21140-85-2

Basic information

• Product Name: (2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid
• Synonyms: (2-methoxybenzylidene)phenylacetic acid; 3-(2-Methoxy-phenyl)-2-phenyl-acrylic acid; 3-(o-Methoxyphenyl)-2-phenylacrylic acid; Acrylic acid, 3- (o-methoxyphenyl)-2-phenyl-; a-Phenyl-o-methoxycinnamic Acid; b-(o-Methoxyphenyl)-a-phenylacrylic Acid
• CAS NO: 21140-85-2
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.2806
• Mol File: 21140-85-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 374.2°C at 760 mmHg
• Flash Point: 135.9°C
• Density: 1.204g/cm³
• Vapor Pressure: 2.91E-06mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: (2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid(21140-85-2)
• EPA Substance Registry System: (2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid(21140-85-2)

Safety Data

• Hazardous Substances Data: 21140-85-2(Hazardous Substances Data)

Usage

General Description

"(2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid" is a chemical compound with the molecular formula C17H14O3. It is also known by the name "o-Methoxyphenyl Acrylic Acid" and is a derivative of acrylic acid. (2E)-3-(2-methoxyphenyl)-2-phenylprop-2-enoic acid is used in various industrial applications, including as a building block in the synthesis of pharmaceuticals and other organic compounds. It is also used in the production of polymers and other materials. In addition, it has potential biological and pharmacological activities, making it of interest for research and development in the medical and pharmaceutical fields.

Upstream product

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

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 
• 42307-45-9 methyl (E)-3-(2-methoxyphenyl)-2-phenylacrylate 
• 1070183-56-0 2-phenyl-3-(2-methoxyphenyl)propionic acid 
• 52805-92-2 (E)-2-methoxystilbene 
• 73867-61-5 2-acetoxy-2-phenyl-3(2H)-furanone 
• 18493-15-7 (E)-2-hydroxystilbene 
• 1898-14-2 (Z)-1-(2-methoxyphenyl)-2-phenylethene 

Relevant articles and documents

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.

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.

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.