-Trimethoxyflavone

Modify Date: 2024-01-28 12:28:45

-Trimethoxyflavone Structure
-Trimethoxyflavone structure
Common Name -Trimethoxyflavone
CAS Number 720675-74-1 Molecular Weight 312.317
Density 1.2±0.1 g/cm3 Boiling Point 495.2±45.0 °C at 760 mmHg
Molecular Formula C18H16O5 Melting Point N/A
MSDS N/A Flash Point 220.3±28.8 °C

 Use of -Trimethoxyflavone


6,2',4'-Trimethoxyflavone is a potent aryl hydrocarbon receptor (AHR) antagonist. 6,2',4'-Trimethoxyflavone represses AHR-mediated gene induction[1].

 Names

Name 2-(2,4-Dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
Synonym More Synonyms

 -Trimethoxyflavone Biological Activity

Description 6,2',4'-Trimethoxyflavone is a potent aryl hydrocarbon receptor (AHR) antagonist. 6,2',4'-Trimethoxyflavone represses AHR-mediated gene induction[1].
Related Catalog
In Vitro 6,2',4'-trimethoxyflavone (TMF) as an AHR ligand that possesses the characteristics of an antagonist having the capacity to compete with agonists, such as 2,3,7,8-tetrachlorodibenzo-p-dioxin and benzo[a]pyrene, thus effectively inhibiting AHR-mediated transactivation of a heterologous reporter and endogenous targets, e.g., CYP1A1, independent of cell lineage or species. Furthermore, TMF displays superior action by virtue of having no partial agonist activity, in contrast to other documented antagonists, e.g., alpha-napthoflavone, which are partial weak agonists. TMF also exhibits no species or promoter dependence with regard to AHR antagonism[1]. 6,2',4'-Trimethoxyflavone (0-100 μM; 72 hours) shows an inhibitory activity of TNF-⍺ production in THP-1 cells, with IC50 of 2.38 μM. 6,2',4'-Trimethoxyflavone shows an inhibitory activity of TNF-α production in B16-F10 cells with IC50 of 1.32 μM[2]. Cell Viability Assay[2] Cell Line: THP-1 cells, B16-F10 cells Concentration: 0-100 μM Incubation Time: 72 hours Result: Showed inhibitory activity of TNF-⍺ production in THP-1 cells and B16-F10 cells.
In Vivo 6,2',4'-trimethoxyflavone-treated (5 mg/kg/day; i.p.) WT mice shows significantly decreased infarct volume, improved sensorimotor, and nonspatial working memory functions compared with their respective controls[3]. Animal Model: Male C57BL/6 wild-type (WT) mice, AHRcKO mice[3] Dosage: 5 mg/kg/day Administration: I.p. Result: Both TMF-treated and AHRcKO mice attenuated acute cerebral infarction and functional impairments.
References

[1]. Murray IA, et al. Antagonism of aryl hydrocarbon receptor signaling by 6,2',4'-trimethoxyflavone [published correction appears in J Pharmacol Exp Ther. 2018 Nov;367(2):291]. J Pharmacol Exp Ther. 2010;332(1):135-144.

[2]. Apaza T L, et al. Flavonoids of Tripodanthus acutifolius inhibit TNF-α production in LPS-activated THP-1 and B16-F10 cells. J Ethnopharmacol. 2019;242:112036.

[3]. Chen WC, et al. Aryl hydrocarbon receptor modulates stroke-induced astrogliosis and neurogenesis in the adult mouse brain. J Neuroinflammation. 2019;16(1):187. Published 2019 Oct 12.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 495.2±45.0 °C at 760 mmHg
Molecular Formula C18H16O5
Molecular Weight 312.317
Flash Point 220.3±28.8 °C
Exact Mass 312.099762
LogP 3.54
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.585

 Synonyms

2-(2,4-Dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2-(2,4-dimethoxyphenyl)-6-methoxy-
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