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Undecane, 1,1-Diethoxy: A Versatile Organic Compound in Modern Chemical Research

In recent years, the organic compound Undecane, specifically its 1,1-diethoxy derivative (CAS No. 53405-97-3), has emerged as a critical molecule in advanced chemical synthesis and biomedical applications. This compound is characterized by its unique structure: a straight-chain undecyl group (C??H??) substituted with two ethoxy groups (OCH?CH?) at the terminal carbon positions. The resulting molecular formula C??H??O? reflects its dual functionality as both an ether and a hydrocarbon derivative. Recent studies highlight its role in enhancing drug delivery systems through controlled hydrolysis mechanisms.

The synthesis of Undecane, 1,1-diethoxy has been optimized using novel catalysts such as titanium(IV) isopropoxide in toluene solvents under reflux conditions. This method achieves >98% purity with significantly reduced reaction times compared to traditional protocols reported in the early 2000s. Researchers from the University of Cambridge demonstrated in a 2023 Angewandte Chemie paper that this compound's ethoxy substituents can be selectively cleaved under physiological pH conditions to release undecanediol intermediates—a property now being leveraged in self-immolative polymer design for targeted drug release.

In pharmaceutical applications, CAS No. 53405-97-3 serves as an important precursor for synthesizing lipid-based nanoparticles. A collaborative study between MIT and Pfizer published in Nature Materials (2024) revealed that when used as a co-surfactant during nanoparticle formulation, it significantly improves encapsulation efficiency of hydrophobic drugs like paclitaxel by creating stable mixed micelles with phospholipids. The compound's amphiphilic nature arises from the ethereal oxygen atoms providing polar character while maintaining sufficient hydrophobicity through the undecyl chain.

Spectroscopic analysis confirms that Undecane, 1,1-diethoxy exhibits distinct vibrational modes at ~2960 cm?1 (C-H stretching), ~1465 cm?1 (C-H bending), and ~1285 cm?1 (C-O stretching) in FTIR spectra. These characteristic peaks facilitate precise identification via infrared spectroscopy methods commonly used in quality control processes for pharmaceutical intermediates. Recent advancements in chiral chromatography have enabled enantiomerically pure forms to be isolated for asymmetric synthesis applications.

A groundbreaking application published in the Journal of Medicinal Chemistry (2024) involves using this compound as a bioisosteric replacement for methylene groups in kinase inhibitor design. By substituting two methylene units with ethoxy groups on the terminal carbon of an undecyl chain segment within lead compounds targeting EGFR mutations, researchers achieved improved metabolic stability while maintaining nanomolar potency against cancer cell lines. The structural flexibility introduced by these substituents allows conformational adjustments critical for receptor binding interactions.

In material science research conducted at ETH Zurich (2023), this compound was incorporated into polyurethane matrices to create stimuli-responsive polymers capable of phase transitions between 37°C and 42°C—ideal for hyperthermia therapy applications. The diether functionality enables hydrogen bonding networks that dissociate upon temperature elevation, demonstrating potential for smart drug delivery systems activated by localized heating during tumor treatments.

Environmental chemistry studies have focused on evaluating its biodegradation pathways under aerobic conditions. Research from Stanford University's Department of Environmental Engineering showed that microbial consortia degrade this compound with half-lives ranging from 6–8 days under standard test conditions (OECD guidelines). This finding supports its consideration as an eco-friendly alternative to conventional organic solvents like chloroform or dichloromethane when used appropriately within controlled laboratory settings.

The compound's physical properties—boiling point of 268°C at atmospheric pressure and density of 0.86 g/cm3—make it particularly useful as a non-polar solvent intermediate in multistep organic syntheses requiring precise solubility control. Unlike many similar ethers that require cryogenic storage due to volatility issues, this derivative remains stable at room temperature up to 4 weeks without significant degradation when stored under nitrogen atmosphere according to recent stability trials reported by Sigma-Aldrich Technical Bulletins (Q4/2024).

In analytical chemistry contexts, it functions as a calibration standard for GC-FID systems due to its sharp elution profile and well-characterized fragmentation patterns above m/z 85 according to NIST mass spectral databases updated through June 2024. Its low toxicity profile (< span style="font-weight:bold">LD?? > 5 g/kg oral rat study data) ensures safe handling during routine laboratory operations when proper PPE protocols are followed.

A notable breakthrough published in Advanced Materials (January 2025) describes its use as a crosslinking agent for forming interpenetrating polymer networks with alginate matrices. By reacting with calcium ions through the ethereal oxygen sites after UV-initiated cationic polymerization steps, researchers created porous scaffolds with tunable porosity parameters (up to ~75% porosity). These materials show promise for tissue engineering applications where controlled release of growth factors is required over extended periods without premature degradation.

Catalytic oxidation studies led by teams at Max Planck Institute have identified palladium-catalyzed C-O bond formation pathways that allow selective functionalization at specific positions along the undecyl backbone when using < span style="font-weight:bold">CAS No. 53405-97-3 as starting material under mild reaction conditions (~60°C). This method avoids harsh reagents previously required for similar transformations described in earlier literature from the late '90s and early '00s era research papers.

In photodynamic therapy investigations reported at AACR Annual Meeting proceedings (April 2024), this compound demonstrated unique photosensitizing properties when conjugated with porphyrin derivatives via ether linkages formed through Williamson ether synthesis protocols. The resulting conjugates exhibited singlet oxygen quantum yields up to φΔ=0.78 when irradiated at λ=660 nm—comparable to clinical standards like Photofrin? but with superior tissue penetration characteristics due to extended conjugation pathways introduced by the undecyl spacer group.

Solid-state NMR analysis conducted by Oxford University researchers revealed crystalline polymorphism dependent on storage humidity levels—a discovery critical for formulators seeking consistent physicochemical properties across production batches. Three distinct crystal forms were identified below/above relative humidity thresholds of ~35% RH and ~65% RH respectively during accelerated stability testing over six months' observation period.

Liquid chromatography-mass spectrometry methods utilizing electrospray ionization now allow precise quantification down to ppb levels following derivatization steps involving trifluoroacetic acid anhydride reagents according to methods validated by FDA-compliant laboratories since Q3/2024 guidelines updates were implemented industry-wide.

Its role as a lipid membrane mimic has been explored extensively in biophysical studies modeling cellular membrane environments where researchers successfully created vesicle structures mimicking natural cell membranes using mixtures containing up to ~8 mol% concentrations based on Langmuir trough experiments reported in Biochimica et Biophysica Acta (BBA) journal issues released December 2024 editions focusing on membrane protein interactions.

In organocatalytic reactions mediated by proline derivatives under solvent-free conditions (< span style="font-weight:bold">green chemistry principles), this compound acts synergistically with montmorillonite clays enhancing asymmetric epoxidation yields by up to ~6-fold compared to traditional methods according findings presented at ACS National Meetings Spring Conference series held May-June periods annually since their reintroduction post-pandemic restrictions lifted fully last year per organizational records maintained on their official websites accessed via institutional subscriptions available globally except restricted regions per export compliance regulations which do not apply here given our focus on non-regulated substances).

• 92867-45-3(&nbsp;)
• 3658-93-3(1,1-Diethoxyhexane)
• 54815-13-3(Nonanal diethyl acetal)
• 94023-66-2(Nonane,1,1-bis(heptyloxy)-)
• 93892-07-0(1,1-dibutoxyhexane)
• 34764-02-8(Decane, 1,1-diethoxy-)
• 54889-48-4(1,1-diethoxyoctane)
• 94291-88-0(Undecane,1-(decyloxy)-1-methoxy-)
• 18545-17-0(5,5-Diethoxypentan-1-ol)
• 68527-82-2(1,1-bis(octyloxy)octane)