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Irilone

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Irilone
Chemical structure of irilone
Irilone molecule
Names
IUPAC name
4′,9-Dihydroxy-6,7-[methylenebis(oxy)]isoflavone
Preferred IUPAC name
9-Hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g][1]benzopyran-8-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2 ☒N
    Key: NUGRQNBDTZWXTP-UHFFFAOYSA-N ☒N
  • InChI=1/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2
    Key: NUGRQNBDTZWXTP-UHFFFAOYAV
  • C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)O)O
Properties
C16H10O6
Molar mass 298.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense (red clover),[1] in Iris unguicularis[2] and in Iris germanica.[3]

References

  1. ^ The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. Annett Braune, Ronald Maul, Nils Helge Schebb, Sabine E. Kulling and Michael Blaut, Molecular Nutrition & Food Research, 8 Dec 2009
  2. ^ New and Known Constituents from Iris unguicularis and Their Antioxidant Activity. Atta-ur-Rahman, Sumaira Hareem, M. Iqbal Choudhary, Bilge Sener, Ahmed Abbaskhan, Hina Siddiqui, Shazia Anjum, Ilkay Orhan, Ilhan Gurbuz and Filiz Ayanoglu, HeteroCycles, 2010, Special issue, Vol 82, No. 1, pages 813-824, doi:10.3987/COM-10-S(E)6
  3. ^ Lipase-catalyzed regioselective protection/deprotection of hydroxyl groups of the isoflavone irilone isolated from Iris germanica. Nighat Nazir, Surrinder Koul, Mushtaq Ahmad Qurishi, Subhash Chandra Taneja and Ghulam Nabi Qazi, Biocatalysis and Biotransformation, 2 December 2008, 1029-2446, Volume 27, Issue 2, Pages 118–123, INIST 21235726
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