17812-07-6

Basic information

• Product Name: trans-3-Benzoylacrylic acid
• Synonyms: TRANS-3-BENZOYLACETICACID;4-PHENYL-4-OXOBUTYRIC ACID;(E)-3-Benzoylacrylic acid;(E)-3-Benzoylpropenoic acid;(E)-4-Phenyl-4-oxo-2-butenoic acid;(2E)-4-OXO-4-PHENYLBUT-2-ENOIC ACID;3-BENZOYLACRYLIC ACID;4-OXO-4-PHENYL-2-BUTENOIC ACID
• CAS NO: 17812-07-6
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• EINECS: 209-496-5
• Mol File: 17812-07-6.mol

Chemical Properties

• Melting Point: 94-97 °C(lit.)
• Appearance: /
• Density: 1.238
• CAS DataBase Reference: trans-3-Benzoylacrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-Benzoylacrylic acid(17812-07-6)
• EPA Substance Registry System: trans-3-Benzoylacrylic acid(17812-07-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: EM9259050
• Hazardous Substances Data: 17812-07-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-3-Benzoylacrylic acid is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
It serves as a key intermediate in the production of dyes and pigments, playing a crucial role in the creation of colorants for various applications.
Used in Research and Development:
Trans-3-Benzoylacrylic acid is utilized in research and development for exploring its potential medicinal properties, making it a significant chemical in the advancement of drug discovery and development processes.

Upstream product

• 108-31-6 maleic anhydride 
• 60-29-7 diethyl ether 
• 28557-00-8 phenylzinc chloride 
• 71-43-2 benzene 
• 19522-26-0 3-benzoyl-2-propenoic acid 
• 36680-28-1 (Z)-3-(ethoxycarbonyl)propenoyl chloride 
• 15121-89-8 ethyl (E)-4-oxo-4-phenyl-2-butenoate 
• 92865-13-9 3-Benzoyl-milchsaeure-butylester 
• 53366-80-6 4,4-diethoxy-1-phenylbut-2-yn-1-one 
• 77934-61-3 (-)-3-benzoyl-2-<(p-nitrophenyl)thio>propionic acid 
• 135578-09-5 2,2-dimethyl-5-phenacyl-5-chloro-1,3-dioxane-4,6-dione 
• 124658-40-8 2-(Dimethoxy-phosphoryl)-4-oxo-4-phenyl-butyric acid 
• 63104-90-5 α-bromo-β-benzoylpropionic acid 
• 135578-08-4 2,2-dimethyl-5-phenacyl-1,3-dioxane-4,6-dione 

Downstream Products

• 101090-36-2 2-(5-methyl-pyrrol-2-yl)-4-oxo-4-phenyl-butyric acid 
• 103503-90-8 1-methyl-2,5-bis-(3-oxo-3-phenyl-propyl)-pyrrole 
• 14274-07-8 methyl trans-β-benzoylacrylate 
• 102664-64-2 4,4'-dioxo-4,4'-diphenyl-2,2'-pyrrole-2,5-diyl-di-butyric acid 
• 4370-96-1 4-oxo-2,4-diphenylbutanoic acid 
• 15121-89-8 ethyl (E)-4-oxo-4-phenyl-2-butenoate 
• 100886-24-6 4-methyl-5-oxo-3-phenyl-cyclohex-3-enecarboxylic acid 
• 102664-97-1 (+/-)-trans-12-benzoyl-9,10-dihydro-9,10-ethano-anthracene-carboxylic acid-⁽¹¹⁾ 
• 101423-14-7 6-chloro-2-phenacyl-4H-benzo[1,4]thiazin-3-one 
• 19522-26-0 3-benzoyl-2-propenoic acid 
• 99389-54-5 4-hydroxy-4-phenylbut-2-enoic acid 
• 122456-91-1 4-oxo-4-phenyl-trans-crotonic acid-anhydride 
• 117793-93-8 3-chloro-4-oxo-4-phenyl-crotonic acid 
• 4437-14-3 (E)-5,5'-diphenyl-3,3'-bifuranylidene-2,2'-dione 

Relevant articles and documents

Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans

A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been established via the [4 + 1] annulation of enaminones and BrCF2CO2Et with Na2CO3 promotion. This new protocol does not employ any transition metal reagent and enables the annulative difluoromethylation by the partial cleavage of the C═C double bond. In addition, the further treatment with hydrochloric acid in one pot leads to β-keto enoic acids (4-oxo-2-butenoic acids) via a formal enaminone C-N carboxylation.

Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives

The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino tra

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR

In this study, a series of shikonin derivatives combined with benzoylacrylic had been designed and synthesized, which showed an inhibitory effect on both tubulin and the epidermal growth factor receptor (EGFR). In vitro EGFR and cell growth inhibition assay demonstrated that compound PMMB-317 exhibited the most potent anti-EGFR (IC50 = 22.7 nM) and anti-proliferation activity (IC50 = 4.37 μM) against A549 cell line, which was comparable to that of Afatinib (EGFR, IC50 = 15.4 nM; A549, IC50 = 6.32 μM). Our results on mechanism research suggested that, PMMB-317 could induce the apoptosis of A549 cells in a dose- and time-dependent manner, along with decrease in mitochondrial membrane potential (MMP), production of ROS and alterations in apoptosis-related protein levels. Also, PMMB-317 could arrest cell cycle at G2/M phase to induce cell apoptosis, and inhibit the EGFR activity through blocking the signal transduction downstream of the mitogen-activated protein MAPK pathway and the anti-apoptotic kinase AKT pathway; typically, such results were comparable to those of afatinib. In addition, PMMB-317 could suppress A549 cell migration through the Wnt/β-catenin signaling pathway in a dose-dependent manner. Additionally, molecular docking simulation revealed that, PMMB-317 could simultaneously combine with EGFR protein (5HG8) and tubulin (1SA0) through various forces. Moreover, 3D-QSAR study was also carried out, which could optimize our compound through the structure-activity relationship analysis. Furthermore, the in vitro and in vivo results had collectively confirmed that PMMB-317 might serve as a promising lead compound to further develop the potential therapeutic anticancer agents.

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.

Application of 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents

The invention discloses application of a 4-oxo-2-crotonamide derivative to preparation of bacteriostatic agents. The structure of the 4-oxo-2-crotonamide derivative is shown as a formula (I). The 4-oxo-2-crotonamide derivative has a bacteriostatic effect; good antibacterial activity can be realized on methicillin-resistant staphylococcus aureus, methicillin-resistant staphylococcus epidermidis, vancomycin drug-resistant enterococcus faecalis, vancomycin drug-resistant enterococcus faecium, methicillin-sensitive staphylococcus aureus, methicillin-sensitive staphylococcus epidermidis, vancomycin-sensitive enterococcus faecalis and vancomycin-sensitive enterococcus faecium. The formula I is shown in the description.

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.

Iodine-Catalyzed Oxidative Aromatization: A Metal-Free Concise Approach to meta-Substituted Phenols from Cyclohex-2-enones

A metal-free approach to meta-substituted phenols from cyclohex-2-enone via catalytic oxidative aromatization has been developed. The transformations are initiated with a catalytic amount of molecular iodine as the direct oxidant, while dimethyl sulfoxide is employed as the terminal oxidant. This practical approach is capable of avoiding the use of metal promoters and costly reagents, the lengthy synthesis, and overoxidation of products, and thus facilitates the efficient construction of meta-substituted phenol derivatives from inexpensive commercial chemicals under mild conditions. The synthetic utility of this approach is evident in the de novo syntheses of two bioactive molecules with good total yields, in which easily available chemicals were employed, protective groups were not utilized, and no unwanted carbon atoms were removed in each step. (Figure presented.).

Hydrogen-bond-directed formal [5 + 1] annulations of oxindoles with ester-linked bisenones: Facile access to chiral spirooxindole δ-lactones

A novel bifunctional thiourea catalyzed formal [5 + 1] cycloaddition of oxindoles and ester-linked bisenones was successfully developed. This strategy involves two sequential Michael additions, leading to spirooxindole δ-lactones with three contiguous ste

(E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization

Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations.