3-Hydroxyflavone

Quality 0.50 · 2 views · Updated 2 months ago

title: "3-Hydroxyflavone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["flavonols"] topic_path: "general/flavonols" source: "https://en.wikipedia.org/wiki/3-Hydroxyflavone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477218738 | Name = 3-Hydroxyflavone | ImageFile = Flavonol.svg | ImageAlt = Skeletal formula of 3-hydroxyflavone | ImageFile1 = 3-Hydroxyflavone-3D-balls.png | ImageAlt1 = Ball-and-stick model of the 3-hydroxyflavone molecule | IUPACName = 3-Hydroxyflavone | SystematicName = 3-Hydroxy-2-phenyl-4H-1-benzopyran-4-one | OtherNames= Flavon-3-ol 3-HF 3-Hydroxy-2-phenylchromone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 10871 | KEGG_Ref = | KEGG = C01495 | 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 | InChIKey = HVQAJTFOCKOKIN-UHFFFAOYAX | ChEMBL_Ref = | ChEMBL = 294009 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = HVQAJTFOCKOKIN-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 577-85-5 | UNII_Ref = | UNII = ZTG9LSS5QH | PubChem = 11349 | ChEBI_Ref = | ChEBI = 5078 | SMILES = O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3 |Section2={{Chembox Properties | Formula = C15H10O3 | MolarMass = 238.23 g/mol | Density = 1.367 g/mL | MeltingPt = | BoilingPt = 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. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/0e/Algar-Flynn-Oyamada_Reaction_Scheme.png" caption="Algar-Flynn-Oyamada reaction"] ::

References

References

  1. [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.]
  2. (1997). "Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.
  3. (2007). "Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects". International Journal of Biological Macromolecules.
  4. (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.
  5. (2011). "Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies". Journal of Molecular Structure.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

flavonols