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4',7-Dihydroxyflavone

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4′,7-Dihydroxyflavone
Chemical structure of 4′,7-dihydroxyflavone
Names
IUPAC name
4′,7-Dihydroxyflavone
Systematic IUPAC name
7-Hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
7,4′-Dihydroxyflavone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H
    Key: LCAWNFIFMLXZPQ-UHFFFAOYSA-N
  • InChI=1/C15H10O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-8,16-17H
    Key: LCAWNFIFMLXZPQ-UHFFFAOYAD
  • C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C=C3)O)O
Properties
C15H10O4
Molar mass 254.241g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

4′,7-Dihydroxyflavoneis aflavone.It is found inMedicago truncatulain relation with the root nodulation symbiontSinorhizobium meliloti[1]or in seeds ofSophora viciifolia.[2]

Like many other flavonoids, 4′,7-dihydroxyflavone has been found to possess activity atopioid receptorsin vitro.[3]Specifically, it acts as anantagonistof theμ-opioid receptorand, with loweraffinity,of theκ-andδ-opioid receptors.[3]

See also[edit]

  • Pratol(7-hydroxy-4′-methoxyflavone) is theO-methylated form of the molecule.

References[edit]

  1. ^Zhang, Juan; Subramanian, Senthil; Stacey, Gary; Yu, Oliver (2009)."Flavones and flavonols play distinct critical roles during nodulation of Medicago truncatula by Sinorhizobium meliloti".The Plant Journal.57(1): 171–83.doi:10.1111/j.1365-313X.2008.03676.x.PMID18786000.
  2. ^Wang, X; Li, J; Wei, L; Ohmiya, S (1996). "Flavone constituents in the seeds of Sophora vicii folia Hance".Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica(in Chinese).21(3): 165–6, 191.PMID9206257.
  3. ^abKatavic PL, Lamb K, Navarro H, Prisinzano TE (August 2007)."Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships".J. Nat. Prod.70(8): 1278–82.doi:10.1021/np070194x.PMC2265593.PMID17685652.