T4080

6, 2′, 4′-trimethoxyflavone

≥98% (HPLC)

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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable