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

• ChemBase ID: 154635
• Molecular Formular: C18H16O5
• Molecular Mass: 312.31664
• Monoisotopic Mass: 312.09977361
• SMILES: COc1ccc2c(c1)c(=O)cc(o2)c1ccc(cc1OC)OC
• Canonical SMILES: COc1ccc(c(c1)OC)c1cc(=O)c2c(o1)ccc(c2)OC
• InChI: 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
• InChIKey: WUWFDVDASNSUKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
• IUPAC Traditional name: 2-(2,4-dimethoxyphenyl)-6-methoxychromen-4-one
• Synonyms: 2-(2,4-Dimethoxyphenyl)-2,3-dihydro-6-methoxy-4H-1-benzopyran-4-one; TMF; Trimethoxyflavone; 6, 2′, 4′-trimethoxyflavone

Database IDs

• CAS Number: 720675-90-1
• MDL Number: MFCD03412381
• PubChem SID: 162248773
• PubChem CID: 688802

CALCULATED PROPERTIES

• Acid pKa: 15.155552
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.4943714
• LogD (pH = 7.4): 2.4943712
• Log P: 2.4943714
• Molar Refractivity: 86.3608 cm^3
• Polarizability: 32.825787 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: yellow powder

Safety Information

• Storage Condition: desiccated; protect from light
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H16O5

DETAILS

Sigma Aldrich - T4080

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.