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T4080

Sigma-Aldrich

6, 2′, 4′-trimethoxyflavone

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C18H16O5
Numéro CAS:
720675-90-1
Poids moléculaire :
312.32
Numéro MDL:
MFCD03412381
Code UNSPSC :
12352200
ID de substance PubChem :
329826784
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated
protect from light

Couleur

yellow

Solubilité

DMSO: >5 mg/mL

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

WUWFDVDASNSUKP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Samantha C Faber et al.
International journal of molecular sciences, 21(11) (2020-06-13)
1,2-naphthoquinone (1,2-NQ) and 1,4-naphthoquinone (1,4-NQ) are clinically promising biologically active chemicals that have been shown to stimulate the aryl hydrocarbon receptor (AhR) signaling pathway, but whether they are direct or indirect ligands or activate the AhR in a ligand-independent manner
Noël J Diepens et al.
Environmental science & technology, 52(15), 8510-8520 (2018-06-22)
We present a generic theoretical model (MICROWEB) that simulates the transfer of microplastics and hydrophobic organic chemicals (HOC) in food webs. We implemented the model for an Arctic case comprised of nine species including Atlantic cod and polar bear as
Joseph Shailender et al.
Drug development and industrial pharmacy, 44(7), 1109-1119 (2018-02-08)
Design chitosan based nanoparticles for tenofovir disoproxil fumarate (TDF) with the purpose of enhancing its oral absorption. TDF is a prodrug that has limited intestinal absorption because of its susceptibility to gut wall esterases. Hence, design of chitosan based polymeric
Runxia Sun et al.
Environmental pollution (Barking, Essex : 1987), 222, 165-174 (2017-01-04)
Short chain chlorinated paraffins (SCCPs) are under review for inclusion into the Stockholm Convention on Persistent Organic Pollutants. However, limited information is available on their bioaccumulation and biomagnification in ecosystems, which is hindering evaluation of their ecological and health risks.
Antagonism of aryl hydrocarbon receptor signaling by 6, 2?, 4?-trimethoxyflavone
Murray IA, et al.
Journal of Pharmacology and Experimental Therapeutics, 332(1), 135-144 (2010)
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