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491-70-3

Basic Information
CAS No.: 491-70-3
Name: Luteolin
Article Data: 100
Cas Database
Molecular Structure:
Molecular Structure of 491-70-3 (Luteolin)
Formula: C15H10O6
Molecular Weight: 286.241
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;
EINECS: 207-741-0
Density: 1.654 g/cm3
Melting Point: ~330 °C(lit.)
Boiling Point: 616.1 °C at 760 mmHg
Flash Point: 239.5 °C
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.
Appearance: yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-36/37/39
Transport Information: N/A
PSA: 111.13000
LogP: 2.28240
Synthetic route
520-36-5

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

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;
855-97-0

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

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%
58124-13-3

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

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

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%
14917-41-0

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

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%
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

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
5373-11-5, 68321-11-9

luteolin 7-O-glucoside

A

50-99-7

D-glucose

B

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

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%
491-70-3

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

Conditions
ConditionsYield
With sulfuric acid; water for 2h; Heating;50%
480-40-0

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

A

520-36-5

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

B

491-70-3

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

C

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%
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Chemistry

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

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.

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.

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

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.