127427-28-5

Basic information

• Product Name: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE
• Synonyms: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE
• CAS NO: 127427-28-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.25
• Mol File: 127427-28-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 358.2°C at 760 mmHg
• Flash Point: 158.1°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 2.6E-05mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(127427-28-5)
• EPA Substance Registry System: (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE(127427-28-5)

Safety Data

• Hazardous Substances Data: 127427-28-5(Hazardous Substances Data)

Usage

General Description

The chemical (E)-ethyl 4-(4-methoxyphenyl)-4-oxobut-2-enoate, also known as ethyl 4-(4-methoxyphenyl)-2-oxobut-3-enoate, is an organic compound with the molecular formula C13H14O4. It is a derivative of 4-methoxycinnamic acid and is commonly used in organic synthesis and medicinal chemistry. (E)-ETHYL 4-(4-METHOXYPHENYL)-4-OXOBUT-2-ENOATE is a yellowish liquid with a fruity odor and is soluble in organic solvents. It has applications in the production of pharmaceuticals, fragrances, and flavorings. Additionally, it has demonstrated potential pharmacological properties, including anti-inflammatory effects.

InChI:InChI=1/C13H14O4/c1-3-17-13(15)9-8-12(14)10-4-6-11(16-2)7-5-10/h4-9H,3H2,1-2H3/b9-8+

Upstream product

• 617-35-6 2-oxo-propionic acid ethyl ester 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 924-44-7 glyoxylic acid ethyl ester 
• 17614-89-0 (2-(4-methoxyphenyl)-2-oxoethyl)triphenylphosphonium bromide 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 64-17-5 ethanol 
• 20972-37-6 (E)-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid 
• 87-91-2 diethyl (2R,3R)-tartrate 
• 1076-95-5 p-methoxyphenylglyoxal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 100-66-3 methoxybenzene 
• 5711-41-1 3-(4-methoxybenzoyl)acrylic acid 
• 108-31-6 maleic anhydride 

Downstream Products

• 1107060-57-0 1-(4-methoxybenzoyl)cyclopropane-2,3-dicarboxylic acid diethyl ester 
• 1185985-44-7 1-ethyl 4-(4-methoxyphenyl) (R)-2-(nitromethyl)succinate 
• 919513-66-9 ethyl (R)-5-oxopyrrolidine-3-carboxylate 
• 1185984-75-1 ethyl (R)-4-(4-methoxyphenyl)-2-(nitromethyl)-4-oxobutanoate 
• 5711-41-1 3-(4-methoxybenzoyl)acrylic acid 

Relevant articles and documents

An efficient synthesis of β-Aroylacrylic acid ethyl ester by the Friedel-Crafts reaction in the presence of diethyl sulfate

An β-Aroylacrylic acid ethyl ester such as ethyl (E)-4-(3,4- dimethoxyphenyl)-4-oxo-2-butenoate (1) can be obtained in good yield and with excellent purity by way of the Friedel-Crafts reaction in which 1,2-dimethoxybenzene (2) is treated with maleic anhydride (3) and aluminum chloride in the presence of diethyl sulfate (4) under mild conditions. Copyright

Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents

A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against MTB with MIC ranging from 0.125 to 4 μg/mL. Especially, compound IIIa16 was found to have the best activity with MIC of 0.125 μg/mL against MTB and with MIC in the range of 0.05–0.48 μg/mL against drug-resistant clinical MTB isolates.

Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study

Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the α,β-unsaturated ketone scaffold and “trans-” configuration are essential for the activity against PknB. And compounds with an aryl group, especially with electron-withdrawing substituents on benzene ring, exhibited four fold potency than that of YH-8.