4',7-DIMETHOXY-5-HYDROXYFLAVONE Chemical Properties

Melting point:

139-140 °C

Boiling point:

515.2±50.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO : 5 mg/mL (16.76 mM; Need ultrasonic)

form 

powder

pka

6.35±0.40(Predicted)

color 

Yellow

InChI

InChI=1S/C17H14O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-9,18H,1-2H3

InChIKey

LZERJKGWTQYMBB-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(OC)C=C2)OC2=CC(OC)=CC(O)=C2C(=O)C=1

LogP

3.444 (est)

4',7-DIMETHOXY-5-HYDROXYFLAVONE Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Uses

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]

Definition

ChEBI: A dimethoxyflavone that is the 7,4'-dimethyl ether derivative of apigenin.

IC 50

Human Endogenous Metabolite

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). DOI:10.1016/s0014-827x(00)00067-7
[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). DOI:10.1186/s12906-015-0934-7

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