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]
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| Names | |
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| IUPAC name
3-Hydroxyflavone
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| 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)
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| ChemSpider | |
| ECHA InfoCard | 100.008.562 |
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PubChem CID
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CompTox Dashboard (EPA)
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| 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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Synthesis
editThe Algar-Flynn-Oyamada reaction is a chemical reaction whereby a chalcone undergoes an oxidative cyclization to form a flavonol.
References
edit- ^ 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. Bibcode:1997AcSpA..53..457G. 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 (1): 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. Bibcode:1996AcSpA..52..275S. 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. Bibcode:2011JMoSt1006..483P. doi:10.1016/j.molstruc.2011.09.055.