?-Naphthoflavone

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?-Naphthoflavone

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Cat No: 16924

Biochemicals - Natural Products

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2.{12907} α-Naphth...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

2-phenyl-4H-naphtho[1,2-b]pyran-4-one

Correlated keywords:

biochemical receptor antagonist inhibitor agonist toxicology cytochrome P450 gene regulation transcription factor flavone xenobiotic metabolism aryl hydrocarbon receptor AhR ligand-activated expression phase I II chemical metabolizing enzyme CYP isoform CYP1A1 CYP1A2 1A1 1A2 antagonize blocking agonize inhibit CYP19 aromatase CYP1B1 1B1 CYP3A4 3A4 dietary carcinogenesis synthetic estrogen NSC407011 ?-Naphthylflavone ANF benzo[h]flavone UCCF023 UCCF 023

Product Overview:
The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2.{12907} α-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 µM).{27487,27488} α-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 µM).{27489,27484,27486} Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.{27485}

Size	1 g
Shipping	dry ice
CAS Number	604-59-1
Molecular Formula	C₁₉H₁₂O₂
SMILES	O=C1C2=C(C(C=CC=C3)=C3C=C2)OC(C4=CC=CC=C4)=C1
Molecular Weight	272,3
Formulation	A crystalline solid
Purity	≥98%
Custom Code	2932.99
UNSPSC code	12352100

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

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ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.