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3-Hydroxyflavone

3-HF 3-Hydroxy-2-phenylchromone 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.

Synthesis

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

References

[http://www.iop.org/EJ/abstract/1674-1056/17/4/052 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.]
(1997). "Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.
(2007). "Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects". International Journal of Biological Macromolecules.
(1996). "Effect of reverse micelles on the intramolecular excited state proton transfer (ESPT) and dual luminescence behaviour of 3-hydroxyflavone". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.
(2011). "Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies". Journal of Molecular Structure.

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flavonols

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