Coumarin 6

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Coumarin 6

Coumarin 6 | 38215-36-0

Catalog Number A17-0001
Category Coumarin
Molecular Formula C20H18N2O2S
Molecular Weight 350.43
Catalog Number Size Price Quantity
A17-0001 -- $--

Product Introduction

Coumarin 6 is a fluorescent dye that has been widely used in cell imaging and flow cytometry due to its excellent photostability. The cell membrane staining capabilities of Coumarin 6 not only facilitate complex visualization of cell morphology but also enable precise assessment of membrane integrity. This dye shows promising applications in drug delivery systems and bioimaging technology, helping to explore a variety of diseases and unravel the mystery of drug efficacy.

Chemical Information

Synonyms Coumarin 540;3-(2-benzothiazolyl)-7-(diethylamino)-2H-1-benzo-pyran-2-one; Coumarin 153; Coumarin 6
Purity ≥99%
IUPAC Name 3-(1,3-benzothiazol-2-yl)-7-(diethylamino)chromen-2-one
Canonical SMILES CCN(CC)C1=CC2=C(C=C1)C=C(C(=O)O2)C3=NC4=CC=CC=C4S3
InChI InChI=1S/C20H18N2O2S/c1-3-22(4-2)14-10-9-13-11-15(20(23)24-17(13)12-14)19-21-16-7-5-6-8-18(16)25-19/h5-12H,3-4H2,1-2H3
InChI Key VBVAVBCYMYWNOU-UHFFFAOYSA-N
Solubility soluble in Dimethylformamide,Alcohol
Appearance Light yellow to Brown powder to crystal
Melting Point 208 °C
  • Product Specification
  • Application
Storage Keep in dark place.
Signal Warning
GHS Hazard Statements H302 (33.33%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (33.33%): Harmful in contact with skin [Warning Acute toxicity, dermal] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H332 (33.33%): Harmful if inhaled [Warning Acute toxicity, inhalation] H335 (66.67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement Codes P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, 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.)

Coumarin 6, a highly sought-after fluorescent dye, boasts distinctive optical characteristics that make it indispensable in various scientific domains. Here are four key applications of Coumarin 6:

Cell Imaging: At the forefront of cell imaging methodologies, Coumarin 6 plays a pivotal role in visualizing intricate cellular structures and dynamic processes. Its robust fluorescence properties facilitate unparalleled high-resolution imaging, crucial for scrutinizing cell morphology, organelle dynamics, and intracellular pathways. Researchers leverage its capabilities to monitor and quantify real-time cellular events with exceptional clarity, shedding light on the inner workings of cells with remarkable detail.

Drug Delivery Studies: Coumarin 6 emerges as a vital tool in drug delivery investigations, serving as a fluorescent beacon to track the intricate distribution and release dynamics of drug carriers. By conjugating nanoparticles or micelles with Coumarin 6, scientists can meticulously monitor their trafficking and uptake within biological systems. This enables the optimization of drug delivery systems for enhanced target specificity and therapeutic potency, paving the way for refined drug administration approaches.

Microsphere Labeling: Pioneering polymeric microsphere applications, Coumarin 6 is employed to label these microscopic entities for diverse analytical endeavors. These labeled microspheres play a pivotal role in flow cytometry, microscopy, and bioimaging methodologies. The vibrant fluorescence of Coumarin 6 empowers precise detection and quantification of microspheres within complex biological samples, facilitating advanced research in various scientific disciplines.

Photophysics and Photochemistry: Serving as a quintessential model compound in the realm of photophysics and photochemistry, Coumarin 6 is a cornerstone of fluorescence dye research. Researchers delve into its fluorescence quantum yield, lifetime, and stability under varying conditions to glean deep insights into its optical properties. This critical information fuels the development of novel fluorescent probes and unravels fundamental aspects of fluorescence mechanisms, enriching our understanding of light-induced processes at a molecular level.

Computed Properties

XLogP3 4.9
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 5
Rotatable Bond Count 4
Exact Mass 350.10889899 g/mol
Monoisotopic Mass 350.10889899 g/mol
Topological Polar Surface Area 70.7Ų
Heavy Atom Count 25
Formal Charge 0
Complexity 534
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 1
Compound Is Canonicalized Yes

Literatures

PMIDPublication DateTitleJournal
22906968 2012-11-01 A novel luminescent terbium-3-carboxycoumarin probe for time-resolved fluorescence sensing of pesticides methomyl, aldicarb and prometryne Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy
22846410 2012-10-15 Preparation and characterization of teniposide PLGA nanoparticles and their uptake in human glioblastoma U87MG cells International journal of pharmaceutics
22369856 2012-06-14 Hepatocellular carcinoma targeting effect of PEGylated liposomes modified with lactoferrin European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences
22154100 2012-04-01 Enhanced transdermal delivery of indomethacin using combination of PLGA nanoparticles and iontophoresis in vivo Colloids and surfaces. B, Biointerfaces
22385336 2012-03-29 Stimulus-responsive supramolecular pKa tuning of cucurbit[7]uril encapsulated coumarin 6 dye The journal of physical chemistry. B

Patents

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CN-114831926-A A kind of double-layer microneedle array and preparation method thereof 2022-05-09
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