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 (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).
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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 (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.

Algar-Flynn-Oyamada reaction

References

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.
Guharay, Jayanti; Chaudhuri, Rupali; Chakrabarti, Abhijit; Sengupta, Pradeep K. (1997). "Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 53 (3): 457–462. doi:10.1016/S1386-1425(96)01825-2.
Chaudhuri, Sudip; Banerjee, Anwesha; Basu, Kaushik; Sengupta, Bidisa; Sengupta, Pradeep K. (2007). "Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects". International Journal of Biological Macromolecules. 41: 42–48. doi:10.1016/j.ijbiomac.2006.12.003. PMID 17239435.
Sarkar, Munna; Guha Ray, Jayanti; Sengupta, Pradeep K. (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. 52 (2): 275–278. doi:10.1016/0584-8539(95)01622-8.
Pahari, Biswapathik; Chakraborty, Sandipan; Sengupta, Pradeep K. (2011). "Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies". Journal of Molecular Structure. 1006 (1–3): 483–488. doi:10.1016/j.molstruc.2011.09.055.

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[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] Guharay, Jayanti; Chaudhuri, Rupali; Chakrabarti, Abhijit; Sengupta, Pradeep K. (1997). "Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 53 (3): 457–462. doi:10.1016/S1386-1425(96)01825-2.

[3] Chaudhuri, Sudip; Banerjee, Anwesha; Basu, Kaushik; Sengupta, Bidisa; Sengupta, Pradeep K. (2007). "Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects". International Journal of Biological Macromolecules. 41: 42–48. doi:10.1016/j.ijbiomac.2006.12.003. PMID 17239435.

[4] Sarkar, Munna; Guha Ray, Jayanti; Sengupta, Pradeep K. (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. 52 (2): 275–278. doi:10.1016/0584-8539(95)01622-8.

[5] Pahari, Biswapathik; Chakraborty, Sandipan; Sengupta, Pradeep K. (2011). "Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies". Journal of Molecular Structure. 1006 (1–3): 483–488. doi:10.1016/j.molstruc.2011.09.055.