127034-55-3

Basic information

• Product Name: (2E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• Synonyms: (2E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS NO: 127034-55-3
• Molecular Formula: C₁₈H₁₈O₄
• Molecular Weight: 298.33312
• Mol File: 127034-55-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 139.0-140.5 °C
• Boiling Point: 449.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.139±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(127034-55-3)
• EPA Substance Registry System: (2E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(127034-55-3)

Safety Data

• Hazardous Substances Data: 127034-55-3(Hazardous Substances Data)

Upstream product

• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 201230-82-2 carbon monoxide 
• 477727-72-3 3,4,5-trimethoxy-β-iodostyrene 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 1082730-34-4 (E)-N-methoxy-N-methyl-3-(3,4,5-trimethoxyphenyl)acrylamide 
• 100-58-3 phenylmagnesium bromide 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 98-86-2 acetophenone 

Downstream Products

• 1296863-78-9 2,2-diethoxy-3-(3,4,5-trimethoxyphenyl)-5-phenyl-2,3-dihydrofuran 
• 1296863-85-8 ethyl 2-(3,4,5-trimethoxyphenyl)-4-oxo-4-phenylbutanoate 
• 1370046-40-4 3-phenyl-5-(3,4,5,-tri-OCH₃-phenyl)-4,5-dihydro 1H-pyrazole-1-carbothioamide 

Relevant articles and documents

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.

Triarylpyrazole Derivatives as Potent Cytotoxic Agents; Synthesis and Bioactivity Evaluation Pyrazole Derivatives as Anticancer Agent

Background During the last recent years, several anti-cancer agents were introduced for the treatment of diverse kinds of cancer. Despite their potential in the treatment of cancer, drug resistance and adverse toxicity such as peripheral neuropathy are so

Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities

Background: Chalcones substituted by methoxyl groups have presented a broad spec-trum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by chalcones substituted by methoxyl groups on rings A (5–12) and B (13–21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antipro-liferative agents. 3’, 4’, 5’-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 μg/mL), eight times more potent than fluconazole (reference antifungal drug). 3’-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 μg/mL). 2’,5’-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 μM. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 μM. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacte-rial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and phar-macokinetics properties to the library of methoxychalcones.