15486-19-8

Usage

General Description

4-ACETOXYCINNAMIC ACID, also known as p-acetoxyphenylacetic acid, is an organic compound with the chemical formula C11H10O4. It is a derivative of cinnamic acid and is commonly used in the synthesis of pharmaceuticals and as a flavoring agent. 4-ACETOXYCINNAMIC ACID has been studied for its potential antioxidant and anti-inflammatory properties, making it a subject of interest in the research and development of new drugs. In addition, it is also used in the production of fragrances and as a precursor for the synthesis of other organic compounds. Overall, 4-ACETOXYCINNAMIC ACID has various applications in the pharmaceutical, flavor, and fragrance industries due to its chemical properties and potential therapeutic benefits.

InChI:InChI=1/C11H10O4/c1-8(12)15-10-5-2-9(3-6-10)4-7-11(13)14/h2-7H,1H3,(H,13,14)/b7-4+

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 463-51-4 Ketene 
• 67-64-1 acetone 
• 7400-08-0 para-coumaric acid 
• 64-19-7 acetic acid 
• 878-00-2 4-formylphenyl acetate 
• 141-82-2 malonic acid 
• 7400-08-0 p-Coumaric Acid 
• 7361-92-4 ethyl 3-(4-hydroxyphenyl)prop-2-enoate 

Downstream Products

• 53901-95-4 p-acetoxycinnamoyl chloride 
• 869708-38-3 2-acetoxy-benzoic acid 2-[3-(4-acetoxy-phenyl)-acryloyloxy]-ethyl ester 
• 1202495-53-1 1-hydroxy-3-(4-acetoxyphenyl)-2-propen 
• 7400-08-0 para-coumaric acid 
• 1451377-32-4 C₁₃H₁₃NO₃ 
• 1358938-43-8 C₂₅H₃₀N₂O₄ 
• 1358938-41-6 C₃₃H₄₂N₂O₆ 
• 1358938-40-5 C₃₂H₄₀N₂O₆ 
• 1358938-39-2 C₃₁H₃₈N₂O₆ 
• 1358938-38-1 C₃₀H₃₆N₂O₆ 
• 1358938-37-0 C₂₉H₃₄N₂O₆ 
• 1358938-36-9 C₂₈H₃₂N₂O₆ 
• 1358938-47-2 C₂₉H₃₈N₂O₄ 
• 1358938-46-1 C₂₈H₃₆N₂O₄ 

Relevant academic research and scientific papers

P-coumaroyl malate derivatives of the Pandanus amaryllifolius leaf and their isomerization

A novel p-coumaroyl dimethyl malate (1) was isolated from the Pandanus amaryllifolius leaf in addition to three known analogs of p-coumaroyl dimethyl malate (2-4), and their structures were elucidated by analysis of the spectroscopic data. The p-coumaroyl malate derivatives were isolated as a mixture of E and Z isomers. To determine the cause of isomerization, the p-coumaroyl malate isolated in this study was synthesized. We concluded that the Z isomer might be an artifact generated from the E isomer through purification steps.

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation

During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.

Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids

A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.

P-coumaroyl malate derivatives of the Pandanus amaryllifolius leaf and their isomerization

A novel p-coumaroyl dimethyl malate (1) was isolated from the Pandanus amaryllifolius leaf in addition to three known analogs of p-coumaroyl dimethyl malate (2-4), and their structures were elucidated by analysis of the spectroscopic data. The p-coumaroyl malate derivatives were isolated as a mixture of E and Z isomers. To determine the cause of isomerization, the p-coumaroyl malate isolated in this study was synthesized. We concluded that the Z isomer might be an artifact generated from the E isomer through purification steps.

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.

METHOD OF PRODUCING BENZOIC ACID

PROBLEM TO BE SOLVED: To provide a novel synthesis method in the production of a benzoic acid and an industrially suitable production method using main materials derived from nonfossil resources. SOLUTION: This invention provides a method of producing a benzoic acid represented by formula (II), comprising the step of the ozonation of a compound represented by formula (I). COPYRIGHT: (C)2015,JPOandINPIT

Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases

The present study reports the synthesis of cinnamide derivatives and their biological activity as inhibitors of both cholinesterases and anticancer agents. Controlled inhibition of brain acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) may slow neurodegeneration in Alzheimer's diseases (AD). The anticholinesterase activity of phenylcinnamide derivatives was determined against Electric Eel acetylcholinesterase (EeAChE) and horse serum butyrylcholinesterase (hBChE) and some of the compounds appeared as moderately potent inhibitors of EeAChE and hBChE. The compound 3-(2-(Benzyloxy)phenyl)-N- (3,4,5-trimethoxyphenyl)acrylamide (3i) showed maximum activity against EeAChE with an IC50 0.29 ± 0.21 μM whereas 3-(2-chloro-6- nitrophenyl)-N-(3,4,5-trimethoxyphenyl)acrylamide (3k) was proved to be the most potent inhibitor of hBChE having IC50 1.18 ± 1.31 μM. To better understand the enzyme-inhibitor interaction of the most active compounds toward cholinesterases, molecular modelling studies were carried out on high-resolution crystallographic structures. The anticancer effects of synthesized compounds were also evaluated against cancer cell line (lung carcinoma). The compounds may be useful leads for the design of a new class of anticancer drugs for the treatment of cancer and cholinesterase inhibitors for Alzheimer's disease (AD).