1878-29-1

Usage

Uses

Used in Pharmaceutical Synthesis:
3,4,5-Trimethoxycinnamic acid ethyl ester is used as an intermediate in the synthesis of pharmaceuticals for its potential therapeutic properties. Its antioxidant, anti-inflammatory, and anti-tumor characteristics make it a valuable component in the development of new drugs targeting various health conditions.
Used in Flavor and Fragrance Industry:
In the flavor and fragrance industry, 3,4,5-Trimethoxycinnamic acid ethyl ester is used as a key ingredient to impart unique scents and tastes to various products. Its natural origin and distinctive properties contribute to the creation of innovative and appealing fragrances and flavor profiles.
Used in Antioxidant Applications:
3,4,5-Trimethoxycinnamic acid ethyl ester is utilized as an antioxidant in various applications, including food preservation and cosmetic formulations. Its ability to neutralize free radicals and protect against oxidative stress makes it a valuable additive for enhancing the shelf life and efficacy of products.
Used in Anti-inflammatory Formulations:
Due to its anti-inflammatory properties, 3,4,5-Trimethoxycinnamic acid ethyl ester is used in the development of anti-inflammatory agents. It can be incorporated into topical creams, ointments, or oral medications to help reduce inflammation and alleviate pain associated with various conditions.
Used in Antitumor Research:
3,4,5-Trimethoxycinnamic acid ethyl ester is employed in antitumor research as a potential agent for inhibiting tumor growth and progression. Its ability to target multiple signaling pathways involved in cancer development makes it a promising candidate for further investigation and potential use in cancer therapy.
Used in Antimicrobial Agents:
In the field of antimicrobial agents, 3,4,5-Trimethoxycinnamic acid ethyl ester is used for its potential to inhibit the growth of certain bacteria and fungi. This property can be harnessed in the development of new antibiotics, antifungal agents, or disinfectants to combat microbial infections.
Overall, 3,4,5-Trimethoxycinnamic acid ethyl ester is a multifaceted compound with diverse applications across various industries, including pharmaceuticals, flavor and fragrance, food and beverage, cosmetics, and antimicrobial agents. Its unique properties and potential health benefits make it a valuable asset in the development of innovative products and therapies.

InChI:InChI=1/C14H18O5/c1-5-19-13(15)7-6-10-8-11(16-2)14(18-4)12(9-10)17-3/h6-9H,5H2,1-4H3/b7-6+

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 64-17-5 ethanol 
• 141-82-2 malonic acid 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 140-88-5 ethyl acrylate 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 105-36-2 ethyl bromoacetate 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 4698-21-9 3-(3,4,5-trimethoxyphenyl)propiolic acid 
• 123251-29-6 3-methoxy-4,5-methylenedioxycinnamyl 3',4',5'-trimethoxyphenylpropiolate 
• 134302-94-6 3-ethyl 2-methyl rel-(2R,3S,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 
• 134310-05-7 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-3-piperonyloyl-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate 
• 75404-00-1 ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate 
• 112778-68-4 (6R,7S,8R)-5-Oxo-8-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid diethyl ester 
• 1253204-25-9 C₁₄H₂₀O₇ 
• 1415686-49-5 (E)-3-((4-chlorophenyl)(hydroxy)methyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one 
• 1415686-50-8 (E)-3-((4-fluorophenyl)(hydroxy)methyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one 
• 1415686-51-9 (E)-3-(hydroxy(2-nitrophenyl)methyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one 
• 1415686-52-0 (E)-3-(hydroxy(4-nitrophenyl)methyl)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one 
• 1415686-53-1 (E)-4-(hydroxy(2-oxo-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-1,2,5,6-tetrahydropyridin-3-yl)methyl)benzonitrile 
• 1703-35-1 (E)-1-(pyrrolidine-1-yl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one 
• 82017-78-5 1-[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]piperidin-2-one 

Relevant academic research and scientific papers

Synergistic Cooperative Effect of L-Arginine-[bmim]Br in Cascade Decarboxylative Knoevenagel-Thia-Michael Addition Reactions: Green Approach Towards C?S Bond Formation with In Situ Generated Unactivated α,β-Unsaturated Ester

In this report, a synergistic combination of L-arginine and [bmim]Br has been realized for the first time towards step-economical synthesis of β-aryl-β-sulfanyl esters from aromatic aldehyde, malonate and thiol via cascade thia-Michael addition reaction on in situ formed unactivated β-aryl-α,β-unsaturated esters (via decarboxylative Knoevenagel reaction) under metal-and acid/base-free conditions. Furthermore, the gram scalability and recyclability of the catalytic system (up to 5 cycles) makes our one-pot two-step protocol more economically efficient and synthetically attractive for cascade C?C and C?S bond formation than traditional two-step methods. The synergistic interaction of the catalytic system i. e. L-arginine with [bmim]Br has been probed by NMR (1H and 13C) studies. (Figure presented.).

Concise and efficient synthesis of cinepazide

An efficient synthesis of cinepazide has been carried out in four steps with an overall yield of 51%. The synthesis was started from a commercially available 3,4,5-tri-methoxy benzaldehyde. All the reactions were very clean and the isolation of products was also very easy.

First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity

The first synthesis of natural phenolic amides, tabamides A–C (1–3), and their derivatives (4–12) was accomplished using Stobbe condensation and amide coupling reactions as key steps. The in vitro nitric oxide (NO) inhibitory effects of these compounds in LPS-induced RAW-264.7 macrophages were evaluated as an indicator of anti-inflammatory activity. All compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without significant cytotoxicity. Compound 6, a tabamide A derivative (IC50 = 82.6 μM), followed by tabamide A (1, IC50 = 100.7 μM), was the most potent from the series. The present study revealed that tabamide A (1) could be considered as a lead structure to develop NO production-targeted anti-inflammatory agents.

Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues

With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.

Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents

We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.

Synthesis method of beta-chloro acid ester and alpha, beta-unsaturated acid ester compound

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of beta-chloro acid ester and an alpha, beta-unsaturated acid ester compound. The structure of the compound is characterized by 1H NMR and 13C NMR and is confirmed. The method comprises the steps of by taking acetonitrile as a solvent, carrying out fragmentation on olefin, chlorooxalic acid monoester and 2, 6-dimethyl pyridine under a photocatalytic condition to generate an alkoxyacyl free radical intermediate, carrying out free radical addition reaction on the alkoxyacyl free radical intermediate and the olefin to generate carbon free radicals, then carrying out chlorination reaction to obtain the beta-chloro acid ester compound, and carrying out dehydrochlorination reaction under a DBU condition to generate the alpha, beta-unsaturated acid ester compound. The preparation method of the compound disclosed by the invention has the advantages of starting from olefin, being mild in condition, simple and efficient, strong in functional group compatibility and wide in substrate application range, and various beta-chloro acid ester and alpha, beta-unsaturated acid ester compounds can be synthesized from highly commercialized raw materials. On the basis of photoreaction of fluid chemistry, a target product can also be obtained with a relatively good yield, and the method has very good industrial and medicinal chemistry application values.

Preparation method for cinepazide maleate

The invention provides a preparation method for cinepazide maleate, which comprises the following steps of: (1) carrying out Wittig reaction on 3, 4, 5-trimethoxybenzaldehyde serving as an initial rawmaterial and phosphine ylide to obtain (E)-3, 4, 5-trimethoxyethyl cinnamate (intermediate I), (2) hydrolyzing the (E)-3, 4, 5-trimethoxyethyl cinnamate to obtain a key intermediate 3, 4, 5-trimethoxy cinnamic acid (intermediate II), (3) in the presence of 1-hydroxybenzotriazole, triethylamine and carbodiimide hydrochloride, coupling the intermediate I with anhydrous piperazine to synthesize 1-(3, 4, 5-trimethoxycinnamoyl) piperazine (intermediate III), (4) reacting the 1-(3, 4, 5-trimethoxycinnamoyl) piperazine with 2-bromo-1 (pyrrolidine-1-yl) ethyl ketone to generate cinepazide (an intermediate IV), and (5) salifying the cinepazide in the step (4) and maleic acid to generate the target product cinepazide maleate. The preparation method has the advantages of cheap and easily available raw materials, simple operation, short production period, high yield, easy purification, good control of the product quality, reduction of the pollutant discharge, environmental protection, and realization of industrial production.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

Asymmetric total synthesis of dihydroisocoumarins: 6-methoxymellein, kigelin and fusarentin 6, 7 dimethyl ether by employing proline catalysed asymmetric α-aminoxylation

A concise asymmetric total synthesis of dihydroisocoumarins such as 6-methoxymellein, kigelin and fusarentin 6,7-dimethyl ether in high enantiopurity have been achieved from non-chiral aldehydes by employing proline catalysed asymmetric α-aminoxylation reaction. The required stereochemistry of hydroxyl group have been generated by alternating L or D proline as a organocatalyst in α-aminoxylation step and lactone ring is assembled by oxa-Pictet-Spengler cyclisation reaction as the key steps.

A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase

By constructing an in vivo-assembled, catalytically proficient peroxidase, C45, we have recently demonstrated the catalytic potential of simple, de novo-designed heme proteins. Here, we show that C45's enzymatic activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.