Baicalein
Grundinformationen
- CAS
27462-75-5- Standard-SMILES
O=c1cc(-c2ccccc2)oc2cc(O)c(O)c(O)c12- InChIKey
FXNFHKRTJBSTCS-UHFFFAOYSA-N- Summenformel
- C15H10O5
- Durchschnittliche Molmasse
- 270,24 g/mol
Überblick
Baicalein is a trihydroxyflavone with the hydroxy groups at positions C-5, -6 and -7. It has a role as an EC 4.1.1.17 (ornithine decarboxylase) inhibitor, an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, a ferroptosis inhibitor, a geroprotector, an antioxidant, an antibacterial agent, an antineoplastic agent, an antifungal agent, an angiogenesis inhibitor, a radical scavenger, a hormone antagonist, a prostaglandin antagonist, an EC 1.13.11.31 (arachidonate 12-lipoxygenase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an anti-inflammatory agent, an apoptosis inducer, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor and a plant metabolite. It is a conjugate acid of a baicalein(1-).
Namen und Bezeichner
- Bevorzugter Name
- Baicalein
- IUPAC
- 5,6,7-trihydroxy-2-phenylchromen-4-one
- Englischer Name
- BAICALEIN
- Summenformel
- C21H18O11
- Molmasse
- 270.24
Namen und Synonyme
baicalein491-67-85,6,7-TrihydroxyflavoneNoroxylin5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one5,6,7-trihydroxy-2-phenylchromen-4-one5,6,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-oneNSC-661431CHEBI:2979DTXSID202238949QAH60606RefChem:5579
Weitere Namen anzeigen
DTXCID802389637-183-7MFCD00017459Baicalein, 98%5,6,7-trihydroxy-2-phenyl-chromen-4-one4H-1-Benzopyran-4-one, 5,6,7-trihydroxy-2-phenyl-SpecPlus_000758Spectrum5_001418
Datenbank-Bezeichner
- CAS
27462-75-5- ChEMBL
CHEMBL8260- ChEBI
CHEBI:2979- UNII
- 49QAH60606
- EC Number
- 637-183-7
- Nikkaji
- J22.048E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,7
- Polarare Oberfläche (TPSA)
- 87 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 20
- Formalladung
- 0
- Komplexität
- 412
Experimentelle und physikochemische Eigenschaften
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
153.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
182.55 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
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
H315 (95.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationBaicalein: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (95.8%)
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Compounds that inhibit the action of prostaglandins.
Absorption, Distribution and Excretion
A 2025 systematic review notes that while Baicalin has poor oral bioavailability due to its low water solubility and limited membrane permeability, Baicalein exhibits superior lipophilicity and permeability. Baicalin is hydrolyzed to Baicalein by gut microbiota and enzymes. UDP-glucuronosyltransferases in enterocytes in the intestines and in the liver can convert Baicalein back to Baicalin. Thus, conversion of Bacalin to Baicalein facilitates systemic uptake while re-glucuronidation of Bacalein to Bacalin potentially prolongs the therapeutic effects.
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