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Usage

Uses

Used in Pharmaceutical Research:
3-(2-Methoxyphenyl)-2-phenylacrylic acid is used as a pharmaceutical candidate for its potential biological activity. Its antioxidant and anti-inflammatory properties make it a valuable compound for the development of treatments for various diseases and conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(2-Methoxyphenyl)-2-phenylacrylic acid serves as a key intermediate for the synthesis of various organic compounds. Its unique structure and reactivity contribute to the creation of new molecules with potential applications in various industries.
Used in Antioxidant Applications:
3-(2-Methoxyphenyl)-2-phenylacrylic acid is used as an antioxidant in various applications, including food preservation, cosmetics, and pharmaceuticals. Its ability to neutralize free radicals and protect against oxidative stress makes it a valuable ingredient in these industries.
Used in Anti-Inflammatory Applications:
Due to its anti-inflammatory properties, 3-(2-Methoxyphenyl)-2-phenylacrylic acid is used in the development of treatments for inflammatory conditions. Its potential to reduce inflammation and alleviate symptoms makes it a promising candidate for therapeutic applications in this area.

InChI:InChI=1/C16H14O3/c1-19-15-10-6-5-9-13(15)11-14(16(17)18)12-7-3-2-4-8-12/h2-11H,1H3,(H,17,18)/b14-11+

Upstream product

• 955-10-2 3-phenylcumarin 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 103-82-2 phenylacetic acid 
• 135-02-4 ortho-anisaldehyde 
• 23074-50-2 (o-Methoxyphenyl)-phenylcyclopropenon 
• 93432-78-1 (E)-3-(2-hydroxyphenyl)-2-phenyl-prop-2-enoic acid 

Downstream Products

• 1839-72-1 2-phenylbenzofuran 
• 73867-37-5 3-(acetoxymethyl)-2-phenylbenzofuran 
• 73867-38-6 2-acetoxy-1-phenyl-2-(2-methoxyphenyl)ethanone 
• 73867-39-7 5-acetoxy-4-(2-methoxyphenyl)-5-phenyl-2(5H)-furanone 
• 52805-92-2 (E)-2-methoxystilbene 
• 943317-83-7 C₂₆H₂₅NO₃ 
• 943317-75-7 C₂₆H₂₇NO₄ 
• 1070183-56-0 2-phenyl-3-(2-methoxyphenyl)propionic acid 
• 73867-61-5 2-acetoxy-2-phenyl-3(2H)-furanone 
• 42307-45-9 methyl (E)-3-(2-methoxyphenyl)-2-phenylacrylate 
• 18493-15-7 (E)-2-hydroxystilbene 
• 1898-14-2 (Z)-1-(2-methoxyphenyl)-2-phenylethene 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of compounds with a new scaffold as anti-neuroinflammatory agents for the treatment of Alzheimer's disease

Twenty-eight compounds with a new scaffold were designed and synthesized by assembling fragments derived from known agents such as stilbenes and piperazinyl pyrimidines. Many strategies have been explored to improve the druggability of these series of compounds, such as increasing the distance between two benzene rings in the scaffold and introducing functional groups at designated positions. These compounds were validated for their anti-neuroinflammatory activity in BV2 cells. Experimental results reveal that the most active compound 8b can inhibit nitric oxide (NO), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) production with IC50 values of 1.0, 2.6, and 0.5 μM, respectively. The compound can also significantly modulate the MAPK pathways through inhibiting the phosphorylation of JNK, ERK1/2, and p38 MAPK without disturbing NF-κB pathway. Parallel artificial membrane permeation assay demonstrated that the most active compound can overcome the blood-brain barrier (BBB). Therefore, this compound can be a promising lead for the treatment of Alzheimer's disease.

Synthesis of E- and Z-o-methoxy-substituted 2,3-diphenyl propenoic acids and its methyl esters

A series of stereoisomeric o-methoxy-substituted 2,3-diphenyl propenoic acids and their methyl esters have been synthesized. The E isomers were prepared by a modified Perkin condensation (substituted benzaldehyde, phenylacetic acid, Et3N/acetic anhydride). The difficult to access Z isomers were obtained conveniently in good yields when the appropriate coumarin derivatives were allowed to react with KOH and CH3I in DMSO.

Reactions of carbonyl compounds in basic solutions. Part 34. The mechanism of the base-catalysed ring fission of 2,3-diphenylcycloprop-2-en-1-one

The rate coefficients for the base-catalysed ring fission of a series of 2-phenyl-3-(2-, 3-or 4-substituted phenyllcycloprop-2-en-1-ones to give the corresponding (E)-2,3-diphenylacrylic acids have heen determined in water at 30.0 °C, as well as for the unsubstituted compound at 40.0, 50.0 and 60.0 °C. The effects of meta-and para-substituents on the rates have been correlated using the Hammett equation to give a reaction constant, p, equal to ca 1.2 at 30 °C. For the unsubstituted compound, the activation parameters have been calculated and the kinetic solvent isotope effect has been studied. The effects of ortho-substituents on the rates appear to be mainly polar, rather than steric, in origin. The evidence indicates a mechanistic pathway which proceeds by addition of hydroxide anion to the ketone, which is rate-determining. The adduct suffers ring fission to give the final product via a carbanionic intermediate.

Protonation and ring closure of stereoisomeric α-substituted cinnamic acids in superacidic media studied by 13C NMR spectroscopy and computations

Five α-substituted cinnamic acids [(E)- and (Z)-2,3-diphenyl-, (E)- and (Z)-3-(2-methoxyphenyI)-2-phenyl- and (E)-2-(2-methoxyphenyl)-3-phenyl-propenoic acids] have been protonated in fluorosulfonic acid at -78°C. Protonation of the carboxylic group and a second protonation on the methoxy group at -78°C or the ring bearing the methoxy group at 0°C have been observed by 13C NMR spectroscopy. Upon protonation (Z)-α-phenylcinnamic acid is transformed to a protonated indenol derivative. Dehydrative ring closure begins at -78°C and goes to completion at 0°C. Similar transformations of the other studied Z-acid are suppressed by the deactivating effect of the protonated methoxy group. Only protonation has been observed for the E-acids at -78°C as well as 0°lculations at the HF/3-21G level provide the equilibrium structures of the corresponding cations. Results of IGLO/13C NMR shift calculations are in good agreement with the experimental findings.

The Oxidation of (E)-α-Phenylcinnamic Acids with Manganese(III) Acetate

The oxidation of eight (E)-α-phenylcinnamic acids with manganese(III) acetate in boiling acetic acid containing acetic anhydride gave 3-phenylcoumarins, 3-phenyl-1-oxaspirodeca-3,7,9-triene-2,6-diones, 2-phenylbenzofurans, 3-(acetoxymethyl)-2-phenylbenzofurans, 3-formyl-2-phenylbenzofuran, 2-acetoxy-2-phenyl-3(2H)-benzofuranones, (Z)-Α-acetoxystilbenes, 2-acetoxy-1,2-diphenylethanones, 5-acetoxy-4,5-diphenyl-2(5H)-furanones, and diphenylacetylene.Tha reaction pathways are discussed.