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D6571

Sigma-Aldrich

3′,4′-Dimethoxyflavone

Synonym(s):

2-(3,4-Dimethoxyphenyl)chromen-4-one, 3′,4′-DMF

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About This Item

Empirical Formula (Hill Notation):
C17H14O4
CAS Number:
4143-62-8
Molecular Weight:
282.29
MDL number:
MFCD00143009
UNSPSC Code:
12352200
PubChem Substance ID:
329798831
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

COc1ccc(cc1OC)C2=CC(=O)c3ccccc3O2

InChI

1S/C17H14O4/c1-19-15-8-7-11(9-17(15)20-2)16-10-13(18)12-5-3-4-6-14(12)21-16/h3-10H,1-2H3

InChI key

ZGHORMOOTZTQFL-UHFFFAOYSA-N

Application

3′,4′-Dimethoxyflavone has been used in urease inhibition assay.

Biochem/physiol Actions

3′,4′-Dimethoxyflavone is a flavone compound, which has the ability to prevent the production and accumulation of poly (ADP-ribose) (PAR) polymer. It guards against N-methyl-D-aspartate (NMDA) toxicity in cortical neurons. 3′,4′-Dimethoxyflavone is a member of the class of plant-derived polyphenolic flavonoids. It is known to have antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic and neuroprotective or neurotrophic effects.
3′,4′-dimethoxyflavone is a competitive antagonist of the AhR that inhibits AhR-mediated induction of CYP1A1, and also displays antiestrogen activity in breast tumor cell lines. The compound blocks transformation of the cytosolic AhR complex, and formation of nuclear AhR complexes.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

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

Certificates of Analysis (COA)

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Identification through high-throughput screening of 4'-methoxyflavone and 3', 4'-dimethoxyflavone as novel neuroprotective inhibitors of parthanatos
Fatokun AA, et al.
British Journal of Pharmacology, 169(6), 1263-1278 (2013)
Flavonoids as natural inhibitors of jack bean urease Enzyme
AJ Awllia, et al.
Letters in Drug Design & Discovery, 13(3), 243-249 (2016)
Nada H Eisa et al.
International journal of molecular sciences, 21(21) (2020-10-30)
There is increasing evidence of the involvement of the tryptophan metabolite kynurenine (KYN) in disrupting osteogenesis and contributing to aging-related bone loss. Here, we show that KYN has an effect on bone resorption by increasing osteoclastogenesis. We have previously reported
Dan J M Nguyen et al.
Molecular cancer research : MCR, 18(1), 105-117 (2019-10-20)
Cisplatin resistance is a major barrier in the effective treatment of lung cancer. Cisplatin-resistant (CR) lung cancer cells do not primarily use glucose but rather consume amino acids such as glutamine and tryptophan (Trp) for survival. CR cells activate the
Ke Wang et al.
International journal of molecular sciences, 16(7), 16454-16468 (2015-07-25)
Exposure to aristolochic acid I (AAI) can lead to aristolochic acid nephropathy (AAN), Balkan endemic nephropathy (BEN) and urothelial cancer. The induction of hepatic CYP1A, especially CYP1A2, was considered to detoxify AAI so as to reduce its nephrotoxicity. We previously

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