Conditions | Yield |
---|---|
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% |
hydrogenchloride
quercetin triphenylantimony complex
A
quercetol
B
triphenylantimony dichloride
Conditions | Yield |
---|---|
heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene; | A 75% B 88% |
6,8-dibromoquercetin
quercetol
Conditions | Yield |
---|---|
With sodium sulfite In water at 60℃; for 18h; Green chemistry; | 87% |
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane for 6h; Heating; | 83% |
With trimethylsilyl iodide In methanol at 35℃; for 96h; Inert atmosphere; |
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 1h; | A n/a B 68% |
With grape snail enzymes | |
With rhamnodiastase |
Conditions | Yield |
---|---|
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% |
quercetin 7-O-β-D-glucopyranoside
quercetol
Conditions | Yield |
---|---|
Acid hydrolysis; | 68% |
With sulfuric acid for 1h; Heating; |
quercetin 7-O-β-D-glucopyranoside
A
D-glucose
B
quercetol
Conditions | Yield |
---|---|
With water Acidic conditions; | A n/a B 65% |
With water Acidic conditions; |
Conditions | Yield |
---|---|
With sulfuric acid | A 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; |
Conditions | Yield |
---|---|
With water Acidic conditions; | A n/a B 64% |
Acidic conditions; | |
Acidic aq. solution; |
guaijaverin
A
L-(+)-arabinose
B
quercetol
Conditions | Yield |
---|---|
With sulfuric acid for 3h; | A n/a B 63.5% |
Conditions | Yield |
---|---|
Acidic conditions; | 63.3% |
With oxonium | |
With hydrogenchloride; ethanol for 4h; Heating; |
Conditions | Yield |
---|---|
Acidic conditions; | 63.3% |
Acid hydrolysis; | |
With hydrogenchloride In water for 0.5h; Reflux; |
rutin
A
6-O-α-L-rhamnopyranosyl-β-D-glucopyranose
B
quercetol
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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 |
3,3',4',5,7-pentahydroxy flavanone
quercetol
Conditions | Yield |
---|---|
With potassium pyrosulfite In ethanol at 100℃; | 50% |
With pyridine; air for 20h; Heating; |
Conditions | Yield |
---|---|
With sulfuric acid; water | A n/a B n/a C 47% |
With sulfuric acid | |
With hydrogenchloride; water In methanol at 100℃; for 2h; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 72h; | 28% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With water; hydrogen iodide; acetic anhydride at 150℃; |
Conditions | Yield |
---|---|
With water; hydrogen iodide at 150℃; |
2-benzo[1,3]dioxol-5-yl-3-hydroxy-5,7-dimethoxy-chromen-4-one
quercetol
Conditions | Yield |
---|---|
With aluminium trichloride; chlorobenzene at 130℃; Erwaermen des Reaktionsgemisches mit wss. HCl; |
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; |
Conditions | Yield |
---|---|
Product distribution; acid hydrolysis; |
quercitrin
A
D-rhamnose
B
quercetol
Conditions | Yield |
---|---|
hesperidinase |
Conditions | Yield |
---|---|
With hydrogenchloride | |
With sulfuric acid |
quercetin-3-arabinoside
A
L-(+)-arabinose
B
quercetol
Conditions | Yield |
---|---|
With hydrogenchloride boiling water bath; |
manghaslin
A
D-Glucose
B
L-rhamnose
C
quercetol
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Product distribution; Heating; hydrolysis for structure determination;sugar products were identified as their trimethylsilyl derivatives by GC-MS; |
3,3',4',5,7-pentahydroxyflavone 3-O-arabogluocopyranoside
A
D-arabinofuranose
B
quercetol
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; |
quercetol
acetic anhydride
3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one
Conditions | Yield |
---|---|
With pyridine at 130 - 140℃; | 100% |
With pyridine at 140 - 145℃; for 4h; | 97.5% |
With pyridine at 70℃; for 6h; | 95% |
quercetol
Conditions | Yield |
---|---|
With hydrogenchloride; selenium(IV) oxide In ethanol; water at 60℃; for 12h; Inert atmosphere; | 99.2% |
Conditions | Yield |
---|---|
With magnesium In neat (no solvent) at 25℃; for 3.5h; Temperature; | 98% |
Conditions | Yield |
---|---|
With 1% disodium hydrogen phosphate-sodium citrate; 35-40% glucosyltransferase at 40 - 45℃; Enzymatic reaction; | 97.2% |
quercetol
benzoyl chloride
2-(3,4-bis(benzoyloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tribenzoate
Conditions | Yield |
---|---|
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 |
quercetol
2-Methylpropionic anhydride
2-(3,4-bis(isobutyryloxy)phenyl)-4-oxo-4H-chromene-3,5,7-triyl tris(2-methylpropanoate)
Conditions | Yield |
---|---|
With pyridine for 2h; Reflux; | 97% |
In pyridine Ambient temperature; | 0.43 g |
quercetol
tert-butyldimethylsilyl chloride
3,3',4',5,7-penta-O-tert-butyldimethylsilylquercetin
Conditions | Yield |
---|---|
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; |
quercetol
benzyl bromide
2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one
Conditions | Yield |
---|---|
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% |
quercetol
benzyl chloride
2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)chromen-4-one
Conditions | Yield |
---|---|
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% |
quercetol
sodium acetate
acetic anhydride
3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one
Conditions | Yield |
---|---|
Reflux; Inert atmosphere; | 95% |
ZnCl2(1,10-phenanthroline)
quercetol
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere; | 94% |
quercetol
2-(3',4'-dihydroxybenzoyloxy)-4,6-dihydroxybenzoic acid
Conditions | Yield |
---|---|
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; |
(2,2'-bipyridyl)dichlorozinc(II)
quercetol
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere; | 92% |
dichloro(1,10-phenanthroline) copper(II)
quercetol
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 20℃; for 0.166667h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction; | 92% |
quercetol
2-(3,4-dihydroxy-5-sulfophenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one
Conditions | Yield |
---|---|
With sulfuric acid at 80℃; for 2h; | 90% |
quercetol
A
C15H7O16S3(3-)*3K(1+)
B
quercetin-3,7,3',4'-tetrasulphate potassium
Conditions | Yield |
---|---|
With potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; dicyclohexyl-carbodiimide In pyridine at 25℃; for 288h; | A 89% B n/a |
Dichlorodiphenylmethane
quercetol
2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one
Conditions | Yield |
---|---|
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% |
ethanol
quercetol
2-(3,4-Dihydroxy-phenyl)-2-ethoxy-3,3,5,7-tetrahydroxy-chroman-4-one
Conditions | Yield |
---|---|
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 |
quercetol
ethyl iodide
2-(3,4-diethoxyphenyl)-3,5,7-triethoxy-4H-chromen-4-one
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With pyridine for 2h; Reflux; | 87% |
With pyridine for 16h; Ambient temperature; | 67% |
quercetol
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
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% |
quercetol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 60℃; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetone | 86% |
Conditions | Yield |
---|---|
In ethanol at 50℃; | 85.5% |
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
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.
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. |
Hazard Codes of Quercetin (CAS NO.117-39-5): T,Xi
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
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.
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