16837-14-2

Usage

Uses

Used in Organic Synthesis:
2,2,5-Trimethyl-1,3-dioxane-5-carboxylic Acid is used as a synthetic building block for the development of new organic compounds. Its versatile structure allows for a wide range of applications in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2,5-Trimethyl-1,3-dioxane-5-carboxylic Acid is used as an intermediate in the synthesis of various drugs. Its unique chemical properties enable the creation of complex molecular structures that can target specific biological pathways, potentially leading to the development of novel therapeutic agents.
Used in Agrochemical Industry:
2,2,5-Trimethyl-1,3-dioxane-5-carboxylic Acid is also employed in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its incorporation into these compounds can enhance their effectiveness and selectivity, contributing to more sustainable and efficient agricultural practices.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2,2,5-Trimethyl-1,3-dioxane-5-carboxylic Acid is used as a key component in the development of advanced materials with specific properties. These materials can be tailored for various applications, such as in the electronics, coatings, and adhesives industries, where their unique characteristics can provide significant advantages.

InChI:InChI=1/C8H14O4/c1-7(2)11-4-8(3,5-12-7)6(9)10/h4-5H2,1-3H3,(H,9,10)

Upstream product

• 4767-03-7 2,2-bis(hydroxymethyl)propionic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 1910-47-0 3-hydroxyisobutyric acid 

Downstream Products

• 162635-10-1 2,4,6-trichlorobenzoic-2',2',5'-trimethyl-1',3'-dioxane-5'-carboxylic anhydride 
• 331810-11-8 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid chloride 
• 162635-03-2 rapamycin 42-ester with 2,2,5-trimethyl[1,3]dioxane-5-carboxylic acid 
• 428820-33-1 C₄₄H₅₄O₁₂ 
• 1439390-99-4 C₂₁H₂₅FN₆O₄S₂ 
• 1439400-04-0 N-(5-(4-(5-(2-(3-fluorophenyl)acetamido)-1,3,4-thiadiazol-2-yl)butyl)-1,3,4-thiadiazol-2-yl)-2,2,5-trimethyl-1,3-dioxane-5-carboxamide 
• 873849-86-6 (OH)2-[G-1]-Az 
• 919988-18-4 (HO)4-[G₂]-N₃ 
• 873849-89-9 C₄₁H₆₉N₃O₂₂ 

Relevant academic research and scientific papers

New formulation of old aspirin for better delivery

For better use of cyclooxygenase dependent anti-inflammatory properties and mitochondrial activities of aspirin, new hydrophobic analogues of aspirin were developed and successfully encapsulated in polymeric nanoparticles (NPs). In vivo anti-inflammatory effects of these NPs using a mouse model demonstrated unique properties of an optimized aspirin analogue to inhibit production of pro-inflammatory and enrichment of anti-inflammatory cytokines.

Heterogeneous Rupturing Dendrimers

Utilizing macromolecular scaffolds as templates for the production of small molecules that are distinctively different from the original monomer feedstock has many potential applications. Herein, as a proof-of-concept, a family of dendrimers displaying internally queued disulfide bridges were synthesized and exploited as flawless macromolecular templates that selectively rupture into a set of monomeric mercaptans. Disassembly was accomplished in a reducing environment, using DTT as an external stimulus, and the thiol constituents were successfully isolated. Their composition was dictated by three dendritic regions, i.e., (i) the symmetrical trithiol of the core (C3), (ii) the interior-asymmetric trithiols (CD2), and (iii) the periphery-asymmetric monothiols (DB2), in which B functionality is of an orthogonal nature. Taking into account the steady state between disulfides and thiols in all living cells, the collapse of the dendrimers to a multitude of smaller thiols was intracellularly assessed as a means to disrupt the balance of reactive oxygen species (ROS) often elevated in cancer cells. Indeed, the fragmentation induced a significant increase of ROS in human lung carcinoma A549 cells. These findings can potentially alter the perception of dendrimers being limited to carriers to being prodrugs for intracellular delivery of ROS with the potential to fight cancer.

Oriented nanoporous lamellar organosilicates templated from topologically unsymmetrical dendritic-linear block copolymers

Dendrimers between the sheets: Environmentally responsive dendritic-linear block copolymers, based on poly(ethylene oxide) and a dendron derived from 2,2′-bis(hydroxymethyl)propionic acid (see structure), were used to organize organosilicate vitrificates into nanostructured lamellar morphologies. Upon thermolysis of the template, a perforated porous lamellar structure (4 nm) between organosilicate sheets (6-9 nm) was obtained. (Chemical Equation Presented).

Self-assembled micelles of well-defined pentaerythritol-centered amphiphilic A4B8 star-block copolymers based on PCL and PEG for hydrophobic drug delivery

Biodegradable star-shaped poly(ε-caprolactone) (PCL) with four arms were synthesized by ring-opening polymerization (ROP) from a symmetric pentaerythritol core via the ''core-first'' strategy. Subsequently, two samples of the amphiphilic A4B8 star-block copolymers with symmetrical topologies [4s(PCL-b-2sPEG)] were synthesized by a macromolecular coupling reaction between carboxyl-terminated poly(ethylene glycol) (PEG) and 4-arm star-shaped PCL macromers with eight -OH end groups. The latter was prepared by attaching 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid (HHMPA) to 4sPCL using a simple two-step reaction sequence. The in vitro cytotoxicity test indicated no apparent cytotoxicity. The amphiphilic star-block copolymers are capable of self-assembling into spherical micelles in water at room temperature, and they possess low critical micelle concentrations (CMCs) of 2～8 mg/L in aqueous solution which was determined by fluorescence spectroscopy using pyrene as a probe. Transmission electron microscopy (TEM) measurement demonstrated that the micelles exhibit a spherical shape with a size range of 30～50 nm in diameter. In addition, the hydrophobic and anticancer drug, quercetin, is loaded effectively in the polymeric micelles, suggesting that these new materials are appropriate candidates as hydrophobic drug nanocarriers.

Synthesis, Micellization, and Surface Activity of Novel Linear-Dendritic Carboxylate Surfactants

Two generations of novel linear-dendritic carboxylate surfactants C18-G1-(COONa)2 and C18-G2-(COONa)4 have been synthesized by the divergent method and their structures are characterized by 1H Nuclear Magnetic Resonance and Infrared analysis. The electrical conductivity measurement is used to measure the Krafft temperatures of C18-G1-(COONa)2 and C18-G2-(COONa)4, which are much smaller than those of the corresponding conventional surfactant sodium stearate. The markedly enhanced solubility of two linear-dendritic surfactants is ascribed to the high hydrophilicity of surfactant headgroups induced by the carboxylate and ester groups. The critical micelle concentration (CMC) values obtained from both the electrical conductivity and surface tension measurements indicate that the micellizations of linear-dendritic surfactants become favorable with the increase in the number of the surfactant headgroup. However, the surface activity parameters including the surface tension at the CMC, maximum surface excess, and minimum surface area reveal that C18-G1-(COONa)2 exhibits greater efficiency in absorbing at the air/water interface compared to C18-G2-(COONa)4, owing to their different steric repulsions of the surfactant headgroups. In addition, C18-G1-(COONa)2 and C18-G2-(COONa)4 have higher emulsifying ability than the conventional surfactants sodium stearate and sodium octadecyl sulfate.

Evaluation of thermal and oxidative stability of three generations of phenolic based novel dendritic fuel and lubricant additives

Antioxidants, particularly those designed for use in hydrocarbon media, suffer from a variety of limitations including high volatility and poor solubility. Using 2,2-bis(hydroxymethyl)propionic acid as the branching unit, a series of novel dendrons featuring 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic ester chain ends have been synthesised to provide improved solubility of such hindered phenolic antioxidants. The thermal stability, assessed by thermogravimetric analysis, revealed that all the functionalised dendrons have enhanced thermal stability when compared to commercial antioxidants (BHT, Irganox L135 and Irganox L57). Antioxidant ability was evaluated using pressurised differential scanning calorimetry and when blended with a lubricant base oil, at 0.5% w/w, an increase in antioxidant performance was observed when compared to the commercial antioxidants.

Catalytically active hybrid polyurethane with tetraaniline pendant groups: Synthesis, properties and self assembly

For the first time we report a novel hybrid polyurethane synthesized from tetraaniline-diol (TAni-(OH)2) and hexamethylene diisocyanate (HMDI) with pendant tetraaniline units on the back bone. The striking property of this unprecedented polyurethane is its electrochemical sensing of ascorbic acid and self assembly into core-shell type microstructures (microcapsules) in presence of aqueous acetic acid/n-octane interface. These microcapsules exhibited a wide range of pH responses in their absorption spectrum. The synthesized polyurethane containing pendant tetraaniline units showed good surface conductivity to the tune of 3.4 × 10-4 S/cm. The electrochemical investigation showed two single electron oxidations and two single electron reductions reversibly. We also investigated electrochemical sensing details of carbon paste electrode (CPE) fabricated with conducting polyurethane (TANI-PU) as ascorbic acid sensor (vitamin C, AA) in 0.2 M and pH 7 phosphate buffer solution. The fabricated electrode is useful in sensing as low as 1 mM of ascorbic acid. Self-assembly property was probed by optical and TEM studies which established the core-shell structure of the assembled species. The self assembled microcapsules exhibited pH dependent doping and dedoping processes as established by UV-Vis study.

Iodine-Containing Mass-Defect-Tuned Dendrimers for Use as Internal Mass Spectrometry Calibrants

Calibrants based on synthetic dendrimers have been recently proposed as a versatile alternative to peptides and proteins for both MALDI and ESI mass spectrometry calibration. Because of their modular synthetic platform, dendrimer calibrants are particular

Molecular brushes with extreme grafted side chain densities

A series of densely grafted poly(n-butyl acrylate) (PBA) molecular brushes with four different grafting densities were synthesized by the "grafting-from" approach using atom transfer radical polymerization (ATRP). A novel monomer, isopropylidene-2,2-Bis(methoxy)propionic hydroxyethylmethacrylate (IMPHMA), was synthesized and copolymerized with methyl methacrylate (MMA) under different monomer feed ratios to yield a series of linear poly(methyl methacrylate-stat-IMAPA), [PMMA-s-(PIMPHMA)]. The resulting copolymers were deprotected and transformed to macroinitiators, [PMMA-s-(PHEMA-IMPHMA-Br)]. n-Butyl acrylate (BA) was grafted from these macroinitiators to yield a series of molecular brushes, [PMMA-s-{(PIMPHMA)-g- PBA}], with various side chain lengths. Molecular brushes were characterized by gel permeation chromatography (GPC) and 1H NMR. PBA side chains were cleaved by acid hydrolysis, and the resulting linear PBA polymers were characterized by GPC to study initiation efficiency during the synthesis of molecular brushes. The initiation efficiency increased with polymerization time and decreased with macroinitiators that had more initiation sites. Atomic force microscopy (AFM) measurements demonstrated the characteristic molecular structure by resolving individual brush molecules.

Development of l-Amino-Acid-Based Hydroxyl Functionalized Biodegradable Amphiphilic Polyesters and Their Drug Delivery Capabilities to Cancer Cells

Hydroxyl-functionalized amphiphilic polyesters based on l-amino acid bioresources were designed and developed, and their nanoassemblies were explored as intracellular enzyme-biodegradable scaffolds for delivering anticancer drugs and fluorophores to cancer cells. To accomplish this task, acetal-masked multifunctional dicarboxylic ester monomer from l-aspartic acid was tailor-made, and it was subjected to solvent-free melt transesterification polycondensation with commercial diols to produce acetal-functionalized polyesters. Acid-catalyzed postpolymerization deprotection of these acetal-polyesters produced amphiphilic hydroxyl-functionalized polyesters. The amphiphilic polyesters were self-assembled in aqueous medium to produce nanoparticles of size 200 nm. Wide ranges of both water-soluble and water-insoluble anticancer drugs such as doxorubicin (DOX), camptothecin (CPT), and curcumin (CUR) and fluorophores such as Nile red (NR), Rose Bengal (RB), and Congo red (CR) were encapsulated in hydroxyl polyesters nanoparticles. In vitro drug release studies revealed that the aliphatic polyester backbone underwent lysosomal enzymatic-biodegradation to release the loaded cargoes at the intracellular compartments. Lysotracker-assisted live-cell confocal microscopy studies further confirmed the colocalization of the polymer nanoscaffolds in the lysosomes and supported their enzymatic-biodegradation for drug delivery. In vitro cytotoxicity studies showed that the nascent polymers were not toxic, whereas their anticancer drug-loaded nanoparticles exhibited excellent cell killing in cervical cancer (HeLa) cell lines. The drug-loaded (CPT, CUR, and DOX) and the fluorophore-loaded (NR, RB, and CR) polymer nanoparticles were highly luminescent; thus, the encapsulated polymer nanoparticles enabled the multiple color-tunable bioimaging in cancer cells in the entire visible region from blue to deep red. Time-dependent live-cell confocal microscopy studies established that the cellular uptake of drugs and fluorophores was 5 to 10-fold higher while they were delivered from the hydroxyl polyester platform. The hydroxyl polyester nanocarrier design strategy opens up new opportunities in drug delivery to cancer cells from a biodegradable polymer platform based on l-amino acids.