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117-39-5

Basic Information
CAS No.: 117-39-5
Name: Quercetin
Molecular Structure:
Molecular Structure of 117-39-5 (Quercetin)
Formula: C15H10O7
Molecular Weight: 302.2357
Synonyms: 4H-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-;Quercetin content;Cyanidelonon 1522;3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on;3,5,7,3,4-Pentahydroxyflavone;Quercetine;Quercetol;3,3',4',5,7-pentahydroxyflavone;Quercetin 99%;Sophoretin;C.I. natural yellow 10 & 13;C.I. Natural Yellow 10;Quertin;C.I. 75670;Quertine;t-Gelb bzw. grun 1;3,4,5,7-Tetrahydroxyflavan-3-ol;4H-1-Benzopyran-4-one, 2- (3,4-dihydroxyphenyl)-3,5,7-trihydroxy-;Xanthaurine;3,5,7,3, 4-Pentahydroxyflavone;Flavin meletin;Flavone, 3,3,4,5,7-pentahydroxy-;2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one;Flavone, 3,4,5,5,7-pentahydroxy-;3,3,4,5,7-Pentahydroxyflavone;2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chromen-4-one;
EINECS: 204-187-1
Density: 1.799 g/cm3
Melting Point: 314-317 ºC
Boiling Point: 642.4 ºC at 760 mmHg
Flash Point: 248.1 ºC
Solubility: <0.1 g/100 mL at 21 ºC in water
Appearance: Yellow to green yellow crystalline powde
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-36/37/38
Safety: 45-36-26
Transport Information:
PSA: 131.36000
LogP: 1.98800
Synthetic route
117-39-5

quercetol

Conditions
ConditionsYield
With hydrogenchloride; methanol for 3h; Heating;96%
With water at 100℃; Kinetics; Ionic liquid;90%
With sulfuric acid; water at 20℃; for 0.166667h;89%
7647-01-0

hydrogenchloride

187221-65-4

quercetin triphenylantimony complex

A

117-39-5

quercetol

B

594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

Conditions
ConditionsYield
heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene;A 75%
B 88%
95412-48-9

6,8-dibromoquercetin

117-39-5

quercetol

Conditions
ConditionsYield
With sodium sulfite In water at 60℃; for 18h; Green chemistry;87%
1244-78-6

2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone

117-39-5

quercetol

Conditions
ConditionsYield
With boron tribromide In dichloromethane for 6h; Heating;83%
With trimethylsilyl iodide In methanol at 35℃; for 96h; Inert atmosphere;
482-36-0

Hyperoside

A

10257-28-0

D-Galactose

B

117-39-5

quercetol

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 1h;A n/a
B 68%
With grape snail enzymes
With rhamnodiastase

antoside

A

2280-44-6

D-Glucose

B

73-34-7

L-rhamnose

C

117-39-5

quercetol

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 2h;A n/a
B n/a
C 68%
With sulfuric acid at 100℃; for 2h;A n/a
B n/a
C 47%
491-50-9, 36450-05-2, 59985-52-3

quercetin 7-O-β-D-glucopyranoside

117-39-5

quercetol

Conditions
ConditionsYield
Acid hydrolysis;68%
With sulfuric acid for 1h; Heating;
491-50-9, 36450-05-2, 59985-52-3

quercetin 7-O-β-D-glucopyranoside

A

50-99-7

D-glucose

B

117-39-5

quercetol

Conditions
ConditionsYield
With water Acidic conditions;A n/a
B 65%
With water Acidic conditions;
482-35-9

isoquercetin

A

2280-44-6

D-Glucose

B

117-39-5

quercetol

Conditions
ConditionsYield
With sulfuric acidA n/a
B 64.3%
Product distribution; object of study - products of acid hydrolysis;
With 2M HCl In hydrogenchloride at 90℃; for 1h; Product distribution; other reagent;
482-36-0

Hyperoside

A

59-23-4

D-Galactose

B

117-39-5

quercetol

Conditions
ConditionsYield
With water Acidic conditions;A n/a
B 64%
Acidic conditions;
Acidic aq. solution;
482-35-9

isoquercetin

117-39-5

quercetol

Conditions
ConditionsYield
Acidic conditions;63.3%
With oxonium
With hydrogenchloride; ethanol for 4h; Heating;
482-36-0

Hyperoside

117-39-5

quercetol

Conditions
ConditionsYield
Acidic conditions;63.3%
Acid hydrolysis;
With hydrogenchloride In water for 0.5h; Reflux;
Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger K2 in Pichia pastoris In aq. phosphate buffer; dimethyl sulfoxide at 35 - 100℃; for 24h; pH=5; Enzymatic reaction;A 63%
B n/a
With rhamnodiastase Reactivity; Enzymatic reaction;
With rutinosidase In water Enzymatic reaction;
458-35-5

coniferol

A

C22H32O12

B

117-39-5

quercetol

Conditions
ConditionsYield
With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger In dimethyl sulfoxide at 35℃; for 8h; pH=5; Enzymatic reaction;A 60%
B n/a
215257-15-1

3,3',4',5,7-pentahydroxy flavanone

117-39-5

quercetol

Conditions
ConditionsYield
With potassium pyrosulfite In ethanol at 100℃;50%
With pyridine; air for 20h; Heating;

A

3615-41-6

L-Rhamnose

B

50-99-7

D-glucose

C

117-39-5

quercetol

Conditions
ConditionsYield
With sulfuric acid; waterA n/a
B n/a
C 47%
With sulfuric acid
With hydrogenchloride; water In methanol at 100℃; for 2h;
492-00-2

3,7-dihydroxyflavone

616-38-6

carbonic acid dimethyl ester

117-39-5

quercetol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 72h;28%
Conditions
ConditionsYield
Stage #1: p-hydroxyphenethyl alcohol; rutin In methanol at 40℃; for 30h;
Stage #2: With water In methanol for 0.166667h; Reflux; regioselective reaction;
A n/a
B n/a
C 24%
603-61-2

tamarixetin

117-39-5

quercetol

Conditions
ConditionsYield
With water; hydrogen iodide; acetic anhydride at 150℃;
4382-17-6

3,3'-di-O-methylquercetin

117-39-5

quercetol

Conditions
ConditionsYield
With water; hydrogen iodide at 150℃;
859439-36-4

2-benzo[1,3]dioxol-5-yl-3-hydroxy-5,7-dimethoxy-chromen-4-one

117-39-5

quercetol

Conditions
ConditionsYield
With aluminium trichloride; chlorobenzene at 130℃; Erwaermen des Reaktionsgemisches mit wss. HCl;
90-19-7

rhamnetin

117-39-5

quercetol

572-30-5

avicularin

A

10323-20-3

D-Arabinose

B

117-39-5

quercetol

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;
482-35-9

isoquercetin

A

492-61-5

β-D-glucose

B

117-39-5

quercetol

Conditions
ConditionsYield
Product distribution; acid hydrolysis;
Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
117-39-5

quercetol

108-24-7

acetic anhydride

1064-06-8

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

Conditions
ConditionsYield
With pyridine at 130 - 140℃;100%
With pyridine at 140 - 145℃; for 4h;97.5%
With pyridine at 70℃; for 6h;95%
117-39-5

quercetol

C30H20O14Se

Conditions
ConditionsYield
With hydrogenchloride; selenium(IV) oxide In ethanol; water at 60℃; for 12h; Inert atmosphere;99.2%
117-39-5

quercetol

108-24-7

acetic anhydride

7622-90-4

quercetin-3',4',5,7-tetraacetate

Conditions
ConditionsYield
With magnesium In neat (no solvent) at 25℃; for 3.5h; Temperature;98%
117-39-5

quercetol

glucosidase

glucosidase

482-35-9

isoquercetin

Conditions
ConditionsYield
With 1% disodium hydrogen phosphate-sodium citrate; 35-40% glucosyltransferase at 40 - 45℃; Enzymatic reaction;97.2%
117-39-5

quercetol

98-88-4

benzoyl chloride

120036-90-0

2-(3,4-bis(benzoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tribenzoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;97%
With pyridine at 22 - 24℃; for 4h;92%
With pyridine at 60℃;56%
With sodium hydroxide
117-39-5

quercetol

97-72-3

2-Methylpropionic anhydride

102607-68-1

2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate)

Conditions
ConditionsYield
With pyridine for 2h; Reflux;97%
In pyridine Ambient temperature;0.43 g
117-39-5

quercetol

18162-48-6

tert-butyldimethylsilyl chloride

265975-30-2

3,3',4',5,7-penta-O-tert-butyldimethylsilylquercetin

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 6h; silylation;97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 5h;
117-39-5

quercetol

100-39-0

benzyl bromide

13157-90-9

2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 72h;95%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Etherification;89%
Stage #1: quercetol; benzyl bromide With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; for 15h;
Stage #2: With water In N,N-dimethyl-formamide at 20℃; for 1h;
80%
117-39-5

quercetol

100-44-7

benzyl chloride

13157-90-9

2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate at 20℃; for 35h; Inert atmosphere;95%
With tetrabutylammomium bromide; potassium carbonate In 1-methyl-pyrrolidin-2-one; acetone at 85 - 90℃; for 24h;93%
With potassium carbonate; Aethyl-dipropyl-benzyl-ammonium In N,N,N,N,N,N-hexamethylphosphoric triamide for 35h; Inert atmosphere;90%
With tetrabutylammomium bromide; potassium carbonate In 1-methyl-pyrrolidin-2-one; acetone at 75℃; for 24h; Inert atmosphere;87%
With potassium carbonate; N,N-dimethyl-formamide at 20℃; for 12h;15%
117-39-5

quercetol

127-09-3

sodium acetate

108-24-7

acetic anhydride

1064-06-8

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

Conditions
ConditionsYield
Reflux; Inert atmosphere;95%
14049-94-6

ZnCl2(1,10-phenanthroline)

117-39-5

quercetol

[(1,10-phenanthroline)Zn(Quercetin)Cl].3H2O

Conditions
ConditionsYield
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere;94%
117-39-5

quercetol

30048-34-1

2-(3',4'-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid

Conditions
ConditionsYield
With oxygen; tetraethylammonium tosylate In N,N-dimethyl-formamide Mechanism; electrolysis at -1.0 V, Au electrode;93%
With MES buffer; quercetinase EC 1.31.11.24 In dimethyl sulfoxide for 1h; pH=6;
With recombinant quercetinase from Aspergillus japonicus; oxygen In aq. buffer at 40 - 60℃; for 360h; pH=5; Reagent/catalyst; pH-value; Enzymatic reaction;
14491-36-2

(2,2'-bipyridyl)dichlorozinc(II)

117-39-5

quercetol

[(2,2'-bipyridine)Zn(Quercetin)Cl].3H2O

Conditions
ConditionsYield
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere;92%
14783-09-6

dichloro(1,10-phenanthroline) copper(II)

117-39-5

quercetol

[(1,10-phenanthroline)Cu(Quercetin)Cl].3H2O

Conditions
ConditionsYield
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere;92%
117-39-5

quercetol

2106-10-7

1-deoxy-1-fluoro-α-D-glucose

quercetin 7-α-O-glucoside

Conditions
ConditionsYield
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction;92%
117-39-5

quercetol

31273-65-1

2-(3,4-dihydroxy-5-sulfophenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one

Conditions
ConditionsYield
With sulfuric acid at 80℃; for 2h;90%
117-39-5

quercetol

A

116097-14-4

C15H7O16S3(3-)*3K(1+)

B

90332-36-8, 119560-46-2

quercetin-3,7,3',4'-tetrasulphate potassium

Conditions
ConditionsYield
With potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide In pyridine at 25℃; for 288h;A 89%
B n/a
2051-90-3

Dichlorodiphenylmethane

117-39-5

quercetol

357194-03-7

2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one

Conditions
ConditionsYield
In diphenylether at 175℃; for 2h;89%
In diphenylether at 175℃; for 2h;89%
In diphenylether at 175℃; for 0.5h; Inert atmosphere; regioselective reaction;86%
64-17-5

ethanol

117-39-5

quercetol

102788-22-7

2-(3,4-Dihydroxy-phenyl)-2-ethoxy-3,3,5,7-tetrahydroxy-chroman-4-one

Conditions
ConditionsYield
With oxygen; copper dichloride at 20℃; for 10h;88%
With phosphate buffer at 80℃; for 7h; Irradiation;3 mg
With phosphate buffer at 30℃; for 4h; Irradiation; enzyme solution from red clover (leaves and stems);2 mg
117-39-5

quercetol

75-03-6

ethyl iodide

82547-07-7

2-(3,4-diethoxyphenyl)-3,5,7-triethoxy-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 12h; Inert atmosphere;87%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;82%
With tetraethylammonium fluoride In N,N-dimethyl-formamide for 20h;70%
With potassium hydroxide
117-39-5

quercetol

3282-30-2

pivaloyl chloride

2-(3,4-bis(pivaloyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2,2-dimethylpropanoate)

Conditions
ConditionsYield
With pyridine for 2h; Reflux;87%
With pyridine for 16h; Ambient temperature;67%
117-39-5

quercetol

6-bromo-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

Conditions
ConditionsYield
With bromine In 1,4-dioxane at 20 - 22℃; for 2h;86.1%
Stage #1: quercetol With N-Bromosuccinimide; sodium hydroxide In methanol; water at 20℃; for 0.166667h; Inert atmosphere; Green chemistry;
Stage #2: With hydrogenchloride; sodium dithionite In methanol; water at 20℃; Inert atmosphere; Green chemistry;
400 mg
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere
2: N-Bromosuccinimide / dichloromethane / -40 °C / Inert atmosphere
3: boron trichloride / dichloromethane; hexane / 2.5 h / -20 °C / Inert atmosphere; Reflux
View Scheme
With bromine In 1,4-dioxane at 24.84℃;
117-39-5

quercetol

74-88-4

methyl iodide

1247-97-8

pentamethyl quercetin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 35℃; for 12h; Inert atmosphere;86%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h;84%
With potassium carbonate In acetone for 24h; Reflux;82%
117-39-5

quercetol

3,5,7-trihydroxy-2-(3,4-dihydroxyphenyl-2,5,6-D3)-4H-1-benzopyran-4-one-6,8-D2

Conditions
ConditionsYield
With boron trifluoride; [D3]phosphoric acid In water-d2 at 55℃; for 48h; deuteration;86%
Stage #1: quercetol With [D]-sodium hydroxide; platinum on activated charcoal; water-d2 at 130℃; for 9h; Inert atmosphere;
Stage #2: With formic acid at 130℃; for 1h; Inert atmosphere;
63%
1186389-75-2

C35H56O5

117-39-5

quercetol

1186389-71-8

C50H64O11

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 60℃; Inert atmosphere;86%
75-18-3

dimethylsulfide

117-39-5

quercetol

1245-15-4

retusin

Conditions
ConditionsYield
With potassium hydroxide In water; acetone86%
117-39-5

quercetol

147-85-3

L-proline

quercetin L-proline cocrystals(1:2)

Conditions
ConditionsYield
In ethanol at 50℃;85.5%
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Chemistry

Molecular Structure:

Molecular Formula: C15H10O7
Molecular Weight: 302.2357
IUPAC Name: 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one
Synonyms of Quercetin (CAS NO.117-39-5): 3',4',5,7-Tetrahydroxyflavan-3-ol ; 3,3',4',5,7-Pentahydroxyflavone ; 3,5,7,3',4'-Pentahydroxyflavone ; 3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-on ; 5-18-05-00494 (Beilstein Handbook Reference) ; AI3-26018 ; BRN 0317313 ; C.I. 75670 ; C.I. Natural Yellow 10 ; CCRIS 1639 ; CI 75670 ; CI Natural Yellow 10 ; EINECS 204-187-1 ; Flavin meletin ; Flavone, 3,3',4',5,7-pentahydroxy- ; HSDB 3529 ; Kvercetin ; Kvercetin [Czech] ; NCI-C60106 ; NSC 9219 ; NSC 9221 ; Quercetin content ; Sophoretin ; T-Gelb bzw. grun 1 ; UNII-9IKM0I5T1E ; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy- ; Natural Yellow 10
CAS NO: 117-39-5
Classification Code: Antioxidants ; Mutation data ; Natural Product ; Protective Agents ; Reproductive Effect ; Tumor data
Melting point: 314-317°C 
Index of Refraction: 1.823
Molar Refractivity: 73.31 cm3
Molar Volume: 167.9 cm3
Surface Tension: 114.8 dyne/cm
Density: 1.799 g/cm3
Flash Point: 248.1 °C
Enthalpy of Vaporization: 98.26 kJ/mol
Boiling Point: 642.4 °C at 760 mmHg
Vapour Pressure: 4.24E-17 mmHg at 25°C

Uses

 Quercetin (CAS NO.117-39-5) has demonstrated significant anti-inflammatory activity by inhibiting both manufacture and release of histamine and other allergic/inflammatory mediators.In addition, it exerts potent antioxidant activity and vitamin C-sparing action. It has also been claimed that quercetin reduces blood pressure in hypertensive subjects. An in-vitro study on fat cells suggested that quercetin and resveratrol may have a synergistic anti-obesity effect.
 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3gm/kg (3000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 186, 1968.
mouse LD50 intravenous 18mg/kg (18mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02589,
mouse LD50 oral 159mg/kg (159mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 77, Pg. 269, 1951.
mouse LD50 subcutaneous 97mg/kg (97mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 77, Pg. 269, 1951.
rabbit LD50 intravenous 100mg/kg (100mg/kg)   FAO Nutrition Meetings Report Series. Vol. 46A, Pg. 18, 1969.
rat LD50 oral 161mg/kg (161mg/kg)   Reviews of Environmental Contamination and Toxicology. Vol. 113, Pg. 47, 1990.

Safety Profile

Hazard Codes of Quercetin (CAS NO.117-39-5): ToxicT,IrritantXi
Risk Statements: 25-36/37/38 
R25: Toxic if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 45-36-26 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 2811
RTECS: LK8750000
HazardClass: 6.1(b)
PackingGroup: III

Specification

Drug interactions of Quercetin (CAS NO.117-39-5): It is contraindicated with some antibiotics; it may interact with fluoroquinolones (a type of medicinal antibiotic), as quercetin competitively binds to bacterial DNA gyrase. It is also a potent inhibitor of CYP3A4 and CYP2C9, which are enzymes that break down most drugs in the body.