| Revision as of 17:51, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443349600 of page 3-Hydroxyflavone for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 11:50, 13 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,619 edits Add: issue, bibcode. |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443348340 |
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| verifiedrevid = 477218738 |
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| Name = 3-Hydroxyflavone |
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| Name = 3-Hydroxyflavone |
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| ImageFile = Flavonol.svg |
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| ImageFile = Flavonol.svg |
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| ImageSize = 250px |
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| ImageName = 3-hydroxyflavone structure |
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| ImageAlt = Skeletal formula of 3-hydroxyflavone |
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| ImageFile1 = 3-Hydroxyflavone-3D-balls.png |
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| IUPACName = 3-hydroxy-2-phenylchromen-4-one |
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| ImageAlt1 = Ball-and-stick model of the 3-hydroxyflavone molecule |
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| OtherNames= 3-Hydroxyflavone<br>Flavon-3-ol<br>3-HF<br>3-Hydroxy-2-phenylchromone |
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| IUPACName = 3-Hydroxyflavone |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = 3-Hydroxy-2-phenyl-4''H''-1-benzopyran-4-one |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames= Flavon-3-ol<br>3-HF<br>3-Hydroxy-2-phenylchromone |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10871 |
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| ChemSpiderID = 10871 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 577-85-5 |
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| CASNo = 577-85-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 11349 |
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| UNII = ZTG9LSS5QH |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem = 11349 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 5078 |
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| ChEBI = 5078 |
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| SMILES = O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3 |
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| SMILES = O=C1c3c(O/C(=C1/O)c2ccccc2)cccc3 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>3</sub> |
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| Formula = C<sub>15</sub>H<sub>10</sub>O<sub>3</sub> |
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| MolarMass = 238.23 g/mol |
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| MolarMass = 238.23 g/mol |
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| ExactMass = 238.062994 |
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| Density = 1.367 g/mL |
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| MeltingPt = <!-- °C --> |
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'''3-Hydroxyflavone''' is a chemical compound. It is the backbone of all ]s, a type of ]. It is a synthetic compound, which is not found naturally in plants. It serves as a ] as it possesses an ] (ESIPT) effect<ref></ref> to serve as a fluorescent probe to study membranes for example<ref>{{cite journal | doi=10.1016/S1386-1425(96)01825-2 | volume=53 |issue = 3| title=Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes | year=1997 | journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy | pages=457–462 | last1 = Guharay | first1 = Jayanti | last2 = Chaudhuri | first2 = Rupali | last3 = Chakrabarti | first3 = Abhijit | last4 = Sengupta | first4 = Pradeep K.| bibcode=1997AcSpA..53..457G }}</ref> or intermembrane proteins.<ref>{{cite journal|last1=Chaudhuri|first1=Sudip|last2=Banerjee|first2=Anwesha|last3=Basu|first3=Kaushik|last4=Sengupta|first4=Bidisa|last5=Sengupta|first5=Pradeep K.|year=2007|title=Interaction of flavonoids with red blood cell membrane lipids and proteins: Antioxidant and antihemolytic effects|journal=International Journal of Biological Macromolecules|volume=41|issue=1 |pages=42–48|doi=10.1016/j.ijbiomac.2006.12.003|pmid=17239435}}{{cbignore|bot=medic}}</ref> The green tautomer emission (λ<sub>max</sub> ≈ 524 nm) and blue-violet normal emission (λ<sub>max</sub> ≈ 400 nm) originate from two different ground state populations of 3HF molecules.<ref>{{cite journal | doi=10.1016/0584-8539(95)01622-8 | volume=52 |issue = 2| title=Effect of reverse micelles on the intramolecular excited state proton transfer (ESPT) and dual luminescence behaviour of 3-hydroxyflavone | year=1996 | journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy | pages=275–278 | last1 = Sarkar | first1 = Munna | last2 = Guha Ray | first2 = Jayanti | last3 = Sengupta | first3 = Pradeep K.| bibcode=1996AcSpA..52..275S }}</ref> The phenomenon also exists in natural ]s. Although 3-hydroxyflavone is almost insoluble in water, its aqueous solubility (hence bio-availability) can be increased by encapsulation in cyclodextrin cavities.<ref>{{cite journal|doi=10.1016/j.molstruc.2011.09.055 | volume=1006 | issue=1–3 | title=Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies | year=2011 | journal=Journal of Molecular Structure | pages=483–488 | last1 = Pahari | first1 = Biswapathik | last2 = Chakraborty | first2 = Sandipan | last3 = Sengupta | first3 = Pradeep K.| bibcode=2011JMoSt1006..483P }}</ref> |
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==Synthesis== |
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The ] is a chemical reaction whereby a ] undergoes an oxidative cyclization to form a flavonol. |
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] |
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<!-- ==Glycosides== --> |
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==References== |
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{{Reflist}} |
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{{flavonol}} |
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{{DEFAULTSORT:Hydroxyflavone, 3-}} |
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] |