Basic information
- CAS
529-53-3- Standard SMILES
O=c1cc(-c2ccc(O)cc2)oc2cc(O)c(O)c(O)c12- InChIKey
JVXZRQGOGOXCEC-UHFFFAOYSA-N- Molecular formula
- C15H10O6
- Average molar mass
- 286.24 g/mol
- Monoisotopic mass
- 286.04773804
Overview
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-).
Names & identifiers
- Preferred name
- Scutellarein
- IUPAC
- 5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
- English name
- SCUTELLAREIN
- Molecular formula
- C15H10O6
- Molecular weight
- 286.24
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
529-53-3- PubChem CID
- 5281697
- DTXSID
DTXSID40200946- ChEMBL
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 439
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
LogP0.89
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 330 °C · 330°C
- Boiling point
- 642.9 · 642.9±55.0 °C(Predicted)
- Density
- 1.654 · 1.654±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 1 mg/mL, · DMSO: soluble1mg/mL, clear, greenish-yellow
- pka
- 6.34 · 6.34±0.40(Predicted)
- form
- powder
- color
- yellow
- biological source
- Erigeron breviscapus
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
Safety & regulation
Safety data
- wgk
- 3
- hs_code
- 29329990
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
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.
Applications
DescriptionScutellarein 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.
UsesScutellarein is a flavonoid that can be found in Scutellaria lateriflora. Scutellarein is a hydrolysis product of Scutellarein (S201900), its glucuronide conjugated analogue.
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
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