
Tyramine hydrochloride | CAS 60-19-5
| Catalog Number | F10-0133 |
| Category | ATTO Dyes |
| Molecular Formula | C8H11NO·HCl |
| Molecular Weight | 173.64 |
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Product Introduction
Tyramine hydrochloride is a biochemical reagent that features an aromatic amine structure, making it suitable for conjugation in fluorescence labeling applications. It serves as a precursor in the synthesis of various fluorescent dyes and probes, where its reactivity with phenolic groups is leveraged for covalent bonding in enzymatic labeling techniques. In research contexts, tyramine hydrochloride is often utilized in the development of tyramide signal amplification (TSA) assays, enhancing detection sensitivity in fluorescence microscopy and other imaging methodologies.
Chemical Information
Product Specification
Application
Computed Properties
Literatures
Patents
Chemical Information
| Synonyms | 4-(2-Aminoethyl)phenol hydrochloride; 4-Hydroxyphenethylamine hydrochloride |
| Purity | 98.0% |
| IUPAC Name | 4-(2-aminoethyl)phenol;hydrochloride |
| SMILES | C1=CC(=CC=C1CCN)O.Cl |
| InChI | InChI=1S/C8H11NO.ClH/c9-6-5-7-1-3-8(10)4-2-7;/h1-4,10H,5-6,9H2;1H |
| InChIKey | RNISDHSYKZAWOK-UHFFFAOYSA-N |
| Melting Point | 271-274 °C (lit.) |
| MDL Number | MFCD00012901 |
| NACRES | NA.77 |
Product Specification
| Storage | Store at 2-8 °C |
| Signal | Warning |
| GHSHazardStatements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (41.71%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Application
Tyramine hydrochloride is a biogenic amine salt commonly used as a small-molecule handle in chemical biology workflows that require controlled conjugation to proteins, peptides, or biomaterials. In fluorescence and labeling contexts, tyramine derivatives are frequently employed to generate enzyme-mediated or polymer-assisted tagging reagents, enabling downstream attachment of reporter groups to complex targets while maintaining compatibility with common imaging and assay formats.
1. Enzyme-Mediated Protein Labeling
Tyramine hydrochloride is used in labeling workflows where tyramine serves as a substrate or precursor for enzymatic conjugation strategies, allowing incorporation of reporter moieties onto proteins under mild conditions. Researchers in proteomics sample preparation and molecular imaging reagent development rely on tyramine-based tagging to build labeled protein conjugates that can be carried into fluorescence microscopy, immunostaining workflows, and assay development. In these applications, tyramine hydrochloride functions as a practical building block for preparing tyramine-containing labeling reagents that integrate with enzymatic labeling systems to generate stable reporter-bearing biomolecules.
2. Biomaterial Surface Functionalization
Tyramine hydrochloride is applied in materials science and biomaterials research to support surface modification strategies that introduce reactive or label-bearing functionalities onto polymers and coatings. Teams developing functional hydrogels, biointerfaces, and immobilized biomolecule platforms use tyramine-based chemistry to create surfaces that can be further decorated with fluorescent reporters or affinity components for visualization and characterization. This use case is particularly relevant when researchers need a small, well-defined amine salt that can be incorporated into surface functionalization schemes to produce consistent labeling density and robust attachment of subsequent tags.
3. Fluorescent Reporter Conjugate Preparation
Tyramine hydrochloride is frequently used upstream in the preparation of fluorescent labeling reagents and conjugates, where tyramine provides a convenient chemical handle to install fluorophores onto protein targets or onto reporter-carrying constructs. In fluorescence assay development and microscopy reagent preparation, labeled conjugates generated from tyramine-based tagging workflows are used to track biomolecular interactions, monitor binding events, and support imaging-based readouts. This application benefits from tyramine's role as a compact conjugation unit that can be integrated into labeling reagent design while remaining compatible with standard fluorescence detection instrumentation.
4. Polymer and Hydrogel Tagging
Tyramine hydrochloride supports polymer and hydrogel modification workflows where incorporation of tyramine-derived functionality enables later attachment or presentation of fluorescent or affinity reporters within a 3D matrix. Biomaterials groups use tyramine-based functionalization to create labeled scaffolds for imaging studies, material characterization, and controlled presentation of biochemical signals. By enabling reporter installation into polymer networks, tyramine hydrochloride helps researchers generate fluorescently traceable biomaterial platforms used in microscopy-based localization and fluorescence readout assays.
Computed Properties
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Exact Mass | 173.0607417 g/mol |
| Monoisotopic Mass | 173.0607417 g/mol |
| Topological Polar Surface Area | 46.2Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 87.3 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 2 |
| Compound Is Canonicalized | Yes |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 23129510 | 2013-01-01 | Molecular cloning and pharmacological characterisation of a tyramine receptor from the rice stem borer, Chilo suppressalis (Walker) | Pest management science |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| EP-4105323-A1 | New microbial diamine oxidase derived from yarrowia lipolytica for the degradation of biogenic amines | 2021-06-15 |
| WO-2022263031-A1 | New microbial diamine oxidase derived from yarrowia lipolytica for the degradation of biogenic amines | 2021-06-15 |
| KR-20220166396-A | Fire extinguishing product to prevent fire caused by transformer insulating oil | 2021-06-09 |
| WO-2022170012-A1 | Synthesis of peg-based thiol-norbornene hydrogels with tunable hydroylitic degradation properties | 2021-02-08 |
| WO-2022099195-A1 | Ophthalmic formulation containing a dopaminergic prodrug that may be combined with one or more agents | 2020-11-09 |
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