1657-65-4

Basic information

• Product Name: 2-(2-METHOXYPHENYL)-3-PHENYLACRYLIC ACID
• Synonyms: (E)-2-(2-METHOXYPHENYL)-3-PHENYL-2-PROPENOIC ACID;2-(2-METHOXYPHENYL)-3-PHENYLACRYLIC ACID
• CAS NO: 1657-65-4
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• Mol File: 1657-65-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 146-148°C
• Boiling Point: 374.2°Cat760mmHg
• Flash Point: 135.9°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 2.91E-06mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(2-METHOXYPHENYL)-3-PHENYLACRYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHOXYPHENYL)-3-PHENYLACRYLIC ACID(1657-65-4)
• EPA Substance Registry System: 2-(2-METHOXYPHENYL)-3-PHENYLACRYLIC ACID(1657-65-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1657-65-4(Hazardous Substances Data)

Usage

General Description

2-(2-Methoxyphenyl)-3-phenylacrylic acid, also known as p-methoxycinnamic acid, is a compound that belongs to the class of phenylpropanoids. It is a derivative of cinnamic acid and is commonly found in various plants and fruits. This chemical has been studied for its potential antioxidant, anti-inflammatory, and anti-microbial properties. It is also known to have potential applications in the pharmaceutical and cosmetic industries. Additionally, it is being researched for its potential use as a sunscreen agent due to its ability to absorb UV radiation. Overall, 2-(2-Methoxyphenyl)-3-phenylacrylic acid has a range of potential biological and industrial applications.

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

Upstream product

• 93-25-4 2-methoxyphenylacetic acid 
• 100-52-7 benzaldehyde 
• 1262329-34-9 C₁₆H₁₃ClO₃ 
• 93435-11-1 2-hydroxy-2-(2-methoxy-phenyl)-3-phenyl-propionic acid 
• 119460-67-2 Z-2-(o-methoxyphenyl)-3-phenyl propenoic acid 
• 23074-50-2 (o-Methoxyphenyl)-phenylcyclopropenon 

Downstream Products

• 119460-70-7 3-[1-phenyl-meth-(E)-ylidine]-3H-benzofuran-2-one 
• 1070183-48-0 2-(2-methoxyphenyl)-3-phenylpropionic acid 
• 1260509-97-4 2-(2-methoxyphenyl)-3-phenylpropionic acid 
• 1000394-61-5 2-(2-methoxyphenyl)-3-phenyl-propionic acid 
• 119460-71-8 (Z)-3-benzylidene-3H-benzofuran-2-one 

Relevant articles and documents

Surface enhanced Raman spectroscopic (SERS) behavior of substituted propenoic acids used in heterogeneous catalytic asymmetric hydrogenation

The strength and geometry of adsorption of substituted propenoic acids on silver surface were studied by means of surface enhanced Raman spectroscopy (SERS) using silver sol. Based on their SERS behavior, two classes of phenylpropenoic acids studied were distinguished. The first class of propenoic acids (atropic acid, (E)-2,3-diphenylpropenoic acid, (E)-2-(2-methoxyphenyl)-3-phenylpropenoic acid, (E)-2,3-di-(4-methoxyphenyl)phenylpropenoic acid and (E)-2-(2-methoxyphenyl)-3-(4-fluorophenyl)propenoic acid) has shown strong charge transfer (CT) effect. We suggest bidentate carboxyl bonded species based on the SERS enhanced bands of νCOO- around 1394 cm-1 and νC-C of the -C-COO- moiety at 951 cm-1. In these series the plane of the α-phenyl group (γCH out-of-plane vibrations at 850-700 cm-1) is almost parallel to the silver surface, while the β-phenyl group is in tilted position depending on the type and the position of substituent(s) showing strong SERS enhanced bands of νCC + βCH (in-plane mode) at 1075 cm-1, νCC (ring breathing mode, in-plane) at 1000 cm-1 and γCCC (out-of-plane mode) around 401 cm-1. The other class of propenoic acids (cinnamic acid, (E)-2-phenyl-3-(4-methoxyphenyl)propenoic acid) has shown weak electromagnetic (EM) enhancement (CC bands is enhanced in cinnamic acid). In this case no significant carboxyl enhancement was observed, so we suggest that adsorbed species lie parallel to the surface. The two types of adsorption can be related to the dissociation ability of the carboxylic group. In the first case the carboxylic H dissociates, while in the second case it does not, as indicated also by the characteristic νCO band at 1686 cm-1 in the FT-Raman spectra of methanolic solutions.

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.

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.