Irigenin

Names

[ CAS No. ]:
548-76-5

[ Name ]:
Irigenin

[Synonym ]:
5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
7,5,3'-Trihydroxy-6,4',5'-trimethoxyisoflavon
5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone
Irigenin
EINECS 208-958-3

Biological Activity

[Description]:

Irigenin is a is a lead compound, and mediates its anti-metastatic effect by specifically and selectively blocking α9β1 and α4β1 integrins binding sites on C-C loop of Extra Domain A (EDA). Irigenin shows anti-cancer properties. It sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cytoskeleton >> Integrin

[In Vitro]

Irigenin specifically targets α9β1 and α4β1 integrin binding sites on Extra Domain A (EDA) comprising LEU46, PHE47, PRO48, GLU58, LEU59 and GLN60 in its C-C loop. Irigenin binds to the C-C loop of EDA, thereby blocking its interaction with integrins on the cell surface and thus abrogating subsequent Epithelial-Mesenchymal transition[1].

[References]

[1]. Amin A, et al. Irigenin, a novel lead from Western Himalayan chemiome inhibits Fibronectin-Extra Domain A induced metastasis in Lung cancer cells. Sci Rep. 2016 Nov 16;6:37151.

[2]. Xu Y, et al. Irigenin sensitizes TRAIL-induced apoptosis via enhancing pro-apoptotic molecules in gastric cancer cells. Biochem Biophys Res Commun. 2018 Feb 12;496(3):998-1005.

Chemical & Physical Properties

[ Density]:
1.461g/cm3

[ Boiling Point ]:
646.1ºC at 760mmHg

[ Melting Point ]:
189-192ºC

[ Molecular Formula ]:
C₁₈H₁₆O₈

[ Molecular Weight ]:
360.31500

[ Flash Point ]:
237.7ºC

[ Exact Mass ]:
360.08500

[ PSA ]:
118.59000

[ LogP ]:
2.60260

[ Index of Refraction ]:
1.649

[ Storage condition ]:
2-8C

Safety Information

[ HS Code ]:
2914509090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%