Genkwanin

Names

[ CAS No. ]:
437-64-9

[ Name ]:
Genkwanin

[Synonym ]:
5,4'-Dihydroxy-7-methoxyflavone
5-hydroxy-4',7-dimethoxyflavone
MFCD00017452
7-Methoxyapigenin
Gengkwanin
4',5-DIHYDROXY-7-METHOXYFLAVONE
7-O-methyl-naringenin
4′,5-Dihydroxy-7-methoxyflavone
7-O-Methylapigenin
Apigenin 7-methyl ether
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
5,14-dihydroxy-7-methoxyflavonone
Flavone, 4',5-dihydroxy-7-methoxy-
Genkwanin

Biological Activity

[Description]:

Genkwanin is a major non-glycosylated flavonoid with anti-flammatory activities.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[In Vitro]

Cell viability analysis shows that Genkwanin does not affect the cell viability up to a concentration of 50 μM. Genkwanin inhibits the LPS-induced production of NO in a concentration-dependent manner. iNOS only expresses in the present of external stimulus. Genkwanin could not significantly affect the activity of iNOS. The effect of Genkwanin on the production of proinflammatory cytokines is examined. Genkwanin suppresses the productions of TNF-a, IL-1b and IL-6 in LPS stimulated RAW264.7 macrophages in a concentration-dependent manner. Genkwanin significantly suppresses the AP-1 signaling pathway but has little effect on the NF-kB signaling pathway. It is indicated that Genkwanin suppresses the phosphorylation of p38 and JNK in a concentration-dependent manner, but little affects ERK1/2 phosphorylation. Originally identified as an immediate early gene, MKP-1 is then found to be a dual specificity phosphatase acting as a negative regulator of ERK1/2, JNK and p38 MAPK activities, with predominant effects on the latter two. Pretreatment with Genkwanin markedly up-regulates the expression of MKP-1 without affecting MKP-1 mRNA[1].

[References]

[1]. Gao Y et al. Genkwanin inhibits proinflammatory mediators mainly through the regulation of miR-101/MKP-1/MAPK pathway in LPS-activated macrophages. PLoS One. 2014 May 6;9(5):e96741.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
546.5±50.0 °C at 760 mmHg

[ Melting Point ]:
290-292°C

[ Molecular Formula ]:
C₁₆H₁₂O₅

[ Molecular Weight ]:
284.263

[ Flash Point ]:
209.7±23.6 °C

[ Exact Mass ]:
284.068481

[ PSA ]:
79.90000

[ LogP ]:
2.36

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.669

[ Storage condition ]:
Hygroscopic, -20?C Freezer, Under Inert Atmosphere

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

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%