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
3D model (Jmol)	Interactive image
ChEBI	CHEBI:5078
ChEMBL	ChEMBL294009
ChemSpider	10871
ECHA InfoCard	100.008.562
KEGG	C01495
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 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).
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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

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

References

1. All-optical switchings of 3-hydroxyflavone in different solvents. Wu Feng, Lin Lie, Li Xiang-Ping, Yu Ya-Xin, Zhang Gui-Lan and Chen Wen-Ju, Chinese Phys. B 17 1461-1466.
2. Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes. Jayanti Guharay , Rupali Chaudhuri , Abhijit Chakrabarti and Pradeep K. Sengupta, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Volume 53, Issue 3, March 1997, Pages 457-462
3. Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects. Sudip Chaudhuri, Anwesha Banerjee, Kaushik Basu, Bidisha Sengupta, and Pradeep K. Sengupta, International Journal of Biological Macromolecules, Volume 41, Issue 1, 1 June 2007, Pages 42-48
4. Effect of reverse micelles on the intramolecular excited state proton transfer (ESPT) and dual luminescence behaviour of 3-hydroxyflavone. Munna Sarkar, Jayanti Guha Ray and Pradeep K. Sengupta, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Volume 52, Issue 2, February 1996, Pages 275-278
5. Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies. Biswapathik Pahari, Sandipan Chakraborty, Pradeep K. Sengupta.Journal of Molecular Structure, Volume 1006, Issues 1–3, 14 December 2011, Pages 483–488