13-Tetradecynoic Acid | CAS 82909-47-5

13-Tetradecynoic Acid is a long-chain terminal alkyne fatty acid designed for bioorthogonal click chemistry workflows, most commonly used as a chemical handle in copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and related alkyne-based conjugations. Its hydrophobic, lipid-like structure enables incorporation into lipid-modified systems and membrane-associated labeling strategies, while the terminal alkyne provides a reactive site for downstream attachment of azide-bearing reporters, biomolecules, or polymeric tags. As a research-grade alkyne lipid building block, 13-Tetradecynoic Acid is widely used to generate clickable analogs for imaging, materials functionalization, and labeling of lipid-containing assemblies.

1. Membrane Imaging Labeling

13-Tetradecynoic Acid is used as a clickable fatty-acid analog to introduce terminal alkyne functionality into lipid-rich membranes and membrane mimetics, enabling subsequent conjugation with azide-functional fluorescent dyes or affinity tags. Researchers employ this approach to visualize membrane localization, track lipid remodeling in cultured systems, and map membrane-associated processes using standardized CuAAC labeling steps. The long alkyl chain supports membrane partitioning and compatibility with lipid environments, making 13-Tetradecynoic Acid a practical reagent for generating alkyne-bearing lipid probes for microscopy and flow-based readouts.

2. Lipidomics And Metabolic Probes

13-Tetradecynoic Acid serves as a metabolic labeling tool in studies that require downstream click derivatization for detection, enrichment, or reporter installation on lipid species. After incorporation into lipid pools, the terminal alkyne enables selective attachment of azide-tagged handles such as biotin for affinity capture or fluorophores for visualization, supporting workflows that combine chemical labeling with analytical readouts. This reagent is frequently selected when researchers need a robust, widely compatible alkyne tag that can be coupled to azide reagents under CuAAC conditions for sensitive downstream processing.

3. Biomaterials Surface Functionalization

13-Tetradecynoic Acid is applied to functionalize polymeric or composite biomaterials with alkyne groups that can be further coupled to azide-bearing ligands, crosslinkers, or bioactive motifs via click chemistry. Long-chain fatty-acid chemistry supports incorporation into hydrophobic coatings, lipid-like layers, or amphiphilic material surfaces, allowing researchers to create clickable interfaces for subsequent conjugation. This enables modular assembly of patterned surfaces, immobilized capture reagents, and multicomponent material architectures using azide-functional partners.

4. Polymer And Nanoparticle Conjugation

13-Tetradecynoic Acid is used as a hydrophobic alkyne building block to introduce clickable functionality into nanoparticle formulations and polymer conjugates that contain lipid-compatible domains. By providing a terminal alkyne moiety, 13-Tetradecynoic Acid supports post-assembly coupling to azide-functional dyes, targeting ligands, or imaging reporters, facilitating modular probe generation without redesigning the core material. Common downstream uses include preparing fluorescent or affinity-tagged nanoparticle systems and constructing multivalent conjugates for research imaging and assay development.