13788-48-2

Basic information

• Product Name: 3-[3,4-bis(acetoxy)phenyl]acrylic acid
• Synonyms: 3-[3,4-bis(acetoxy)phenyl]acrylic acid;3-[3,4-Bis(acetyloxy)phenyl]propenoic acid;O,O'-Diacetylcaffeic acid
• CAS NO: 13788-48-2
• Molecular Formula: C₁₃H₁₂O₆
• Molecular Weight: 264.23078
• EINECS: 237-446-2
• Mol File: 13788-48-2.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 444.5°Cat760mmHg
• Flash Point: 169.6°C
• Appearance: /
• Density: 1.319g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: 3-[3,4-bis(acetoxy)phenyl]acrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[3,4-bis(acetoxy)phenyl]acrylic acid(13788-48-2)
• EPA Substance Registry System: 3-[3,4-bis(acetoxy)phenyl]acrylic acid(13788-48-2)

Safety Data

• Hazardous Substances Data: 13788-48-2(Hazardous Substances Data)

Usage

Description

3-[3,4-bis(acetoxy)phenyl]acrylic acid is a chemical compound characterized by the molecular formula C15H14O6. It is an acrylic acid derivative featuring two acetoxy groups at the 3 and 4 positions of a phenyl ring. 3-[3,4-bis(acetoxy)phenyl]acrylic acid is recognized for its role in organic synthesis and as a fundamental building block for constructing more elaborate molecular structures. Its versatility in chemical reactions, stemming from the presence of the acetoxy groups, positions 3-[3,4-bis(acetoxy)phenyl]acrylic acid as a valuable intermediate in various chemical syntheses. Moreover, it holds potential for applications across different industries, including pharmaceuticals, agriculture, and material science, with possible biological activities that warrant further exploration.

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 cis-caffeic acid 
• 331-39-5 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 
• 849589-35-1 C₁₇H₁₅NO₈ 
• 1156495-06-5 C₂₈H₂₅NO₁₀ 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 331-39-5 caffeic acid 
• 64-19-7 acetic acid 
• 57142-64-0 3,4-diacetoxystyrene 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 100884-13-7 caffeic acid 3-methyl-2-butenyl ester 

Relevant articles and documents

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.

PHYTOCHEMICAL STUDY OF Beonica officinalis. II. ACIDS FROM THE EPIGEAL PART OF Betonica

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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.

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 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.

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.

Design, synthesis, and biological evaluation of novel tetramethylpyrazine derivatives as potential neuroprotective agents

Oxidative stress plays a crucial role in neurological diseases, resulting in excessive production of reactive oxygen species, mitochondrial dysfunction and cell death. In this work, we designed and synthesized a series of tetramethylpyrazine (TMP) derivatives and investigated their abilities for scavenging free radicals and preventing against oxidative stress-induced neuronal damage in vitro. Among them, compound 22a, consisted of TMP, caffeic acid and a nitrone group, showed potent radical-scavenging activity. Compound 22a had broad neuroprotective effects, including rescuing iodoacetic acid-induced neuronal loss, preventing from tert-butylhydroperoxide (t-BHP)-induced neuronal injury. Compound 22a exerted its neuroprotective effect against t-BHP injury via activation of the phosphatidyl inositol 3-kinase (PI3K)/Akt signaling pathway. Furthermore, in a rat model of permanent middle cerebral artery occlusion, compound 22a significantly improved neurological deficits, and alleviated the infarct area and brain edema. In conclusion, our results suggest that compound 22a could be a potential neuroprotective agent for the treatment of neurological disease, particularly ischemic stroke.