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Usage

Uses

Used in Pharmaceutical Industry:
3-[3,4-bis(acetoxy)phenyl]acrylic acid is utilized as a key intermediate in the synthesis of pharmaceutical compounds due to its ability to participate in a range of chemical reactions, facilitating the development of new drugs with potential therapeutic applications.
Used in Agricultural Industry:
In agriculture, 3-[3,4-bis(acetoxy)phenyl]acrylic acid serves as a chemical building block for the creation of agrochemicals, such as pesticides and herbicides, leveraging its reactivity to form molecules with specific biological activities aimed at crop protection.
Used in Material Science:
3-[3,4-bis(acetoxy)phenyl]acrylic acid is employed as a component in the development of advanced materials, including polymers and composites, due to its capacity to undergo various chemical modifications that can enhance material properties like strength, flexibility, or responsiveness to environmental stimuli.
Used in Organic Synthesis:
3-[3,4-bis(acetoxy)phenyl]acrylic acid is used as a versatile intermediate in organic synthesis for the preparation of a wide array of complex organic molecules, capitalizing on the reactivity of its acetoxy groups to form diverse chemical linkages and structures.

InChI:InChI=1/C13H12O6/c1-8(14)18-11-5-3-10(4-6-13(16)17)7-12(11)19-9(2)15/h3-7H,1-2H3,(H,16,17)/b6-4+

Upstream product

• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 331-39-5 caffeic acid 
• 331-39-5 cis-caffeic acid 
• 141-82-2 malonic acid 
• 67727-64-4 3,4-diacetoxybenzaldehyde 

Downstream Products

• 66417-50-3 (E)-methyl 3-(3,4-diacetoxyphenyl)acrylate 
• 57142-64-0 3,4-diacetoxystyrene 
• 331-39-5 caffeic acid 
• 64-19-7 acetic acid 
• 1224851-63-1 2-acetoxy-benzoic acid 2-[3-(3,4-di-acetoxy-phenyl)-acryloyloxy]-ethyl ester 
• 1073897-83-2 1,4,5-tri-O-caffeoylquinic acid 
• 14534-61-3 4,5-di-O-caffeoylquinic acid 
• 343326-56-7 C₂₆H₃₀O₁₁ 

Relevant academic research and scientific papers

Mechanism of high thermal stability of commercial polyesters and polyethers conjugated with bio-based caffeic acid

In previous report, we discovered that a novel improvement technique to enhance the thermal properties of poly(L-lactide)s (PLLAs) by terminal conjugation with 3,4-diacetoxycinnamic acid (DACA). In this study, we clarified the mechanism of the enhancement of thermal stability by using commercial polyesters and polyethers. The effect of thermal improvement by the terminal conjugation of DACA on poly(DL-lactide), poly(ε-caprolactone), and poly(ethylene glycol) was almost the same as about 100 °C increase. The amount of residual tin catalyst, which enhances the thermal degradation of polyesters, was reduced at undetected level after the terminal conjugation of DACA probably due to the removal of tin during DACA conjugation process. Furthermore, the π-π stacking interactions of DACA units and the chemical protection of terminal hydroxyl groups, which enhances intramolecular scission, were also important for the high thermal stability. We clarified that the extreme high thermal stability by DACA conjugation was induced by these above mechanisms.

A stereocomplex of poly(lactide)s with chain end modification: Simultaneous resistances to melting and thermal decomposition

The simultaneous improvement of the melting temperature (Tm = 224 °C) and the decomposition temperature (T10 = 359 °C) of poly(lactide)s was achieved by the stereocomplex formation of poly(l-lactide) and poly(d-lactide) with bio-based aromatic groups at both initiating and terminating chain ends.

Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents

Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PC12 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PC12 cells in a dose-dependent manner. The anti-apoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure-activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia.

Polymerization of the triphosphates of AraC, 2',2'-difluorodeoxycytidine (dFdC) and OSI-7836 (T-araC) by human DNA polymerase alpha and DNA primase.

OSI-7836 (4'-thio-araC, T-araC) is a nucleoside analogue that shows efficacy against solid tumor xenograft models. We examined how the triphosphates of OSI-7836 (T-araCTP), cytarabine (araCTP), and gemcitabine (dFdCTP) affected the initiation of new DNA strands by the pol alpha primase complex. Whereas dFdCTP very weakly inhibited primase, both T-araCTP and araCTP potently inhibited this enzyme. Primase polymerized T-araCTP and araCTP more readily than its natural substrate, CTP, and incorporation resulted in strong chain termination. dFdCTP, araCTP, and T-araCTP inhibited pol alpha competitively with respect to dCTP. When exogenously added primentemplates were used, pol alpha incorporated all three analogues into DNA, and incorporation caused either weak chain termination (dFdCTP), strong termination (araCTP), or extremely strong termination (T-araC). Furthermore, pol alpha polymerized T-araCTP only nine-fold less well than dCTP, whereas it polymerized araCTP and dFdCTP 24- and 83-fold less well, respectively. The presence of these three analogues in the template strand resulted in significant pausing by pol alpha, although the site and severity of pausing varied between the analogues. During the elongation of primase-synthesized primers, a reaction that is thought to mimic the normal sequence of events during the initiation of new DNA strands, pol alpha polymerized all three compounds. However, incorporation of araCTP and dFdCTP resulted in minimal chain termination, while incorporation of T-araCTP still caused extremely strong termination. The implications of these results with respect to how these compounds affect cells are discussed.

Thermally stable and photoreactive polylactides by the terminal conjugation of bio-based caffeic acid

Caffeic acid terminally conjugated with polylactide showed high thermal stability and photoreactivity, and may be useful as a functional polylactide in the environmental and medical fields. The Royal Society of Chemistry.

Synthesis of cinnamoyl ketoamides as hybrid structures of antioxidants and calpain inhibitors

The excessive calpain activation causes serious cellular damage or even cell death in neurological disorders such as stroke and Alzheimer's disease. Oxidative stress has also been implicated in the initiation or progression of neurodegenerative diseases. In the present studies, a series of cinnamoyl ketoamides 4a-4j were synthesized as hybrid structures of antioxidants and calpain inhibitors. Cinnamoyl ketoamides, possessing an alkyl chain at the α-position, showed potent μ-calpain inhibitory activities indicating that the cinnamoyl skeleton can be regarded as an acyclic variant of calpain inhibitory chromone carboxamide 2. Among synthesized, compound 4e was the most potent inhibitor of μ-calpain (IC50 = 0.13 μM) and also exhibited strong antioxidant activities in DPPH and superoxide anion radical scavenging and lipid peroxidation inhibition assay systems.

Synthesis of caffeic acid sulfonamide derivatives and their protective effect against H2O2 induced oxidative damage in A549 cells

Exogenous antioxidants are considered as important therapeutic tools for oxidative stress associated disorders as they can regulate the redox state, which is associated with cell and organ function. Inspired by natural polyphenols, six new caffeic acid sulfonamide derivatives were synthesized by coupling sulfonamides to the backbone of caffeic acid with good yields. Their structure and lipophilicity were characterized by 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, infrared spectroscopy (IR) and oil-water partition coefficient assay. Their free radical scavenging activity and antioxidant activity were assessed by DPPH assay and hydrogen peroxide (H2O2) induced oxidative stress in human lung carcinoma A549 cells. The oil-water partition coefficient results indicate that the conjugation of sulfonamides increases the lipophilicity of caffeic acid. The CASMD, CASDZ and CASN results show higher free radical scavenging effects compared with vitamin C. The derivatives do not show any inhibitory effect on the proliferation of A549 cells up to a concentration of 200 μM, except CASDZ which significantly inhibits the growth of A549 cells at a concentration of 200 μM. In addition, the obtained derivatives markedly attenuate H2O2 induced decrease of cell viability, inhibit the production of ROS and MDA, and promote the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px). Besides, treatment of H2O2 stimulated A549 cells with caffeic acid sulfonamide derivatives further increases mRNA expression of NF-E2-related factor 2 (Nrf2) and its target genes, including heme oxygenase-1 (HO-1), NAD(P)H quinone dehydrogenase 1 (NQO1) and thioredoxin reductase 1 (TXNRD1). These results suggest that these new caffeic acid sulfonamide derivatives have higher lipophilicity and better antioxidant activities than the parent caffeic acid, and they might be able to control the antioxidant response in cells via the Nrf2 pathway.

Novel 3C-like protease inhibitor as well as preparation method and application thereof

The invention provides a novel 3C-like protease inhibitor which is 3 ", 4" - O - diacetyl -epicatechin trans-caffeic acid ester with a specific structure. The invention further provides a preparation method and application of the 3C-like protease inhibitor. The invention has the advantages that the compound 3 ", 4" - O - diacetyl - epicatechin trans-caffeic acid ester is designed and synthesized based on the structure of epicatechin; even when the concentration is low, the activity of 3C-like protease in the novel coronavirus can be obviously inhibited. The compounds can be used as 3C-like protease inhibitors and are used for preparing anti-novel coronavirus SARS-CoV - 2 infection drugs.

ORAL PHARMACEUTICAL FORMULATIONS OF BITTER COMPOUNDS FOR PULMONARY HYPERTENSION

There is disclosed an oral pharmaceutical formulation of bitter compounds that are agonists of TAS2R receptors for the treatment of pulmonary hypertension (PAH). More specifically, there is disclosed a PAH oral formulation comprising a bitter agent selected from the group consisting of 3-caffeoylquinic-1,5-lactone (3-CQL), chlorogenic acid (CGA), denatonium benzoate (DB), denatonium chloride (DC), denatonium saccharide (DS), denatonium acetate (DA), and combinations thereof and a PDE-5 inhibitor.

1 - O - dicafeoyl quininic acid, its derivatives, preparation method and use thereof (by machine translation)

The invention of the formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives, and 1 - O - dicafeoyl quininic acid, of formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives and its application of salt. 1 - O - dicafeoyl quininic acid, of formula (II) as shown by a 1 - O - caffenoylquinate acid derivatives and the salts thereof inhibit interleukin 17, in particular interleukin 17 F of secretion, and capable of preventing and treating the tumor. Experimental results show that, 1 - O - dicafeoyl quininic acid concentration is 0.5 μm/L when the interleukin 17 F inhibition rate of close to 70%; 1 - O - dicafeoyl quininic acid in 20 mg/kg at a dose to the melanoma, pancreatic cancer, colorectal cancer, lung cancer tumor has good inhibition effect, are more than 50%, and its derivatives black pigment lump, pancreatic cancer, colorectal cancer, lung cancer tumor also has better inhibition effect. (by machine translation)