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3,3'-Dihexyloxacarbocyanine iodide | CAS 53213-82-4
| Catalog Number | A16-0048 |
| Category | Endoplasmic Reticulum Fluorescent Probes |
| Molecular Formula | C29H37IN2O2 |
| Molecular Weight | 572.5 |
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Product Introduction
3,3'-Dihexyloxacarbocyanine iodide is a lipophilic fluorescent dye belonging to the cyanine class, characterized by its extended conjugated system that facilitates strong absorption and emission in the near-infrared region. It is commonly used as a membrane probe due to its ability to integrate into lipid bilayers, providing valuable insights into membrane dynamics and potential changes in cellular environments. The dye's spectral properties make it suitable for applications in fluorescence microscopy and flow cytometry, where it aids in visualizing and tracking cellular and subcellular structures.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | 3-hexyl-2-[3-(3-hexyl-2(3H)-benzoxazolylidene)-1-propen-1-yl]-benzoxazolium, iodide |
| Purity | ≥98% |
| IUPAC Name | (2Z)-3-hexyl-2-[(E)-3-(3-hexyl-1,3-benzoxazol-3-ium-2-yl)prop-2-enylidene]-1,3-benzoxazole;iodide |
| SMILES | CCCCCCN1C2=CC=CC=C2OC1=CC=CC3=[N+](C4=CC=CC=C4O3)CCCCCC.[I-] |
| InChI | InChI=1S/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1 |
| InChIKey | XVLXYDXJEKLXHN-UHFFFAOYSA-M |
| Appearance | Solid Powder |
Product Specification
| Excitation | 484 nm |
| Emission | 501 nm |
| Storage | Store at -20°C |
| Signal | Warning |
| GHSHazardStatements | H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): 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
3,3’-Dihexyloxacarbocyanine iodide (commonly known as DiOC6) is a fluorescent dye used extensively in bioscience research. Here are some key applications of 3,3’-Dihexyloxacarbocyanine iodide:
Mitochondrial Membrane Potential Measurement: DiOC6 is frequently used to assess mitochondrial membrane potential in live cells. By accumulating in mitochondria, the dye allows researchers to visualize and quantify changes in membrane potential. This application is vital for studying mitochondrial function and diagnosing mitochondrial diseases.
Cell Membrane Staining: DiOC6 is suitable for staining cell membranes, making it a valuable tool for fluorescence microscopy and flow cytometry. The dye aids in identifying and distinguishing different cell populations based on membrane characteristics. This application is particularly useful in immunology and cancer research, where cell membrane properties are key biomarkers.
Live Cell Imaging: DiOC6 can be used in live cell imaging to monitor intracellular structures and processes in real-time. Its compatibility with various imaging techniques makes it a versatile dye for studying cellular dynamics. Researchers can track cell morphology, migration, and interactions, providing insights into cellular behavior under various conditions.
Apoptosis Detection: DiOC6 dye can be employed to detect apoptosis by measuring disruptions in mitochondrial membrane potential, an early event in programmed cell death. This application is crucial for understanding the mechanisms of apoptosis and evaluating the efficacy of anti-cancer drugs. By detecting early apoptosis, researchers can also study cell survival and death pathways, contributing to targeted therapy development.
Computed Properties
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 12 |
| Exact Mass | 572.18998 g/mol |
| Monoisotopic Mass | 572.18998 g/mol |
| Topological Polar Surface Area | 29.5Ų |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Complexity | 581 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 2 |
| Compound Is Canonicalized | Yes |
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