20890-72-6

Basic information

• Product Name: 3-(2-METHOXYPHENYL)-2-PHENYLACRYLIC ACID
• Synonyms: 3-(2-METHOXYPHENYL)-2-PHENYLACRYLIC ACID;(E)-3-(2-METHOXYPHENYL)-2-PHENYL-2-PROPENOIC ACID
• CAS NO: 20890-72-6
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Mol File: 20890-72-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 187-189°C
• Boiling Point: 374.2°C at 760 mmHg
• Flash Point: 135.9°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 2.91E-06mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 3-(2-METHOXYPHENYL)-2-PHENYLACRYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-METHOXYPHENYL)-2-PHENYLACRYLIC ACID(20890-72-6)
• EPA Substance Registry System: 3-(2-METHOXYPHENYL)-2-PHENYLACRYLIC ACID(20890-72-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20890-72-6(Hazardous Substances Data)

Usage

General Description

3-(2-Methoxyphenyl)-2-phenylacrylic acid is a compound with the chemical formula C16H14O3. It is a member of the acrylate family and contains a phenylacrylic acid group. This chemical is often used in organic synthesis and pharmaceutical research due to its potential biological activity. It is also known by the name "ferulic acid" and can be found in various plants, particularly in seeds and leaves. Research has shown that 3-(2-Methoxyphenyl)-2-phenylacrylic acid possesses antioxidant and anti-inflammatory properties, making it a potential candidate for therapeutic applications in the treatment of various diseases and conditions.

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

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

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 
• 73867-61-5 2-acetoxy-2-phenyl-3(2H)-furanone 
• 1070183-56-0 2-phenyl-3-(2-methoxyphenyl)propionic acid 
• 943317-83-7 C₂₆H₂₅NO₃ 
• 943317-75-7 C₂₆H₂₇NO₄ 
• 42307-45-9 methyl (E)-3-(2-methoxyphenyl)-2-phenylacrylate 
• 18493-15-7 (E)-2-hydroxystilbene 

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.