7,4'-Di-O-methylapigenin

Names

[ Name ]:
7,4'-Di-O-methylapigenin

[Synonym ]:
Genkwanin 4'-methyl ether
Flavone, 5-hydroxy-4',7-dimethoxy-
4',7-Dimethylapigenin
Apigenin dimethyl ether
7,4'-dimethylapigenin
5-Hydroxy-4',7-dimethoxyflavone
5-Hydroxy-4',7-dimethoxy-flavone
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
7,4'-di-O-methylapigenin
5-hydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
Apigenin 7,4'-dimethyl ether
4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2- (4-methoxyphenyl)-
Apigenin 4',7-dimethyl ether
4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-

Biological Activity

[Description]:

The compound 7,4'-Di-O-methylapigenin may be partly responsible for the reported antifungal activity of C. zeyheri, and may serve as a potential source of lead compounds that can be developed as antifungal phytomedicines.And it also showed inhibition of the drug efflux pumps (with IC50 = 51.64 μg/ml).IC50:51.64 μg/ml(Candida albicans drug efflux pumps)[2]In vitro: The isolated 7,4'-Di-O-methylapigenin was further investigated for its inhibitory activity on ABC drug efflux pumps in C. albicans by monitoring an increase in ciprofloxacin, assessing the level of its accumulation, in response to reserpine. There was a higher accumulation of ciprofloxacin in Candida cells in the presence of 7,4'-Di-O-methylapigenin than with reserpine. The compound 7,4'-Di-O-methylapigenine demonstrated the activity in a dose-dependent manner with IC50 value of 51.64 μg/ml. These results support those obtained from synergism assays where by the underlying synergistic antifungal mechanisms could be due to blockage of ABC efflux pumps and increasing the susceptibility of Candida to miconazole.[2]In vivo: In searching for natural products as potential anti-inflammatory agents, 7,4'-Di-O-methylapigenin wasn't evaluated in vivo for its ability to inhibit acute inflammation.[1]

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

Natural Products >> Flavonoids

[References]

[1]. Alvarez, M.E. et al.Phytochemical study and anti-inflammatory properties of Lampaya hieronymi Schum. ex Moldenke.Farmaco. Jun-Jul;55(6-7):502-5.doi:10.1016/S0014-827X(00)00067-7(2000).

[2]. Mangoyi, R., Midiwo, J. & Mukanganyama, S. Isolation and characterization of an antifungal compound 5-hydroxy-7,4'-dimethoxyflavone from Combretum zeyheri. BMC complementary and alternative medicine 15, 405, doi:10.1186/s12906-015-0934-7 (2015).

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
515.2±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₁₄O₅

[ Molecular Weight ]:
298.290

[ Flash Point ]:
193.3±23.6 °C

[ Exact Mass ]:
298.084137

[ PSA ]:
68.90000

[ LogP ]:
3.40

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.622

[ Storage condition ]:
-20℃

Safety Information

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

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%