14813-19-5

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-
• Synonyms: 4H-1-Benzopyran-4-one, 2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-;2-(2,6-Dimethoxyphenyl)-5,6-dimethoxy-4H-1-benzopyran-4-one;2′,5,6,6′-Tetramethoxyflavone;3.7.2-(3-Hydroxy-4,5-dimethoxyphenyl)-4H-1- benzopyran-4-one;2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-4H-chromen-4-one
• CAS NO: 14813-19-5
• Molecular Formula: C₁₉H₁₈O₆
• Molecular Weight: 342.34
• Mol File: 14813-19-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-(14813-19-5)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-(2,6-dimethoxyphenyl)-5,6-dimethoxy-(14813-19-5)

Safety Data

• Hazardous Substances Data: 14813-19-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 50, p. 350, 2007 DOI: 10.1021/jm060915+

Upstream product

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Relevant articles and documents

CHEMOTHERAPEUTIC FLAVONOIDS, AND SYNTHESES THEREOF

Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.

Synthesis and cancer chemopreventive activity of zapotin, a natural product from Casimiroa edulis

An efficient method has been developed to synthesize zapotin (5,6,2′,6′-tetramethoxyflavone), a component of the edible fruit Casimiroa edulis, on a multigram scale. The synthesis utilizes a regioselective C-acylation of a dilithium dianion derived from a substituted o-hydroxyactophenone to afford a β-diketone intermediate that can be cyclized to zapotin in good overall yield, thus avoiding the inefficient Baker-Venkataraman rearrangement pathway. Zapotin was found to induce both cell differentiation and apoptosis with cultured human promyelocytic leukemia cells (HL-60 cells). In addition, the compound inhibits 12-O-tetrade-canoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity with human bladder carcinoma cells (T24 cells), and TPA-induced nuclear factor-kappa B (NF-κB) activity with human hepatocellular liver carcinoma cells (HepG2 cells). These data suggest that zapotin merits further investigation as a potential cancer chemopreventive agent.