Quercitrin
Grundinformationen
- CAS
522-12-3- Standard-SMILES
C[C@@H]1O[C@@H](Oc2c(-c3ccc(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
OXGUCUVFOIWWQJ-HQBVPOQASA-N- Summenformel
- C21H20O11
- Durchschnittliche Molmasse
- 448,4 g/mol
- Monoisotopische Masse
- 448,10056145
Überblick
Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor and a plant metabolite. It is an alpha-L-rhamnoside, a tetrahydroxyflavone, a monosaccharide derivative and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate.
Namen und Bezeichner
- Bevorzugter Name
- Quercitrin
- IUPAC
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
- Lokaler Name
- Quercitrin
- Englischer Name
- Quercitrin
- Summenformel
- C21H20O11
- Molmasse
- 448.38
Namen und Synonyme
quercitrin522-12-3QuercitrosideQuercetin 3-rhamnosideQuercetrinQuercimelinThujinQuercetin-3-L-rhamnosideQuercetin 3-L-rhamnosideRhamnoside, quercetin-3Usaf cf-2QUERCETIN 3-RHAMNOPYRANOSIDE
Weitere Namen anzeigen
FLAVINQUERCETIN-3-O-RHAMNOSIDEQUERCETIN-3-RHAMNOSIDEquercitrin hydrateci75720usafcf-2c.i.75720
C.I. 75720NCI-C60102Quercetin 3-O-alpha-rhamnopyranoside3,3',4',5,7-Pentahydroxyflavone-3-L-rhamnosideCHEBI:17558DTXSID502002302Y8906LC5PQuercetin, 3-(6-deoxy-alpha-L-mannopyranoside)
Datenbank-Bezeichner
- CAS
522-12-3- PubChem CID
- 5280459
- DTXSID
DTXSID50200230- ChEMBL
CHEMBL2262641、CHEMBL82242- ChEBI
CHEBI:17558- UNII
- 2Y8906LC5P
- EC Number
- 208-322-5
- Nikkaji
- J1.578D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 186 Ų
- H-Brücken-Donoren
- 7
- H-Brücken-Akzeptoren
- 11
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 32
- Formalladung
- 0
- Komplexität
- 741
Experimentelle und physikochemische Eigenschaften
Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LogP1.78
Color/FormYELLOW CRYSTALS FROM DIL METHANOL OR ETHANOL
Solubility
PRACTICALLY INSOL IN COLD WATER, ETHER; SOL IN ALCOHOL; MODERATELY SOL IN HOT WATER; SOL IN AQ ALKALINE SOLN
0.064 mg/mL at 16 °C
Melting Point
176-179 °C; FROM WATER, MP 167 °C
250 - 252 °C
Physical Description
Yellow solid; [Merck Index]
Solid
Stability/Shelf LifeIN AQ ALKALINE SOLN INTENSE YELLOW COLOR WHICH IS OXIDIZED BY AIR TO BROWN
Collision Cross Section
206.35 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
205.9 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 174 · 174-183°C
- Siedepunkt
- 477.14 °C · 477.14°C (rough estimate)
- Dichte
- 1.3943 · 1.3943 (rough estimate)
- Brechungsindex
- 1.5376 · 1.5376 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Sonicated)
- Aggregatzustand
- Solid
- pka
- 6.17 · 6.17±0.40(Predicted)
- Farbe
- Light Yellow to Dark Yellow
- Merck
- 8125 · 8125
- BRN
- 68135 · 68135
- Stabilität
- Hygroscopic
- Major Application
- food and beverages
- InChIKey
- OXGUCUVFOIWWQJ-HQBVPOQASA-N
- SMILES
- C[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O
- LogP
- 0.579 · 0.579 (est)
- CAS Datenbank
- 522 · 522-12-3(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.
Not Classified
Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazards SummaryIntraperitoneal LD50 (mouse) = 200 mg/kg; [RTECS] May cause irritation; [MSDSonline]
Hazard Classes and CategoriesNot Classified
Toxikologische Informationen
Non-Human Toxicity Excerpts
QUERCITRIN WAS ASSAYED FOR MUTAGENICITY IN SALMONELLA/(RAT LIVER) MICROSOMAL ACTIVATION SYSTEM & WAS MUTAGENIC IN HISTIDINE REVERSION SYSTEM WITH FRAMESHIFT STRAIN TA98.
INFLAMMATORY DISEASE WAS SIMULATED BY INJECTION OF PLASMA KININS, KALLIDIN & BRADYKININ, WHICH INCR CAPILLARY PERMEABILITY & LYMPH FLOW (EXCEPT IN LIVER & KIDNEY). QUERCITRIN INCR LYMPH SECRETION & ANTAGONIZED KALLIDIN EFFECT @ 50-250 MG/KG.
GROWTH INHIBITION OF HELIOTHIS ZEA LARVAE BY 42 FLAVONOIDS ADDED TO DIET STUDIED. VICINAL HYDROXYLATION NECESSARY FOR ACTIVITY, BUT WAS NOT SUFFICIENT FOR ALL COMPD SINCE SOME WERE INACTIVE. SOME COMPD WITH DIFFERENT POLARITIES EQUALLY ACTIVE (QUERCITRIN & QUERCETIN).
QUERCITRIN WAS NOT MUTAGENIC IN SALMONELLA/MAMMALIAN MICROSOME TEST.
Sicherheitsdaten
- F
- 10-23
- wgk
- 3
- hs_code
- 29389090
- RTECS-Nr.
- UZ5950000
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 522-12-3(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
YIELDS QUERCETIN IN ASPERGILLUS; WESTLAKE DWS, CAN J MICROBIOL 9: 211 (1963); YIELDS QUERCITRIN QUINONE PROBABLY IN POLYPORUS; PICKARD MA & WESTLAKE DWS, CAN J BIOCHEM 48: 1351 (1970). /FROM TABLE/
Quercitrin has known human metabolites that include L-Rhamnose, Quercetin, and alpha-L-Rhamnose.
Cellular LocationsCytoplasm
Verwendung und Herstellung
Uses
From the tree Aesculus hippocastanum L., Hippocastanaceae; Has been used to dye textiles; Main constituent of flavine yellow shade; [Merck Index] Formerly used as a dye for wool; [HSDB]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
DYE FORMERLY USED ON WOOL MORDANTED WITH TIN AND ALUM
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of Manufacturing
EXTRACTION (AS MIXTURE WITH QUERCETIN) FROM BARK OF QUECUS TINCTORIA WITH HIGH PRESSURE STEAM
FROM AESCULUS HIPPOCASTANUM L, HIPPOCASTANACEAE: HORHAMMER ET AL, ARCH PHARM 292, 113 (1959).
General Manufacturing InformationHAS BEEN USED AS TEXTILE DYE. FLAVINE YELLOW SHADE IS PREPARED BY EXTRACTING QUERCITRON BARK WITH HIGH PRESSURE STEAM AND CONSISTS MAINLY OF QUERCITRIN; TISDALE, CAN TEXTILE J 57, 44 (1941).
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Ergänzende Hinweise
DefinitionChEBI: Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a monosaccharide derivative, a tetrahydroxyflavone, an alpha-L-rhamnoside and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate.
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