irilone
{{Use dmy dates|date=February 2023}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 423620106
| Name = Irilone
| ImageFile = Irilone.svg
| ImageSize = 220px
| ImageName = Chemical structure of irilone
| ImageFile1 = Irilone-3D-balls.png
| ImageSize1 = 220
| ImageAlt1 = Irilone molecule
| IUPACName = 4′,9-Dihydroxy-6,7-[methylenebis(oxy)]isoflavone
| SystematicName = 9-Hydroxy-7-(4-hydroxyphenyl)-2H,8H-[1,3]dioxolo[4,5-g][1]benzopyran-8-one
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 41653-81-0
| CASNo_Ref = {{cascite|correct|??}}
| CASNoOther =
| PubChem = 5281779
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 5970
| SMILES = C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4445092
| 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
| InChIKey = NUGRQNBDTZWXTP-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NUGRQNBDTZWXTP-UHFFFAOYSA-N
| RTECS =
| MeSHName =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C10467
}}
|Section2={{Chembox Properties
| Formula = C16H10O6
| MolarMass = 298.24 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
}}
Irilone is an isoflavone, a type of flavonoid. It can be found in Trifolium pratense (red clover),[https://archive.today/20130105100639/http://www3.interscience.wiley.com/journal/123207380/abstract?CRETRY=1&SRETRY=0 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] in Iris unguicularisNew 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}} and in Iris germanica.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}}