3-Hydroxyflavone

3-Hydroxyflavone

Names
IUPAC name 3-hydroxy-2-phenylchromen-4-one
Other names 3-Hydroxyflavone Flavon-3-ol 3-HF 3-Hydroxy-2-phenylchromone
Identifiers
CAS Number	577-85-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:5078 Y
ChEMBL	ChEMBL294009 Y
ChemSpider	10871 Y
ECHA InfoCard	100.008.562
KEGG	C01495 Y
PubChem	11349
InChI 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
SMILES O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3
Properties
Chemical formula	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^[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

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

References