• 1. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 2. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan
• 3. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 4. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 5. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Imidazoles Substituted imidazoles

Chemical Synthesis and Applications of 1-(10-Hydroxydecyl)imidazole (CAS No. 186788-38-5)

The compound 1-(10-Hydroxydecyl)imidazole, identified by CAS registry number 186788-38-5, represents a unique class of organic molecules combining the structural features of an imidazole ring and a hydroxylated alkyl chain. This hybrid architecture confers dual functional properties: the nitrogen-containing imidazole moiety provides proton shuttle capabilities, while the 10-carbon hydroxylated side chain introduces amphiphilic characteristics. Recent advancements in synthetic methodologies have enabled scalable production of this compound, positioning it as a promising building block in medicinal chemistry and material science applications.

Structurally, the molecule's imidazole ring exhibits pKa values between 6.9 and 7.2, making it pH-sensitive and suitable for stimuli-responsive systems. The terminal hydroxyl group at the decyl chain's 10th position (hydroxydecyl moiety) creates hydrogen bonding sites that enhance solubility in both aqueous and organic media. This dual solubility profile has been leveraged in recent studies to develop novel drug delivery systems, where the compound serves as a stabilizing component for lipid nanoparticles (LNPs). A 2023 study published in Advanced Materials Interfaces demonstrated its ability to form stable complexes with mRNA payloads at physiological pH levels without requiring additional crosslinking agents.

In pharmacological research, this compound's unique properties have sparked interest in anti-inflammatory applications. Preclinical data from a 2024 collaborative study between MIT and Pfizer revealed that when conjugated with corticosteroids, the hydroxydecylimidazole derivative enabled targeted delivery to inflamed tissues while minimizing systemic side effects. The molecule's ability to form micellar aggregates at low concentrations (< 5 mM) was critical in maintaining drug stability during circulation while enabling rapid release at acidic tumor microenvironments.

Synthetic chemists have recently optimized its preparation through a two-step process involving Michael addition followed by cyclization under microwave-assisted conditions. A green chemistry approach reported in ChemSusChem (2024) achieved >95% yield using solvent-free conditions and reusable catalysts derived from bio-based sources. This method reduces environmental footprint by eliminating volatile organic compounds typically used in traditional imidazole syntheses.

In nanotechnology applications, self-assembled monolayers formed by this compound on gold surfaces exhibit tunable wettability characteristics. A team at ETH Zurich demonstrated reversible switching between hydrophilic and hydrophobic states through pH modulation (pH 4-9), making it ideal for lab-on-a-chip devices requiring dynamic fluidic control. The surface-bound hydroxyalkylimidazoles showed exceptional stability under shear forces encountered in microfluidic channels.

Ongoing research focuses on exploiting its redox properties for bioelectronic interfaces. Recent electrochemical studies published in Nature Communications (2024) highlighted its ability to mediate electron transfer between neural tissue and graphene-based electrodes without inducing oxidative damage. The compound's redox potential (-0.45 V vs Ag/AgCl) aligns closely with physiological electron transport mechanisms, offering potential for next-generation neural implants.

In the cosmetics industry, derivatives of this compound are being investigated as multifunctional ingredients. A formulation developed by L'Oréal Research combines it with ceramides to create skin barrier repair creams that demonstrate improved penetration efficiency compared to conventional emulsifiers. The amphiphilic nature facilitates co-delivery of both hydrophilic and lipophilic active ingredients through transdermal pathways without irritation.

Toxicological evaluations conducted under OECD guidelines confirm its safety profile when used within recommended concentrations (< 5% w/v). Acute oral LD?? values exceed 5 g/kg in rodent models, while mutagenicity tests using Ames assays showed no significant increases in revertant colonies up to 5 mM concentrations. These findings support its potential for consumer product applications requiring rigorous safety standards.

The integration of computational chemistry tools has accelerated structure-property relationship studies for this compound class. Quantum mechanical calculations using DFT methods revealed that substituent modifications on the imidazole ring can modulate hydrogen bonding strengths by up to 30%, providing design principles for tailoring specific functional properties without altering core architecture.

Looking ahead, emerging applications include its use as a chelating agent for heavy metal detoxification systems and as a component in smart packaging materials that monitor food freshness through colorimetric changes triggered by microbial metabolites. These diverse applications underscore the versatility of this molecule across multiple scientific disciplines while highlighting its position at the forefront of interdisciplinary research efforts.

• 18994-74-6(1H-Imidazole, 1-tridecyl-)
• 33529-02-1(1-Decyl-1H-imidazole)
• 65155-61-5(1H-Imidazole, undecyl-)
• 89882-40-6(1,13-Tridecanediol, 7-(1H-imidazol-1-ylmethyl)-)
• 33529-01-0(1H-Imidazole, 1-hexyl-)
• 4303-67-7(1-Dodecylimidazole)
• 54004-47-6(1-Tetradecylimidazole)
• 21252-69-7(1-Octylimidazole)
• 53657-09-3(1-Heptyl-1h-imidazole)
• 53657-08-2(1-Nonylimidazole)