6,2',4'-Trimethoxyflavone
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MedKoo CAT#: 463784

CAS#: 720675-74-1

Description: 6,2',4'-Trimethoxyflavone is a flavonoid that has been found in T. acutifolius and has diverse biological activities. It acts as an antagonist of the aryl hydrocarbon receptor (AhR), inhibiting benzo[a]pyrene-induced AhR-dependent transcription in a reporter assay when used at concentrations of 2 and 10 µM. 6,2',4'-Trimethoxyflavone decreases LPS-induced production of TNF-α in THP-1 cells. It inhibits cell migration and invasion, but not proliferation, of HN-30 head and neck squamous cell carcinoma (HNSCC) cells in vitro when used at a concentration of 10 µM.


Chemical Structure

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6,2',4'-Trimethoxyflavone
CAS# 720675-74-1

Theoretical Analysis

MedKoo Cat#: 463784
Name: 6,2',4'-Trimethoxyflavone
CAS#: 720675-74-1
Chemical Formula: C18H16O5
Exact Mass: 312.0998
Molecular Weight: 312.321
Elemental Analysis: C, 69.22; H, 5.16; O, 25.61

Price and Availability

Size Price Availability Quantity
10.0mg USD 240.0 2 Weeks
50.0mg USD 480.0 2 Weeks
250.0mg USD 800.0 2 Weeks
500.0mg USD 1390.0 2 Weeks
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Synonym: 6,2',4'-Trimethoxyflavone; 6,2',4' Trimethoxyflavone;

IUPAC/Chemical Name: 2-(2,4-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one

InChi Key: WUWFDVDASNSUKP-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: O=C1C2=CC(OC)=CC=C2OC(C3=CC=C(OC)C=C3OC)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 312.321 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Apaza Ticona L, Bermejo P, Guerra JA, Abad MJ, Beltrán M, Martín Lázaro R, Alcamí J, Bedoya LM. Ethanolic extract of Artemisia campestris subsp. glutinosa (Besser) Batt. inhibits HIV-1 replication in vitro through the activity of terpenes and flavonoids on viral entry and NF-κB pathway. J Ethnopharmacol. 2020 Dec 5;263:113163. doi: 10.1016/j.jep.2020.113163. Epub 2020 Aug 3. PMID: 32758575; PMCID: PMC7397943.

2: Chen WC, Chang LH, Huang SS, Huang YJ, Chih CL, Kuo HC, Lee YH, Lee IH. Aryl hydrocarbon receptor modulates stroke-induced astrogliosis and neurogenesis in the adult mouse brain. J Neuroinflammation. 2019 Oct 12;16(1):187. doi: 10.1186/s12974-019-1572-7. PMID: 31606043; PMCID: PMC6790016.

3: Scobie MR, Houke HR, Rice CD. Modulation of glioma-inflammation crosstalk profiles in human glioblastoma cells by indirubin-3'-(2,3 dihydroxypropyl)-oximether (E804) and 7-bromoindirubin-3'-oxime (7BIO). Chem Biol Interact. 2019 Oct 1;312:108816. doi: 10.1016/j.cbi.2019.108816. Epub 2019 Sep 7. PMID: 31505164.

4: Apaza T L, Serban AM, Cabanillas AH, Villacampa A, Rumbero A. Flavonoids of Tripodanthus acutifolius inhibit TNF-α production in LPS-activated THP-1 and B16-F10 cells. J Ethnopharmacol. 2019 Oct 5;242:112036. doi: 10.1016/j.jep.2019.112036. Epub 2019 Jun 22. PMID: 31238104.

5: Correction to "Antagonism of Aryl Hydrocarbon Receptor Signaling by 6, 2',4'-Trimethoxyflavone". J Pharmacol Exp Ther. 2018 Nov;367(2):291. doi: 10.1124/jpet.109.158261err. Erratum for: J Pharmacol Exp Ther. 2010 Jan;332(1):135-44. PMID: 30305307; PMCID: PMC6202835.

6: Poormasjedi-Meibod MS, Salimi Elizei S, Leung V, Baradar Jalili R, Ko F, Ghahary A. Kynurenine Modulates MMP-1 and Type-I Collagen Expression Via Aryl Hydrocarbon Receptor Activation in Dermal Fibroblasts. J Cell Physiol. 2016 Dec;231(12):2749-60. doi: 10.1002/jcp.25383. Epub 2016 Apr 4. PMID: 26992058.

7: Xiao W, Son J, Vorrink SU, Domann FE, Goswami PC. Ligand-independent activation of aryl hydrocarbon receptor signaling in PCB3-quinone treated HaCaT human keratinocytes. Toxicol Lett. 2015 Mar 18;233(3):258-66. doi: 10.1016/j.toxlet.2015.02.005. Epub 2015 Feb 7. PMID: 25668756; PMCID: PMC4341842.

8: Cuartero MI, Ballesteros I, de la Parra J, Harkin AL, Abautret-Daly A, Sherwin E, Fernández-Salguero P, Corbí AL, Lizasoain I, Moro MA. L-kynurenine/aryl hydrocarbon receptor pathway mediates brain damage after experimental stroke. Circulation. 2014 Dec 2;130(23):2040-51. doi: 10.1161/CIRCULATIONAHA.114.011394. Epub 2014 Oct 30. PMID: 25359166.

9: Wang Q, Chen J, Ko CI, Fan Y, Carreira V, Chen Y, Xia Y, Medvedovic M, Puga A. Disruption of aryl hydrocarbon receptor homeostatic levels during embryonic stem cell differentiation alters expression of homeobox transcription factors that control cardiomyogenesis. Environ Health Perspect. 2013 Nov- Dec;121(11-12):1334-43. doi: 10.1289/ehp.1307297. Epub 2013 Sep 20. PMID: 24058054; PMCID: PMC3855521.

10: DiNatale BC, Smith K, John K, Krishnegowda G, Amin SG, Perdew GH. Ah receptor antagonism represses head and neck tumor cell aggressive phenotype. Mol Cancer Res. 2012 Oct;10(10):1369-79. doi: 10.1158/1541-7786.MCR-12-0216. Epub 2012 Aug 21. PMID: 22912337; PMCID: PMC3477495.

11: Zhao B, Degroot DE, Hayashi A, He G, Denison MS. CH223191 is a ligand- selective antagonist of the Ah (Dioxin) receptor. Toxicol Sci. 2010 Oct;117(2):393-403. doi: 10.1093/toxsci/kfq217. Epub 2010 Jul 15. PMID: 20634293; PMCID: PMC2940411.

12: Murray IA, Flaveny CA, DiNatale BC, Chairo CR, Schroeder JC, Kusnadi A, Perdew GH. Antagonism of aryl hydrocarbon receptor signaling by 6,2',4'-trimethoxyflavone. J Pharmacol Exp Ther. 2010 Jan;332(1):135-44. doi: 10.1124/jpet.109.158261. Epub 2009 Oct 14. Erratum in: J Pharmacol Exp Ther. 2018 Nov;367(2):291. PMID: 19828881; PMCID: PMC2802483.