Irigenin

Irigenin
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	548-76-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81409^Y
ChemSpider	4576563
ECHA InfoCard	100.008.145
PubChem CID	5464170
UNII	6O4NX37350^Y
CompTox Dashboard (EPA)	DTXSID90203285
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,1-3H3 Key: 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 [77 °F], 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),^[1] and Iris kemaonensis.^[2]^[3]

Glycosides

Iridin is the 7-glucoside of irigenin.

References

^ 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
^ 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.
^ 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