13198-99-7

Basic information

• Product Name: 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
• Synonyms: 13198-99-7; 4H-1-benzopyran-4-one, 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-
• CAS NO: 13198-99-7
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.2901
• Mol File: 13198-99-7.mol

Chemical Properties

• Boiling Point: 476.8°C at 760 mmHg
• Flash Point: 177.2°C
• Density: 1.342g/cm³
• Vapor Pressure: 6.7E-10mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one(13198-99-7)
• EPA Substance Registry System: 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one(13198-99-7)

Safety Data

• Hazardous Substances Data: 13198-99-7(Hazardous Substances Data)

Upstream product

• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 24826-74-2 1-(4-methoxy-2-methylphenyl)ethanone 
• 123-11-5 4-methoxy-benzaldehyde 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 93175-94-1 7-methoxy-2-(4-methoxyphenyl)-3-nitro-2H-chromene 

Downstream Products

• 945991-48-0 3-(4-bromo-butoxy)-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 114050-92-9 3-(3-bromo-propoxy)-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 157077-01-5 Co(C₂H₄(NCHC₆H₄O)2)(C₉H₃O₃(OCH₃)C₆H₄OCH₃) 
• 2034-65-3 resokaempferol 
• 20979-40-2 3,7,4'-trimethoxyflavone 
• 1242087-54-2 C₂₃H₂₂O₁₁ 
• 1228174-43-3 methyl 5-hydroxy-2,5-methano-8-methoxy-2-(4-methoxyphenyl)-10-oxo-3-phenyl-2,3,4,5-tetrahydro-1-benzoxepin-4-carboxylate 
• 1227475-82-2 methyl 8b-hydroxy-6-methoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3-3a,8b-tetrahydro-cyclopenta[b]benzofuran-2-carboxylate 
• 1227475-62-8 rac-methyl (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate 
• 1096657-12-3 C₃₁H₃₂O₁₄ 
• 1096657-09-8 C₃₁H₃₂O₁₄ 
• 1096657-15-6 C₂₈H₂₈O₁₂ 

Relevant articles and documents

Design of Development Candidate eFT226, a First in Class Inhibitor of Eukaryotic Initiation Factor 4A RNA Helicase

Dysregulation of protein translation is a key driver for the pathogenesis of many cancers. Eukaryotic initiation factor 4A (eIF4A), an ATP-dependent DEAD-box RNA helicase, is a critical component of the eIF4F complex, which regulates cap-dependent protein synthesis. The flavagline class of natural products (i.e., rocaglamide A) has been shown to inhibit protein synthesis by stabilizing a translation-incompetent complex for select messenger RNAs (mRNAs) with eIF4A. Despite showing promising anticancer phenotypes, the development of flavagline derivatives as therapeutic agents has been hampered because of poor drug-like properties as well as synthetic complexity. A focused effort was undertaken utilizing a ligand-based design strategy to identify a chemotype with optimized physicochemical properties. Also, detailed mechanistic studies were undertaken to further elucidate mRNA sequence selectivity, key regulated target genes, and the associated antitumor phenotype. This work led to the design of eFT226 (Zotatifin), a compound with excellent physicochemical properties and significant antitumor activity that supports clinical development.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.

Profiling of flavonol derivatives for the development of antitrypanosomatidic drugs

Flavonoids represent a potential source of new antitrypanosomatidic leads. Starting from a library of natural products, we combined target-based screening on pteridine reductase 1 with phenotypic screening on Trypanosoma brucei for hit identification. Flavonols were identified as hits, and a library of 16 derivatives was synthesized. Twelve compounds showed EC50 values against T. brucei below 10 μM. Four X-ray crystal structures and docking studies explained the observed structure-activity relationships. Compound 2 (3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one) was selected for pharmacokinetic studies. Encapsulation of compound 2 in PLGA nanoparticles or cyclodextrins resulted in lower in vitro toxicity when compared to the free compound. Combination studies with methotrexate revealed that compound 13 (3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one) has the highest synergistic effect at concentration of 1.3 μM, 11.7-fold dose reduction index and no toxicity toward host cells. Our results provide the basis for further chemical modifications aimed at identifying novel antitrypanosomatidic agents showing higher potency toward PTR1 and increased metabolic stability.

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Isolation and synthesis of flavonols and comparison of their antioxidant activity

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COMPOUNDS FOR IMMUNOPOTENTIATION

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