| Identification | Back Directory | [Name]
6,7-DIMETHOXY-3',4',5-TRIHYDROXYFLAVONE | [CAS]
34334-69-5 | [Synonyms]
CIRSILIOL
Crisiliol
Cirsiliol >=95% (HPLC)
3'-Hydroxy-6-methoxygenkwanin
6-Methoxyluteolin 7-methyl ether
3',4',5-Trihydroxy-6,7-dimethoxy
6-Hydroxyluteolin-6,7-dimethyl ether
6,7-DIMETHOXY-3',4',5-TRIHYDROXYFLAVONE
6,7-DIMETHOXY-5,3',4'-TRIHYDROXYFLAVONE
6,7-DIMETHOXY-3,4'',5-TRIHYDROXYFLAVONE 95+% | [Molecular Formula]
C17H14O7 | [MDL Number]
MFCD00210577 | [MOL File]
34334-69-5.mol | [Molecular Weight]
330.29 |
| Chemical Properties | Back Directory | [Melting point ]
280-281.5℃ (methanol ) | [Boiling point ]
616.1±55.0 °C(Predicted) | [density ]
1.483±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Acetone: soluble; Chloroform: soluble; DMSO: soluble | [form ]
powder | [pka]
6.31±0.40(Predicted) | [color ]
white to beige | [InChI]
1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3 | [InChIKey]
IMEYGBIXGJLUIS-UHFFFAOYSA-N | [SMILES]
[o]1c2c([c](cc1c3cc(c(cc3)O)O)=O)c(c(c(c2)OC)OC)O |
| Hazard Information | Back Directory | [Uses]
Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand. | [Definition]
ChEBI: A dimethoxyflavone that is flavone substituted by methoxy groups at positions 6 and 7 and hydroxy groups at positions 5, 3' and 4' respectively. | [Biological Activity]
Cirsiliol is a flavonoid th at displays anti-inflammatoryanti-oxidantanti-proliferativeand anti-bacterial activities. Cirsiliol sensitizes non-small cell lung cancer cell lines (NSCLC) to radiation therapy. Cirsiliol inhibits epithelial-mesenchymal transition likely by induction of tumor-suppressive miR-34awhich suppresses Notch-1 expression NSCLC. | [in vivo]
In xenograft mouse model, tumor volume is significantly reduced by combinational treatment with irradiation and rhamnetin or cirsiliol compared with irradiation alone[2]. | [IC 50]
5-Lipoxygenase | [storage]
Store at -20°C | [References]
[1] Mustafa EH, et al. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated ileum. Gen Pharmacol. 1992 May;23(3):555-60. DOI:10.1016/0306-3623(92)90127-6
[2] Kang J, et al. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. J Biol Chem. 2013 Sep 20;288(38):27343-57. DOI:10.1074/jbc.M113.490482 |
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