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T4080

Sigma-Aldrich

6, 2′, 4′-trimethoxyflavone

≥98% (HPLC)

Synonym(s):

2-(2,4-Dimethoxyphenyl)-2,3-dihydro-6-methoxy-4H-1-benzopyran-4-one, TMF, Trimethoxyflavone

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About This Item

Empirical Formula (Hill Notation):
C18H16O5
CAS Number:
720675-90-1
Molecular Weight:
312.32
MDL number:
MFCD03412381
UNSPSC Code:
12352200
PubChem Substance ID:
329826784
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

yellow

solubility

DMSO: >5 mg/mL

storage temp.

room temp

SMILES string

COc1ccc(c(OC)c1)C2=CC(=O)c3cc(OC)ccc3O2

InChI

1S/C18H16O5/c1-20-11-5-7-16-14(8-11)15(19)10-18(23-16)13-6-4-12(21-2)9-17(13)22-3/h4-10H,1-3H3

InChI key

WUWFDVDASNSUKP-UHFFFAOYSA-N

Biochem/physiol Actions

6, 2′, 4′-trimethoxyflavone is a selective aryl hydrocarbon receptor (AHR) antagonist with no partial agonist activity. The role of the transcription factor aryl hydrocarbon receptor (AHR) in biology is still under evaluation and has expanded beyond that of a xenobiotic sensor and regulator of detoxification. Inhibition of AHR activity by antagonists could result in anti-inflammatory actions. 6, 2′, 4′-trimethoxyflavone (TMF) is a pure AHR antagonist. The compound compete with agonists, such as 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin (TCDD) and benzo[a]pyrene (B[a]P), thus effectively inhibiting AHRmediated transactivation of a heterologous reporter and endogenous targets e.g. CYP1A1. TMF also exhibits no species or promoter dependency with regard to AHR antagonism. Thus it represents an improved tool allowing for more precise dissection of AHR function.
The AHR along with immune functions, is also associated with endocrine processes and cancer development.

Preparation Note

6, 2′, 4′-trimethoxyflavone is soluble in DMSO at a concentration that is greater than 5 mg/ml.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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