6948-61-4

Basic information

• Product Name: (2E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one
• Synonyms: 2-propen-1-one, 1-(2-methoxyphenyl)-3-phenyl-, (2E)-
• CAS NO: 6948-61-4
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.2812
• Mol File: 6948-61-4.mol
• Article Data: 52

Chemical Properties

• Boiling Point: 398.8°C at 760 mmHg
• Flash Point: 181.3°C
• Density: 1.114g/cm³
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: (2E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one(6948-61-4)
• EPA Substance Registry System: (2E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one(6948-61-4)

Safety Data

• Hazardous Substances Data: 6948-61-4(Hazardous Substances Data)

Usage

Description

(2E)-1-(2-methoxyphenyl)-3-phenylprop-2-en-1-one, commonly known as chalcone, is an organic compound with the chemical formula C16H14O2. It belongs to the class of compounds known as chalconoids and is characterized by a yellow color. Chalcone is found in various plants, including licorice, shallots, and certain species of orchids.

Uses

Used in Pharmaceutical Industry:
Chalcone is used as an intermediate in the synthesis of numerous pharmaceuticals due to its diverse biological activities, including anti-inflammatory, anticancer, antioxidant, and antimicrobial properties. It has been studied for its potential in treating diseases such as cancer, diabetes, and neurodegenerative disorders.
Used in Agrochemical Industry:
Chalcone is used as a precursor in the synthesis of various agrochemicals, such as insecticides and fungicides, due to its biological activities.
Used in Dye Industry:
Chalcone is used in the synthesis of dyes due to its yellow color and chemical properties.

Upstream product

• 102-92-1 cinnamoyl chloride 
• 100-66-3 methoxybenzene 
• 579-74-8 2-Methoxyacetophenone 
• 100-52-7 benzaldehyde 
• 74-88-4 methyl iodide 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 59099-58-0 2-methoxyphenyl triflate 
• 100-51-6 benzyl alcohol 
• 644-78-0 2-hydroxychalcone 
• 77-78-1 dimethyl sulfate 
• 130824-68-9 1-((E)-1,1-Dimethoxy-3-phenyl-allyl)-2-methoxy-benzene 

Downstream Products

• 92208-78-1 (2-Methoxyphenyl)(c-2,t-3-diphenylcycloprop-r-1-yl)methanon 
• 92208-78-1 (2,3–diphenylcyclopropyl)(2–methoxyphenyl)methanone 
• 105473-13-0 2,4-bis(o-methoxybenzoyl)-3,5-diphenylthiolane 
• 60857-45-6 (2-methoxyphenyl)(3-phenyloxiran-2-yl)methanone 
• 883448-62-2 2-phenyl-6-(2-hydroxyphenyl)-4-phenylphosphinine 
• 1186044-41-6 diisopropyl 2-(3-(2-methoxyphenyl)-3-oxo-1-phenylpropyl)malonate 
• 61840-95-7 (2R,3S)-2,3-epoxy-1-(2-methoxyphenyl)-3-phenylpropan-1-one 
• 1237542-79-8 C₁₉H₂₀O₄S 
• 1255771-94-8 tert-butyl 3-(2-methoxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carboxylate 
• 1246850-10-1 N-((1R,2R)-2-bromo-3-(2-methoxyphenyl)-3-oxo-1-phenylpropyl)-4-methylbenzenesulfonamide 
• 1373121-98-2 1-(2-methoxyphenyl)-3-phenyl-3-(phenylthio)propan-1-one 
• 1426534-31-7 C₂₂H₁₉BrN₂O 

Relevant articles and documents

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

Synthesis of pyrazolopyrimidine derivatives along with its biological activity including toxicity studies

Pyrazolopyrimidines and related fused heterocycles are of interest as potential bioactive molecules. The heterocyclic fusion of pyrimidine ring and pyrazole ring resulted in formation of pyrazolopyrimidines, the structural analogues of biogenic purine class, undoubtedly, has high significance in the field of pharmaceutical and biotechnological sciences with wide spectrum of biological activities and its several derivatives. Toxicity may be due to the accumulation in a specific organ/ tissue (e.g. bosentan), the co - administration of other drugs affecting ADMET (absorption, distribution, metabolism, elimination and toxicity) Cmax reaching off target IC50, or the high Cmax required for therapeutic effects. Assessing the relative drug efficacy and toxicity is important for medicinal chemists, pharmacologists, pharmacists, physicians. As multiple treatment options are available for many diseases, relative toxicity assessment is necessary. Difficulty in direct clinical trial comparisons forces network meta-analyses for estimating the relative toxicity. Therapeutic index (TI) assumes simplified linear relationships between receptor affinity, maximum unbound plasma drug concentration (Cmax) and toxicity. But high TI does not guarantee safety. For drugs metabolized by cytochrome P450 (CYP450),estimating TI based on target potencies alone is insufficient.

Promising Non-cytotoxic Monosubstituted Chalcones to Target Monoamine Oxidase-B

A library of monosubstituted chalcones (1-17) bearing electron-donating and electron-withdrawing groups on both aromatic rings were selected. The cell viability on human tumor cell lines was evaluated first. The compounds unable to induce detectable cytotoxicity (1, 13, and 14) were tested using the monoamine oxidase (MAO) activity assay. Interestingly, they inhibit MAO-B, acting as competitive inhibitors, with 13 and 14 showing the best profiles. In particular, 13 exhibited a potency higher than that of safinamide, taken as a reference. Docking studies and crystallographic analysis showed that in human MAO-B 13 binds with the halogen-substituted aromatic ring in the entrance cavity, similar to safinamide, whereas 14 is accommodated in the opposite way. The main conclusion of this cell biology, biochemistry, and structural study is to highlights 13 as a chalcone derivative that is worth consideration for the development of novel MAO-B-selective inhibitors for the treatment of neurodegenerative diseases.