3-Hydroxyflavone

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 cavities.[5]

3-Hydroxyflavone
Skeletal formula of 3-hydroxyflavone
Ball-and-stick model of the 3-hydroxyflavone molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.562
KEGG
UNII
  • 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 checkY
    Key: HVQAJTFOCKOKIN-UHFFFAOYSA-N checkY
  • 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
  • O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3
Properties
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

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
Algar-Flynn-Oyamada reaction


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. 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.
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