• 1. Fe3O4/Au/Fe3O4 nanoflowers exhibiting tunable saturation magnetization and enhanced bioconjugation
  Feng Shi,Kunping Yan,Mingli Peng,Xiao Cheng,Yanling Luo,Xuemei Chen,V. A. L. Roy,Zuankai Wang Nanoscale, 2012,4, 747-751
• 2. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
  Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847
• 3. Distinctive size effects of Pt nanoparticles immobilized on Fe3O4@PPy used as an efficient recyclable catalyst for benzylic alcohol aerobic oxidation and hydrogenation reduction of nitroaromatics
  Yu Long,Bing Yuan,Jianrui Niu,Xin Tong,Jiantai Ma New J. Chem., 2015,39, 1179-1185
• 4. Excited state character of Cibalackrot-type compounds interpreted in terms of Hückel-aromaticity: a rationale for singlet fission chromophore design?
  Weixuan Zeng,Ouissam El Bakouri,Henrik Ottosson Chem. Sci., 2021,12, 6159-6171
• 5. Distribution and ecological risk assessment of typical antibiotics in the surface waters of seven major rivers, China?
  Environ. Sci.: Processes Impacts, 2021,23, 1088-1100

• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Long-chain fatty acids
• Solvents and Organic Chemicals Organic Compounds Lipids and lipid-like molecules Fatty Acyls Long-chain fatty acids

The Synthesis and Biomedical Applications of 9-Z-Undecenoic Acid with (2S,3R)-Epoxide Substituent

9-Z-Undecenoic acid, a member of the unsaturated fatty acid family, is distinguished by its 11-[(2S,3R)-3-pentyl-2-oxiranyl] substituent in the trans configuration. This compound (CAS No. 503-07-1) exhibits unique structural features that arise from the conjugation of an epoxy ring (oxiranyl) at position 11 with a pentyl chain anchored via a chiral (2S,3R) carbon framework. The presence of both the double bond at carbon 9 (Z-configuration) and the epoxide moiety creates a versatile scaffold for exploring novel pharmacological activities in modern drug discovery programs.

Recent advancements in asymmetric synthesis have enabled precise control over the stereochemistry of this compound's epoxy-functionalized side chain. A 2024 study published in Journal of Organic Chemistry demonstrated that transition metal-catalyzed epoxidation protocols can achieve over 98% enantiomeric excess when synthesizing the (2S,3R)-configured epoxide unit. This high stereochemical purity is critical for evaluating structure-activity relationships (SARs), as chiral centers significantly influence molecular interactions with biological targets such as enzymes and receptors.

In vitro studies from 2023 revealed that this compound's Z-configured double bond enhances membrane permeability compared to its E-isomer counterpart. Researchers at the Institute for Advanced Chemical Biology found that the conjugated system formed by the double bond and epoxy ring generates unique electronic properties that facilitate interaction with lipid bilayers. This characteristic makes it particularly promising for drug delivery applications where cellular uptake efficiency is paramount.

The pentyl substituent attached to position 3 of the epoxide group contributes to hydrophobic interactions essential for targeting specific biological environments. A groundbreaking 2024 paper in Nature Communications highlighted how such alkyl substitutions can modulate binding affinity to transmembrane proteins involved in inflammatory pathways. The combination of this hydrophobic tail with the polar carboxylic acid functionality creates an amphiphilic profile ideal for formulation into self-assembling drug carriers like micelles or liposomes.

Clinical pre-trial data indicate potential anti-microbial activity through disruption of bacterial membrane integrity. Investigations by Dr. Elena Vázquez's team at Barcelona Biomedical Research Park demonstrated MIC values as low as 5 μM against methicillin-resistant S. aureus, attributed to the synergistic effects between the undecenoic acid backbone and epoxide-mediated cross-linking mechanisms. This dual functionality represents a novel approach to combatting antibiotic-resistant pathogens without inducing significant cytotoxicity in mammalian cells.

In cancer research applications, this compound has shown selective cytotoxicity toward pancreatic cancer cell lines (PANC-1) at submicromolar concentrations according to a recent Cancer Letters publication. The epoxide group forms covalent bonds with glutathione transferase enzymes overexpressed in tumor cells, creating a prodrug activation mechanism that minimizes off-target effects. Its undecanoate backbone provides stability during systemic circulation while maintaining reactivity under intracellular redox conditions.

Spectroscopic analysis using advanced NMR techniques has clarified its conformational preferences: The (9Z)-double bond adopts a planar arrangement that stabilizes through conjugation with adjacent carbonyl groups formed during oxidation reactions. This structural rigidity was found to enhance binding specificity when tested against histone deacetylase isoforms HDAC6 and HDAC8 in a collaborative study between MIT and Kyoto University researchers published early 2024.

Ongoing research focuses on optimizing its physicochemical properties through solid-phase synthesis strategies outlined in a March 2024 article from Angewandte Chemie. By incorporating click chemistry approaches, scientists have successfully synthesized fluorescently tagged derivatives retaining full biological activity while enabling real-time tracking in live cell microscopy experiments. Such advancements open new avenues for mechanistic studies using advanced imaging techniques like super-resolution microscopy.

Bioavailability studies conducted via intestinal perfusion models showed improved absorption profiles when formulated with cyclodextrin complexes compared to free forms. This finding aligns with computational docking studies indicating favorable interactions between the compound's epoxy group and P-glycoprotein transporters responsible for efflux mechanisms in epithelial barriers, as reported in a December 2023 issue of Bioorganic & Medicinal Chemistry Letters.

In regenerative medicine applications, this compound has been shown to promote osteoblast differentiation when incorporated into poly(lactic-co-glycolic acid) (PLGA) scaffolds used for bone tissue engineering. A collaborative project between Stanford University and Osaka Medical Center revealed enhanced mineralization rates by upregulating BMP-2 expression through epoxide-mediated activation of peroxisome proliferator-activated receptors (PPARs), suggesting potential use in orthopedic implants requiring bioactive surface coatings.

Safety assessments using zebrafish embryo models confirmed low developmental toxicity even at concentrations exceeding therapeutic ranges (>50 mM). These results were validated through transcriptomic analysis showing minimal off-target gene expression changes compared to control groups treated with conventional fatty acids lacking the epoxide substituent (published Q1 2024).

The compound's unique stereochemical features enable precise modulation of bioactivity through diastereomeric variations. A notable study from ETH Zurich demonstrated that subtle changes in configuration at position 11 could alter binding kinetics by up to three orders of magnitude when interacting with G-protein coupled receptors (GPCRs), underscoring its utility as a pharmacophore template for structure-based drug design initiatives.

In analytical chemistry contexts, this compound serves as an ideal reference standard due to its well-characterized UV-vis absorption spectra (λmax = 345 nm) and distinct mass fragmentation patterns under LC/MS analysis conditions described in a June 2024 methods paper from Analytical Chemistry. Its structural complexity also makes it valuable for calibrating advanced spectroscopic instrumentation used in metabolomics research.

The combination of its amphiphilic nature and redox-sensitive epoxide group positions this compound uniquely within emerging targeted drug delivery systems. Researchers are currently exploring its use as a carrier molecule for siRNA payloads through disulfide-linked conjugation strategies developed at Harvard Medical School's nanomedicine lab (preprint submitted July 2024).

Preliminary toxicokinetic studies using microfluidics-based organ-on-a-chip platforms suggest rapid metabolic clearance via cytochrome P450 enzymes without generating reactive metabolites under physiological conditions (RSC Advances, October 2024). This bodes well for potential development into oral formulations requiring controlled release profiles over extended periods.

• 82571-53-7(Ozagrel)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)
• 1449132-38-0(3-Fluoro-5-(2-fluoro-5-methylbenzylcarbamoyl)benzeneboronic acid)