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Irigenin

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Irigenin
Irigenin molecule
Names
IUPAC name 3′,5,7-Trihydroxy-4′,5′,6-trimethoxyisoflavone
Systematic IUPAC name 5,7-Dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.145 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3Key: TUGWPJJTQNLKCL-UHFFFAOYAF
SMILES
  • O=C\1c3c(O)c(OC)c(O)cc3O/C=C/1c2cc(O)c(OC)c(OC)c2
Properties
Chemical formula C18H16O8
Molar mass 360.31 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis.

Glycosides

Iridin is the 7-glucoside of irigenin.

References

  1. Inhibitory effects of Irigenin from the rhizomes of Belamcanda chinensis on nitric oxide and prostaglandin E2 production in murine macrophage RAW 264.7 cells. Kwang Seok Ahn, Eun Jung Noh, Kwang-Hyun Cha, Yeong Shik Kim, Soon Sung Lim, Kuk Hyun Shin and Sang Hoon Jung, 2005
  2. Mahmooda, Umar; Kaula, Vijay K.; Jirovetzb, Leopold (December 2002). "Alkylated benzoquinones from Iris kumaonensis". Phytochemistry. 61 (8): 923–926. Bibcode:2002PChem..61..923M. doi:10.1016/S0031-9422(02)00474-0. PMID 12453518.
  3. Jiaju Zhou, Guirong Xie and Xinjian Yan Encyclopedia of Traditional Chinese Medicines - Molecular Structures, Pharmalogical Activities, Natural sources and Applications, p. 214, at Google Books
Isoflavones and their glycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
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