3-Hydroxyflavone

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3-Hydroxyflavone
Skeletal formula of 3-hydroxyflavone
Ball-and-stick model of the 3-hydroxyflavone molecule
Names
IUPAC name
3-hydroxy-2-phenylchromen-4-one
Other names
3-Hydroxyflavone
Flavon-3-ol
3-HF
3-Hydroxy-2-phenylchromone
Identifiers
577-85-5 YesY
ChEBI CHEBI:5078 YesY
ChEMBL ChEMBL294009 YesY
ChemSpider 10871 YesY
Jmol-3D images Image
KEGG C01495 YesY
PubChem 11349
Properties
C15H10O3
Molar mass 238.23 g/mol
Density 1.367 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox 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[1] to serve as a fluorescent probe to study membranes for example[2] or intermembrane proteins.[3] 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.[4] 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 cavitiies [5]

Synthesis[edit]

The Algar-Flynn-Oyamada reaction is a chemical reaction whereby a chalcone undergoes an oxidative cyclization to form a flavonol.

Algar-Flynn-Oyamada reaction








References[edit]