CI);2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-benzopyrone;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-;3,4,5,7-Tetrahydroxyflavone;5,7,3,4-Tetrahydroxyflavone;C.I. Natural Yellow 2;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one;C.I. 75590;Luteolol;Digitoflavone;3',4',5,7-Tetrahydroxyflavone;
  • PSA 111.13000
  • LogP 2.28240

Synthetic route

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
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
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
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
58124-13-3

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

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In N,N-dimethyl-formamide Ambient temperature;80%
1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

1-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-(2,4,6-trihydroxy-phenyl)-propane-1,3-dione

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid In acetic acid at 95 - 100℃; for 1h;78%
2',3,4,4',6'-pentahydroxychalcone
14917-41-0

2',3,4,4',6'-pentahydroxychalcone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With oxygen at 20℃; under 760.051 Torr; for 1h; Reagent/catalyst;72%
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid for 4h;68.2%
With acid
With sulfuric acid; water for 2h; Heating;70 mg
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

D-glucose
50-99-7

D-glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With water Acidic conditions;A n/a
B 66%
Acid hydrolysis;
Acidic aq. solution;
Acidic conditions;
4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone

4,6-bis(methoxymethyl)-2-(3,4-diacetoxybenzoyloxy)acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
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%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With sulfuric acid; water for 2h; Heating;50%
5,7-dihydroxy-2-phenyl-chromen-4-one
480-40-0

5,7-dihydroxy-2-phenyl-chromen-4-one

A

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C

luteolin 3'-monosulphate

luteolin 3'-monosulphate

Conditions
ConditionsYield
With Mucore ramannianus (ATCC 9628) In N,N-dimethyl-formamide for 336h; Microbiological reaction;A 3%
B 10.2%
C 10.2%
6-bromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

6-bromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With water; hydrogen iodide; acetic anhydride
diosmetin
520-34-3

diosmetin

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With pyridine hydrochloride at 170℃; for 2h;
luteolin 7-O-<β-D-glucuronosyl(1-2)β-D-glucuronide>-4'-O-β-D-glucuronide

luteolin 7-O-<β-D-glucuronosyl(1-2)β-D-glucuronide>-4'-O-β-D-glucuronide

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C

luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide>

luteolin 7-O-<β-D-glucuronosyl(1<*>2)β-D-glucuronide>

Conditions
ConditionsYield
With formic acid In water at 100℃; for 3h; Product distribution; also enzymatic hydrolysis;
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

D-Glucose
2280-44-6

D-Glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid for 6h;
luteolin 7-O-glucoside
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

β-D-glucose
492-61-5

β-D-glucose

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
Product distribution; Acid hydrolysis;
luteolin-5-O-β-D-glucopyranoside
20344-46-1

luteolin-5-O-β-D-glucopyranoside

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With malic acid at 60℃; other object of study: half-lives; other reagent : acetic acid, oxalic acid, HCl; other temperature;
7-O-lactoyl-luteolin
126394-95-4

7-O-lactoyl-luteolin

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride In methanol at 100℃; for 7h; Product distribution;
luteolin 7-O-<2-O-β-glucopyranosyl-lactate>

luteolin 7-O-<2-O-β-glucopyranosyl-lactate>

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

D-Glucose
2280-44-6

D-Glucose

C

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst;
Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 7h; Product distribution; other time; reaction in the presence of catalyst;
(3',4'-dibenzyloxy-5,7-dimethoxymethyl)flavone
169132-97-2

(3',4'-dibenzyloxy-5,7-dimethoxymethyl)flavone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
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
3-<3,4-di(tert-butyldimethylsilyloxy)phenyl>-5-(2,4,6-trihydroxyphenyl)isoxazole

3-<3,4-di(tert-butyldimethylsilyloxy)phenyl>-5-(2,4,6-trihydroxyphenyl)isoxazole

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; boric acid; acetic acid; nickel 1.) dioxane-water, 2.) 2 h, reflux; Yield given. Multistep reaction;
2.4.6-trimethoxy-ω-<3.4-dimethoxy-benzoyl>-acetophenone

2.4.6-trimethoxy-ω-<3.4-dimethoxy-benzoyl>-acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen iodide
2.4.6-trimethoxy-ω-<3.4-methylenedioxy-benzoyl>-acetophenone

2.4.6-trimethoxy-ω-<3.4-methylenedioxy-benzoyl>-acetophenone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
With hydrogen iodide
diosmetin
520-34-3

diosmetin

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one
10544-05-5

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

3',4'-methylenedioxy-5,7-dimethoxyflavone
89029-12-9

3',4'-methylenedioxy-5,7-dimethoxyflavone

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

6,8-dibromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

6,8-dibromo-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chromen-4-one

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

5,7-diethoxy-2-(3,4-diethoxy-phenyl)-chromen-4-one
6169-14-8

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

hydrogen iodide
10034-85-2

hydrogen iodide

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

hydrogen iodide
10034-85-2

hydrogen iodide

chrysoeriol tri-O-acetate
3162-04-7

chrysoeriol tri-O-acetate

acetic acid
64-19-7

acetic acid

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

chlorosulfuric acid 2,2,2-trichloroethyl ester
764-09-0

chlorosulfuric acid 2,2,2-trichloroethyl ester

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H14Cl12O18S4

C23H14Cl12O18S4

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃;95%
furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C20H13NO7

C20H13NO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water pH=9.2; Reflux;95%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

acetic anhydride
108-24-7

acetic anhydride

luteolin tetraacetate
1061-93-4

luteolin tetraacetate

Conditions
ConditionsYield
With pyridine Reflux;92%
With sodium acetate
In pyridine Ambient temperature;49 mg
TFE*OTf
1269657-45-5

TFE*OTf

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H18Cl12O18S4
1313434-36-4

C23H18Cl12O18S4

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h;92%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2-(2-Aminoethoxy)ethanol
929-06-6

2-(2-Aminoethoxy)ethanol

C19H17NO8

C19H17NO8

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 65℃; pH=9.2;92%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

C31H46O18P4
1266147-86-7

C31H46O18P4

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux;90.7%
With potassium carbonate; acetone
2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate
1185733-70-3

2,2,2-trichloroethoxysulfuryl 2-methyl-3-methylimidazolium triflate

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C23H18Cl12O18S4
1313434-36-4

C23H18Cl12O18S4

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 0.366667h;90%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

(1S,2R,4aS,6aR,6bR,8aR,12aR,12bR,14bS)-6a-Hydroxymethyl-1,2,6b,9,9,12a-hexamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

(1S,2R,4aS,6aR,6bR,8aR,12aR,12bR,14bS)-6a-Hydroxymethyl-1,2,6b,9,9,12a-hexamethyl-10-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

Conditions
ConditionsYield
In methanol for 0.5h; Ambient temperature;88%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

L-proline
147-85-3

L-proline

luteolin L-proline cocrystals (1:1)

luteolin L-proline cocrystals (1:1)

Conditions
ConditionsYield
In ethanol; acetonitrile at 50℃;86.3%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Hexanoyl chloride
142-61-0

Hexanoyl chloride

5,7,3',4'-tetra-O-hexanoyl-luteolin

5,7,3',4'-tetra-O-hexanoyl-luteolin

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

methyl iodide
74-88-4

methyl iodide

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one
855-97-0

2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;84%
Dichlorodiphenylmethane
2051-90-3

Dichlorodiphenylmethane

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

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
1201808-21-0

2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4H-1-benzopyran-4-one

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

A

C15H9O9S(1-)*K(1+)
120537-30-6

C15H9O9S(1-)*K(1+)

B

C15H8O12S2(2-)*2K(1+)
116097-10-0

C15H8O12S2(2-)*2K(1+)

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

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

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

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethylene dibromide
106-93-4

ethylene dibromide

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dihydroxy-4H-chromen-4-one
445408-53-7

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5,7-dihydroxy-4H-chromen-4-one

Conditions
ConditionsYield
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%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethanolamine
141-43-5

ethanolamine

C17H13NO7

C17H13NO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 65℃; pH=9.2;78%
propylamine
107-10-8

propylamine

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C18H15NO6

C18H15NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2;76%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

dimethyl sulfate
77-78-1

dimethyl sulfate

pilloin
32174-62-2

pilloin

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Reflux;73%
With potassium carbonate In N,N-dimethyl-formamide at 60 - 65℃; for 3h;20.9%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

ethylamine
75-04-7

ethylamine

C17H13NO6

C17H13NO6

Conditions
ConditionsYield
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
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

benzyl bromide
100-39-0

benzyl bromide

7-(benzyloxy)-2-(3',4'-bis(benzyloxy)phenyl)-5-hydroxy-4H-chromen-4-one
1201807-92-2

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

Conditions
ConditionsYield
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%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

benzylamine
100-46-9

benzylamine

C22H15NO6

C22H15NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2; Sonication;70.1%
SEC-BUTYLAMINE
33966-50-6

SEC-BUTYLAMINE

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

C19H17NO6

C19H17NO6

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 50℃; pH=9.2;68%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

allyl bromide
106-95-6

allyl bromide

C27H26O6

C27H26O6

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h; Reflux;67.6%

Luteolin Chemical Properties

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 Uses

 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.

Luteolin Toxicity Data With Reference

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.

Luteolin Safety Profile

A poison by intraperitoneal route. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: IrritantXi
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 Specification

 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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