Structure via PubChem · Public domain (PubChem)
flavonol
Sign in to saveAlso known as 3-Hydroxyflavone, 3-hydroxy-2-phenyl-4H-1-benzopyran-4-one, flavon-3-ol, 3-hydroxy-2-phenylchromone
3-Hydroxyflavone is a chemical compound. It is the backbone of all flavonols, a type of flavonoid. It is a synthetic compound, which is not found naturally in plants. It serves as a model molecule as it possesses an excited-state intramolecular proton transfer (ESIPT) effect to serve as a fluorescent probe to study membranes for example or intermembrane proteins. The green tautomer emission (λmax ≈ 524 nm) and blue-violet normal emission (λmax ≈ 400 nm) originate from two different ground state populations of 3HF molecules. The phenomenon also exists in natural flavonols. Although 3-
Chemical data
- Formula
- C15H10O3
- Molecular weight
- 238.24 g/mol
- IUPAC name
- 3-hydroxy-2-phenylchromen-4-one
- SMILES
- C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
- InChIKey
- HVQAJTFOCKOKIN-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 46.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- flavone
- Mass
- 238.063
Show 5 more facts
- found in taxon
- Eucalyptus camaldulensis
- chemical formula
- C₁₅H₁₀O₃
- canonical SMILES
- C1=CC=C(C=C1)C2=C(C(=O)C3=CC=CC=C3O2)O
- Commons category
- Flavonol
- melting point
- 170.0
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
3-Hydroxyflavone is a chemical compound. It is the backbone of all flavonols, a type of flavonoid. It is a synthetic compound, which is not found naturally in plants. It serves as a model molecule as it possesses an excited-state intramolecular proton transfer (ESIPT) effect to serve as a fluorescent probe to study membranes for example or intermembrane proteins. The green tautomer emission (λmax ≈ 524 nm) and blue-violet normal emission (λmax ≈ 400 nm) originate from two different ground state populations of 3HF molecules. The phenomenon also exists in natural flavonols. Although 3-hydroxyflavone is almost insoluble in water, its aqueous solubility (hence bio-availability) can be increased by encapsulation in cyclodextrin cavities.
==Synthesis== The Algar-Flynn-Oyamada reaction is a chemical reaction whereby a chalcone undergoes an oxidative cyclization to form a flavonol. 400px|none|Algar-Flynn-Oyamada reaction
Excerpted from Wikipedia’s “flavonol” article, available under the CC BY-SA 4.0 licence.