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Quercetin

3-[(O-6-Deoxy-α-L-mannopyranosyl-(1→2)-O-6-deoxy-α-L-mannopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one

HCID 10283929
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Grundinformationen

CAS
117-39-5
Standard-SMILES
C[C@@H]1O[C@@H](O[C@H]2[C@H](OC[C@H]3O[C@@H](Oc4c(-c5ccc(O)c(O)c5)oc5cc(O)cc(O)c5c4=O)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H](C)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey
ZKLZXRYXKRWGQP-RHZMNZKUSA-N
Summenformel
C33H40O20
Durchschnittliche Molmasse
756,663 g/mol
Monoisotopische Masse
756,21129368

Namen und Bezeichner

Bevorzugter Name
3-[(O-6-Deoxy-α-L-mannopyranosyl-(1→2)-O-6-deoxy-α-L-mannopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Lokaler Name
Quercetin
Englischer Name
Quercetin
Summenformel
C15H10O7
Molmasse
302.24

Namen und Synonyme

2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-oneQUERCETINEQuercetin anhydrousnaturalQUERCITINMELETINQUERCETOLQUERTINEPentahydroxyflavoneSOPHORETIN

Datenbank-Bezeichner

CAS
117-39-5、32453-37-5
PubChem CID
10283929
DTXSID
DTXSID901099829

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
316.5 °C · 316.5 °C
Siedepunkt
363.28 °C · 363.28°C (rough estimate)
Dichte
1.3616 · 1.3616 (rough estimate)
Brechungsindex
1.479 · 1.4790 (estimate)
storage temp.
room temp
Löslichkeit
2 O; · insoluble in H2O; ≥15.1 mg/mL in DMSO; ≥3.28 mg/mL in EtOH
Aggregatzustand
solid
pka
6.31 · 6.31±0.40(Predicted)
Farbe
Yellowish
Biologische Quelle
synthetic (organic)
Wasserlöslichkeit
0.1 g/100 · <0.1 g/100 mL at 21 ºC
Merck
13 · 13,8122
BRN
317313 · 317313
Kosmetik-Inhaltsstoffe Funktionen
ANTIOXIDANTSKIN CONDITIONING - MISCELLANEOUS
InChI
1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
InChIKey
REFJWTPEDVJJIY-UHFFFAOYSA-N
SMILES
OC1=CC(O)=C2C(OC(C3=CC=C(O)C(O)=C3)=C(O)C2=O)=C1
LogP
1.989 · 1.989 (est)
CAS Datenbank
117 · 117-39-5(CAS DataBase Reference)
EPA chemische Informationen
Quercetin (117-39-5)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
2811
hs_code
29329990
RTECS-Nr.
LK8750000
risk_code
25-36/37/38
Toxizität
LD50 oral in rat: 161mg/kg
hazard_code
T,Xi
safety_code
45-36-26
hazard_class
6.1(b)
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
117-39-5(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 Oral

Chemie und Industrie

Anwendungen · 3 Einträge

BeschreibungThe name of quercetin has been used since 1857, which is derived from quercetum (oak forest) after Quercus. Quercetin is widely found in flowers, leaves, and fruits of various plants. Vegetables (such as onions, ginger, celery, etc.), fruits (such as apples, strawberries, etc.), beverages (such as tea, coffee, red wine, fruit juice, etc.), and more than 100 kinds of Chinese herbal medicines (such as Threevein Aster, mountain white chrysanthemum, Huai rice, Apocynum, Ginkgo biloba, etc.) contain this ingredient. Threevein Aster is a Chinese herbal medicine and used in Jiangxi province, China, for more than 30 years. Its plant name is three veins Mala, Compositae. It is rich in drug sources, which can be found in Southern provinces of China. Clinical practice proved that it has significant anti-inflammatory and expectorant effects, and it is a good prescription for the treatment of elderly chronic bronchitis.

HistoryIn 1936, Szent-Gyorgyi firstly reported the separation and identification of biological activity of quercetin. Usually quercetin is presented in the form of glycosides such as lutin, quercitrin, and mycoside, which can be hydrolyzed to get the quercetin. Quercetin has a polyphenol hydroxyl structure, which is of weak lipophilicity and poor hydrophilicity, resulting in its low bioavailability and limiting its clinical application. The synthesis of phenolic derivatives improves its bioavailability, which are lipid-soluble quercetin derivatives such as 3-O-methylquercetin, hydrophilic quercetin derivatives such as 3′-ON-carboxymethylformamide quercetin, and quercetin glycosides. Threevein Aster, having quercetin as one of the main active ingredients, has been used for the domestic clinical treatment for chronic bronchitis in China since 1971.

VerwendenQuercetin has been used as an antioxidant which reversed the immunosuppressive effects of high glucose and hyperglycemic sera in type 2 diabetic patients.It has been used as a detoxifying phytochemical in Apis mellifera.It has been used as a positive control in DPPH (2,2- diphenyl-1-picryhydrazyl) radical scavenging assay. It has also been used for the preparation of calibration curve to determine total flavonoid content.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Anise oil

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ISOQUERCETIN(P)
Rutosid
2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on
Quercitrin
3,3',4',5,7-Pentahydroxyflavanone

Nachgelagerte Produkte

2-(3,4-Dimethoxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-one3,3'-di-O-methylquercetin2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyronpachypodol3,4'-Dimethoxy-3',5,7-trihydroxyflavone3,7-Dimethoxy-3',4',5-trihydroxyflavone4',7-Dimethoxy-3,3',5-trihydroxyflavoneAYANIN