3-Hydroxyflavone

3-Hydroxyflavone
Names
IUPAC name
3-Hydroxyflavone
Systematic IUPAC name
3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one
Other names
Flavon-3-ol
3-HF
3-Hydroxy-2-phenylchromone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.562
KEGG
UNII
  • InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H Y
    Key: HVQAJTFOCKOKIN-UHFFFAOYSA-N Y
  • InChI=1/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
    Key: HVQAJTFOCKOKIN-UHFFFAOYAX
  • O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3
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).
Y verify (what is YN ?)
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 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.

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