Scutellarein
Grundinformationen
- CAS
529-53-3- Standard-SMILES
O=c1cc(-c2ccc(O)cc2)oc2cc(O)c(O)c(O)c12- InChIKey
JVXZRQGOGOXCEC-UHFFFAOYSA-N- Summenformel
- C15H10O6
- Durchschnittliche Molmasse
- 286,24 g/mol
- Monoisotopische Masse
- 286,04773804
Überblick
Scutellarein is flavone substituted with hydroxy groups at C-4', -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-).
Namen und Bezeichner
- Bevorzugter Name
- Scutellarein
- IUPAC
- 5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
- Englischer Name
- SCUTELLAREIN
- Summenformel
- C15H10O6
- Molmasse
- 286.24
Namen und Synonyme
Scutellarein529-53-36-Hydroxyapigenin5,6,7,4'-Tetrahydroxyflavone4',5,6,7-tetrahydroxyflavone5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one4',5,6,7-TetrahydroxyflavanoneP460GTI853CHEBI:9062DTXSID402009466-hydroxy-apigenin
Weitere Namen anzeigen
isocarthamidinScutillareinHigh baicaleinScutellarein-RMSCUTELLAREIN WITH HPLCScutellarein (Standard)
RefChem:931509DTXCID701234375,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneSCUTELLARTLNMFCD00017692Scutellarein (>90%)4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-6-Hydroxyapigenin;4',5,6,7-Tetrahydroxyflavone
Datenbank-Bezeichner
- CAS
529-53-3- PubChem CID
- 5281697
- DTXSID
DTXSID40200946- ChEMBL
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,4
- Polarare Oberfläche (TPSA)
- 107 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 21
- Formalladung
- 0
- Komplexität
- 439
Experimentelle und physikochemische Eigenschaften
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
LogP0.89
Endocrine DisruptorsPotential endocrine disrupting compound
Physikochemische Eigenschaften
- Schmelzpunkt
- 330 °C · 330°C
- Siedepunkt
- 642.9 · 642.9±55.0 °C(Predicted)
- Dichte
- 1.654 · 1.654±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- 1 mg/mL, · DMSO: soluble1mg/mL, clear, greenish-yellow
- pka
- 6.34 · 6.34±0.40(Predicted)
- Aggregatzustand
- powder
- Farbe
- yellow
- Biologische Quelle
- Erigeron breviscapus
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
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
- hs_code
- 29329990
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
A 2024 review notes that Scutellarein has a wide range of pharmacological properties, e.g,. anti-inflammatory, antioxidant, antiviral, neuroprotective, hypoglycemic, hypolipidemic, anticancer, and cardiovascular protective effects. The pharmacological effects involve multiple mechanisms, e.g., the scavenging of free radicals, inhibition of the activation of inflammatory signaling pathways and expression of inflammatory mediators, etc.
A 2025 review notes various possible pathways behind the mechanism(s) of action, and interest due to its wide pharmacological effects, e.g., anticancer, anti-inflammation, antioxidant, antiobesity, and vasorelaxant. The review also notes positive treatment results related to neurons, liver, heart, lung, kidney, bone, skin protective experiments, and human sperm function enhancement.
Metabolism/MetabolitesScutellarein has known human metabolites that include Scutellarein 7-O-glucuronide.
Anwendungen
BeschreibungScutellarein is a flavone that has been isolated from S. baicalensis and has antioxidant, enzyme inhibitory, anti-inflammatory, and antiproliferative biological activities. It has antioxidant activity in a total reactive antioxidant potential (TRAP) assay when used at a concentration of 1 μg/ml. Scutellarein inhibits sucrose hydrolysis by rat intestinal α-glucosidase and ATPase activity of the severe acute respiratory syndrome (SARS) coronavirus helicase nsP13 (IC50s = 12 and 0.86 μM, respectively). It decreases nitric oxide (NO) release and mRNA expression of inducible NO synthase (iNOS) and TNF-α induced by LPS in RAW 264.7 macrophages when used at a concentration of 50 μM. In vivo, scutellarein (0.5 μg/g) decreases tumor weight and volume in an HT-1080 human fibrosarcoma mouse xenograft model.
VerwendenScutellarein is a flavonoid that can be found in Scutellaria lateriflora. Scutellarein is a hydrolysis product of Scutellarein (S201900), its glucuronide conjugated analogue.
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