2373-79-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Ethoxycinnamic acid is used as an intermediate for the synthesis of cholest-5-en-3βyl 3-(4-ethoxyphenyl)-prop-2-enoate, which may have potential applications in the development of pharmaceuticals targeting specific health conditions. The compound's unique structure allows for further chemical modifications and exploration of its therapeutic properties.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-Ethoxycinnamic acid serves as a valuable building block for the synthesis of various complex organic molecules. Its reactivity and structural features make it a versatile compound for creating novel chemical entities with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
4-Ethoxycinnamic acid is utilized in research and development for studying its chemical properties, reactivity, and potential applications in various fields. Scientists and researchers can use 4-ETHOXYCINNAMIC ACID to explore new reaction pathways, develop innovative synthetic methods, and investigate its biological activities, which may lead to the discovery of new drugs or materials with beneficial properties.

InChI:InChI=1/C11H12O3/c1-2-14-10-6-3-9(4-7-10)5-8-11(12)13/h3-8H,2H2,1H3,(H,12,13)/p-1/b8-5+

Upstream product

• 141-82-2 malonic acid 
• 10031-82-0 4-ethoxybenzaldehyde 
• 7726-95-6 bromine 
• 71-43-2 benzene 
• 74-96-4 ethyl bromide 
• 7400-08-0 para-coumaric acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 108-24-7 acetic anhydride 
• 7400-08-0 p-Coumaric Acid 
• 75-00-3 chloroethane 
• 741272-25-3 5-((4-ethoxyphenyl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 87711-71-5 (E)-methyl-3-(4-ethoxyphenyl)prop-2-enoate 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 501-98-4 (Z)-p-coumaric acid 

Downstream Products

• 87711-71-5 (E)-methyl-3-(4-ethoxyphenyl)prop-2-enoate 
• 77251-75-3 3-(4-ethoxy-phenyl)-acryloyl chloride 
• 1357473-51-8 C₂₄H₂₆O₅ 
• 1394233-76-1 C₂₁H₂₀O₅ 
• 75332-46-6 (E)-ethyl 3-(4-ethoxyphenyl)acrylate 
• 77251-75-3 trans-p-ethoxycinnamoyl chloride 

Relevant academic research and scientific papers

“Effect of the linking unit on the calamitic-shaped liquid crystal: a comparative study of two homologous series of benzoate and cinnamate linked compounds”

Two homologous series based on three linking groups have been synthesized and well characterized by elemental analyses and spectroscopic techniques such as Fourier transform infrared [FT-IR] and proton magnetic resonance magnetic resonance [1H NMR] spectroscopy. The mesomorphic properties of these compounds were observed by using optical polarized microscopy (POM) and confirmed by differential scanning calorimetry (DSC) analysis. In this present investigation, we have synthesized two homologous series viz. (E)-4-(3-(4-(tetra decanoyloxy) phenyl) acryloyl) phenyl-4-n-alkoxy benzoate (Series-1) and 4-((E)-3-(4-(((E)-3-(4-n-alkoxy phenyl) acryloyl) oxy) phenyl)-3-oxo prop-1-en-1-yl) phenyl tetradecanoate (Series-2). Both of the series are differing with respect to the first linking group. All the homologous in following series displays LC properties on heating as well as cooling condition except first four homologous (C1 to C4) in series-1 and six homologous (C1 to C6) in series-2. To get more insights, the HOMO, LUMO studies are carried out which supports intramolecular charge transfer interactions in this class of mesogens.

Mesomorphism dependence on central bridge and tail ended polar group

A novel azoester homologous series of laterally and terminally substituted viz, RO–C6H4–CH=CH–COO–C6H3–(CH3) –N=N–C6H4–Cl is synthesized, characterized and studied with a view to understand and establish the relation between molecular structure and thermotropic liquid crystalline property of its homologs. Series consists of twelve homologs. LC properties commence from very first member of a series and continue up to last homolog as enantiotropic nematic with absence of smectic property even in the monotropic condition. Transition temperatures of homologs were determined by polarizing optical microscopy equipped with a heating stage. The transition curves Cr?N and N?I behaved in normal manner. Thermal stability for nematic is 196.7?C whose mesophaselength ranges from 35°C to 131°C.

Mesomorphism dependence on molecular rigidity and flexibility

A novel homologous series of liquid crystalline properties is synthesized and studied with a view to understand the effect of molecular structure on its thermotropic properties. Novel homologous series consisted of thirteen homologs. All the homologs are enantiotropically smectogenic with absence of nematic property even in the monotropic condition. Textures of the homologs as observed through an optical hot stage polarizing microscopy. The mesophase temperature range vary minimum from 6.0°C to a maximum 37.0°C at the methyloxy and propyloxy derivatives of a series respectively with its thermal stability (Sm–I) 127.0°C. Transition curves of a phase diagram behaved in normal manner. Odd–even effect is observed for Sm–I transition curve.

“Dependence of Mesomorphism in Combination with Fluoro and Chloro Groups”

A novel azoester homologous series with chloro lateral group and a fluoro terminal end group was synthesized and characterized for mesomorphic properties. It consists of thirteen azo ester derivatives from trans-4-n-alkoxy cinnamic acid with 4-hydroxy-3-chloro phenyl azo-3-chloro-4-fluoro benzene. Mesomorphic property commences from C4homologue as smectic.C1 to C3 member of the series are non-mesomorphic. C4 to C18 homologous are enantiotropic smectic A phase. The nematic mesophase is totally absent. Texture and transition temperatures of the homologues are determined by an optical polarizing microscopy equipped with heating stage. 1H NMR, IR spectra, mass spectra, of some member is included. The spectroscopic analysis supports the molecular structure. A phase diagram is used to illustrate the mesomorphic behaviour across the series. Mesophaselength for smectic is varying from18.0°C to 69.00C. Mesomorphic properties of the novel azoester series are compared with structurally similar series.

Synthesis, Crystallization Studies, and in vitro Characterization of Cinnamic Acid Derivatives as SmHDAC8 Inhibitors for the Treatment of Schistosomiasis

Schistosomiasis is a neglected parasitic disease that affects more than 265 million people worldwide and for which the control strategy relies on mass treatment with only one drug: praziquantel. Based on the 3-chlorobenzothiophene-2-hydroxamic acid J1075, a series of hydroxamic acids with different scaffolds were prepared as potential inhibitors of Schistosoma mansoni histone deacetylase 8 (SmHDAC8). The crystal structures of SmHDAC8 with four inhibitors provided insight into the binding mode and orientation of molecules in the binding pocket as well as the orientation of its flexible amino acid residues. The compounds were evaluated in screens for inhibitory activity against schistosome and human HDACs. The most promising compounds were further investigated for their activity toward the major human HDAC isotypes. The most potent inhibitors were additionally screened for lethality against the schistosome larval stage using a fluorescence-based assay. Two of the compounds showed significant, dose-dependent killing of the schistosome larvae and markedly impaired egg laying of adult worm pairs maintained in culture.

Molecular flexibility dependence on mesogenic behaviors of isomeric and nonisomeric series

A novel homologous series containing vinyl ester and azomethane central bridges and n-alkoxy as well as 3″,4″-dimethyl groups as flexible terminal/lateral groups viz. RO?C6H4?CH = CH?COO?C6H4?N?CH?C6H3-(CH3)2 have been synthesized and studied with a view to establishing the relation between molecular structure and thermotropic liquid crystal (LC) properties with reference to molecular flexibility within the series. The series consists of twelve homologues (C1 to C16). C6 and C7 homologues are smectogenic plus nematogenic and C8 to C16 homologues are only smectogenic, and the rest of the homologues (C1 to C5) are nonmesomorphic. Transition temperatures and the textures of the homologues were determined using an optical polarizing microscope equipped with a heating stage (POM). The textures of a nematic phase are threaded or Schlieren and that of a smectic phase are of the A or C type. Analytical, thermal and spectral data support the molecular structures. Smectic and nematic thermal stabilities are 116.85°C and 147.5°C, respectively. Whose Sm?N/I and N-I mesophase lengths are varied between 15°C to 21°C and 25°C to 62°C, respectively. The novel compounds are compared with structurally-similar series.

Synthesis, characterization, and mesomorphic investigation of vinyl ester-substituted chalcones and effect of lateral ?NO2 and ?OCH3 group

A novel homologous series of α-4-(4′-n-alkoxy cinnamoyloxy) phenyl β-2″-nitro, 3″–4″ di methoxy benzoyl ethylenes, H2n + 1CnO?C6H4?CH?CH?COO?C6H4?CO?CH?CH?C6H2(NO2) (OCH3)2 (n = 1–8, 10, 12, 14, 16, 18) has been synthesized. All these compounds have been characterized by suitable spectroscopic techniques. C1 homologue is nonmesogenic, while C2 homologue shows enantiotropic nematogenic property and the rest of the homologous (C3?C18) displayed enantiotropically smectogenic plus nematogenic phase. Phase transition temperatures and textures of the LC phase were determined by an optical polarizing microscopy (POM) equipped with a heating stage. The mesomorphic properties of these compounds were confirmed by differential scanning calorimetry (DSC) analysis.

Mesomorphic study of novel chalconyl-ester-based nonisomeric series: Synthesis and characterization

A newly designed homologues series: 3-(3-(4-(Dimethylamino) phenyl) acrylonyl) phenyl 3-(4-n-alkoxyphenyl) acrylate has been synthesized and studied through chalconyl ester linking group at (meta) position. The series consists of 13 compounds, in which C1 to C4 homologue are nonliquid crystal, while C5 to C18 exhibit nematic phase, and C12 to C18 shows smectic and nematic phase with enantiotropically manner. Mesophase image of present compounds are rod like, needle and threaded type textures investigated by POM. All this compounds were characterized by elemental analysis, FT-IR and 1H NMR. The mesomorphism is measured by POM, DSC, and molecular packing is determined by XRD technique. The following synthesized chalconyl ester-based compounds C5 to C12 shows antibacterial as well as antifungal activity compared with corresponding standard drugs. Analytical and spectral data confirmed the molecular structures of homologous series.

Study the effects of terminal side chain and –nitro group on mesomorphic behaviour of cinnamate-chalconyl based liquid crystal

The influence of the terminal side chain and lateral nitro on mesomorphism due to the flexibility and polarity of lateral group is investigated. A new homologues series is synthesized to accomplish this aim. The C1 to C3 homologue are nonmesomorphic, while the rest of the homologues exhibit enantiotropic nematic and smectic properties. The texture of the nematic mesophase is of threaded, Schlieren and droplets type. All these compounds were characterized by elemental analyses and spectroscopic techniques of FTIR and 1H Nuclear magnetic resonance (NMR). The phase behaviour was studied by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffraction techniques.

Tuning the mesomorphic properties of nonisomeric chalconyl-ester bases homologous series: The effect of tail group

The mesomorphic properties of nonlinear chalconyl ester homologous series can be tuned in a predictable fashion with tail groups (-OC16H33) substituents on the terminal side. Novel series consisted thirteen members (C1–C8, C10, C12, C14, C16, C18). C1 to C5 homologues are nonliquid crystal, C6 to C14 homologues shows nematic mesophase enantiotropically, while C16, C18 exhibits smectic as well nematic properties. The texture of the nematic mesophase is of fan shaped, schlieren and nematic droplets type. All these compounds were characterized by elemental analyses and spectroscopic techniques such as [FTIR] and 1H Nuclear magnetic resonance [NMR] spectroscopy. The mesomorphic properties of these compoundswere observed by optical polarized light microscopy (POM) and differential scanning calorimetry (DSC).