(S)-7-(β-D-Glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-on
Prunin
Grundinformationen
- CAS
529-55-5- Standard-SMILES
O=C1C[C@@H](c2ccc(O)cc2)Oc2cc(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c21- InChIKey
DLIKSSGEMUFQOK-SFTVRKLSSA-N- Summenformel
- C21H22O10
- Durchschnittliche Molmasse
- 434,4 g/mol
- Monoisotopische Masse
- 434,12129689
Überblick
Naringenin 7-O-beta-D-glucoside is a flavanone 7-O-beta-D-glucoside that is (S)-naringenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a metabolite, an antibacterial agent, a hypoglycemic agent and an antilipemic drug. It is a flavanone 7-O-beta-D-glucoside, a member of 4'-hydroxyflavanones, a (2S)-flavan-4-one, a dihydroxyflavanone and a monosaccharide derivative. It is functionally related to a (S)-naringenin.
Namen und Bezeichner
- Bevorzugter Name
- Prunin
- IUPAC
- (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
- Lokaler Name
- (S)-7-(β-D-Glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-on
- Englischer Name
- Prunin
- Summenformel
- C21H22O10
- Molmasse
- 434.4
Namen und Synonyme
Prunin529-55-5Naringenin 7-O-beta-D-glucosidePRUNIN PROTEIN, PRUNUSLSB8HDX4E5Pru du 6 protein, PrunusCHEBI:28327DTXSID40967365(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl beta-D-glucopyranosideNSC-135064(2S)-5-HYDROXY-2-(4-HYDROXYPHENYL)-7-((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXY-2,3-DIHYDROCHROMEN-4-ONE(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Weitere Namen anzeigen
NARINGENIN-7-O-GLUCOSIDENaringenin 7-O-β-D-glucopyranosideNARINGENIN-7-GLUCOSIDENaringenin-7-O-β-D-glucosidePrunnin,Prunin-7-(((2S,3R,4S,5S,6R)Prunin, 10 mM in DMSONARINGENIN-7-GLUCOSIDE hplc(-)-Naringenin 7-b-D-glucoside
RefChem:870060DTXCID301527428(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one208-464-8SCHEMBL318229(S)-7-(beta-D-Glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneAC-35062CS-0017098
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 166 Ų
- H-Brücken-Donoren
- 6
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 623
Experimentelle und physikochemische Eigenschaften
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Physikochemische Eigenschaften
- Schmelzpunkt
- 222 · 222-224°C
- Siedepunkt
- 802.4 · 802.4±65.0 °C(Predicted)
- Dichte
- 1.597 · 1.597±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 20 · DMSO:20.0(Max Conc. mg/mL);46.04(Max Conc. mM)DMF:30.0(Max Conc. mg/mL);69.06(Max Conc. mM)DMF:PBS (pH 7.2) (1:2):0.3(Max Conc. mg/mL);0.69(Max Conc. mM)
- Aggregatzustand
- A solid
- pka
- 7.18 · 7.18±0.40(Predicted)
- Farbe
- White to off-white
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- Kosmetik-Inhaltsstoffe Funktionen
- ANTIOXIDANTSKIN PROTECTINGSKIN CONDITIONING - HUMECTANT
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
Warning
H400 (95%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAquatic Acute 1 (95%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- risk_code
- 22-50
- hazard_code
- N
- safety_code
- 22-45-61
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
Chemie und Industrie
Anwendungen
VerwendenPrunin is a naturally occurring flavonoid which displays tyrosine phosphatase 1B inhibition. Also stimulates glucose uptake in insulin-resistant HepG2 cells.
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