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4',7-Dihydroxyflavone

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 254.241 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4′,7-Dihydroxyflavone is a flavone. It is found in Medicago truncatula in relation with the root nodulation symbiont Sinorhizobium meliloti[1] or in seeds of Sophora viciifolia.[2]

Like many other flavonoids, 4′,7-dihydroxyflavone has been found to possess activity at opioid receptors in vitro.[3] Specifically, it acts as an antagonist of the μ-opioid receptor and, with lower affinity, of the κ- and δ-opioid receptors.[3]

See also

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

References

  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. PMID 18786000.
  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. PMID 9206257.
  3. ^ a b Katavic 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. PMC 2265593. PMID 17685652.


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