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
CAS Number	577-85-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5078 ;
ChEMBL	ChEMBL294009 ;
ChemSpider	10871 ;
ECHA InfoCard	100.008.562
KEGG	C01495 ;
PubChem CID	11349;
UNII	ZTG9LSS5QH ;
CompTox Dashboard (EPA)	DTXSID4060365 ;
	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 Key: HVQAJTFOCKOKIN-UHFFFAOYSA-N ; 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). verify (what is ?) 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 (λ_max ≈ 524 nm) and blue-violet normal emission (λ_max ≈ 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 cavities.^[5]

Synthesis

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

References

[1]

[2]

[3]

[4]

[5]

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
CAS Number	577-85-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5078^Y
ChEMBL	ChEMBL294009^Y
ChemSpider	10871^Y
ECHA InfoCard	100.008.562
KEGG	C01495^Y
PubChem CID	11349
UNII	ZTG9LSS5QH^Y
CompTox Dashboard (EPA)	DTXSID4060365
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