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3′,4′-Dimethoxyflavone

Name: 3′,4′-Dimethoxyflavone
Brand: SIGMA

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

NACRES:

NA.77

PubChem Substance ID:

329798831

UNSPSC Code:

12352200

MDL number:

MFCD00143009

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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assay

≥98% (HPLC)

Quality Level

100

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

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This Item	SML0699	T4080	SML1052
Sigma-Aldrich D6571 3′,4′-Dimethoxyflavone	Sigma-Aldrich SML0699 4′-Methoxyflavone	Sigma-Aldrich T4080 6, 2′, 4′-trimethoxyflavone	Sigma-Aldrich SML1052 2-D08
assay ≥98% (HPLC)	assay ≥97% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form lyophilized powder	form powder	form powder
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. 2-8°C	storage temp. room temp	storage temp. 2-8°C
solubility DMSO: ≥20 mg/mL	solubility DMSO: 5 mg/mL, clear (warmed)	solubility DMSO: >5 mg/mL	solubility DMSO: 20 mg/mL, clear
color white to off-white	color white	color yellow	color white to beige

Application

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

Biochem/physiol Actions

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.

3′,4′-dimethoxyflavone is a competitive antagonist of the aryl hydrocarbon receptor (AhR) that inhibits AhR-mediated induction of CYP1A1, and also displays antiestrogen activity in breast tumor cell lines.

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.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

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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)

Targeting the Kynurenine Pathway for the Treatment of Cisplatin-Resistant Lung Cancer.

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

Kynurenine Promotes RANKL-Induced Osteoclastogenesis In Vitro by Activating the Aryl Hydrocarbon Receptor Pathway.

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

Baicalin Protects Mice from Aristolochic Acid I-Induced Kidney Injury by Induction of CYP1A through the Aromatic Hydrocarbon Receptor.

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

Global Trade Item Number

SKU	GTIN
D6571-5MG	04061832824185
D6571-25MG	04061832824178

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