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Merck

442631

Sigma-Aldrich

Coumarin 6

98%

Sinónimos:

3-(2-Benzothiazolyl)-7-(diethylamino)coumarin, 3-(2-Benzothiazolyl)-N,N-diethylumbelliferylamine

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About This Item

Fórmula empírica (notación de Hill):
C20H18N2O2S
Número de CAS:
Peso molecular:
350.43
Beilstein/REAXYS Number:
1085798
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

98%

form

solid

mp

208-210 °C (lit.)

λmax

444 nm

fluorescence

λem 505 nm in ethanol (Lasing peak 534 nm, lasing range 515 - 558 nm (DMSO), pump source XeCl (308 nm))

OLED device performance

ITO/Alq3:Coumarin 6/Mg:Ag

  • Color: green
  • Max. EQE: 2.5 %

SMILES string

CCN(CC)c1ccc2C=C(C(=O)Oc2c1)c3nc4ccccc4s3

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

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General description

Coumarin 6 (C6) is a derivative of coumarin with a benzothiazolyl group at the position 3. It emits fluorescence in solid and solution state and is used as fluorescent dye to stain organelles. C6 is majorly used as blue-green spectrum laser dye and is microenvironment sensitive.
Coumarin 6 is a fluorescent dye that belongs to the 7-diethylaminocoumarin series that can be used in a variety of biological activities. It can be used as a dopant that exhibits green light (500 nm) in optoelectronic applications.

Application

Coumarin 6 dye can be used in the labeling and visualization of polymeric nanoparticles in biological applications, such as oral drug delivery systems for cancer. It can also be used in development of electroluminescent devices such as organic light emitting diodes (OLEDs).
Coumarin 6 has been used as a hydrophobic fluorescent dye
  • in block copolymer (BCP)-based micelle based drug delivery studies in glioma cell lines
  • in combination with flufenamic acid (FA) based nanoprodrug uptake in glioma cells
  • in poly(lactic-co-glycolic acid) (PLGA) based elvitegravir nanoprodrug uptake studies

Laser dye

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

Nanoprodrugs of NSAIDs: Preparation and characterization of flufenamic acid nanoprodrugs
Lee BS, et al.
Journal of Drug Delivery, 2011 (2011)
Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism.
Jones G, et al.
The Journal of Physical Chemistry, 89(2), 294-300 (1985)
Micelle-templated, poly (lactic-co-glycolic acid) nanoparticles for hydrophobic drug delivery
Nabar GM, et al.
International journal of nanomedicine, 13, 351-351 (2018)
Afra Torge et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 104, 171-179 (2017-04-10)
Nano-embedded microparticles represent a promising approach to deliver nanoparticles to the lungs. Microparticles with an appropriate aerodynamic diameter enable an application by dry powder inhaler and the transport of nanoparticles into the airways. By disintegration after deposition, nanoparticles can be
Seungil Kim et al.
Journal of biomaterials science. Polymer edition, 28(17), 2082-2099 (2017-08-31)
New amphiphilic PEGylated poly(aspartic acid) graft copolymer (PASP-PEG-Ph) was synthesized as a nanocarrier for intravaginal drug delivery of poorly water-soluble drugs. PASP-PEG-Ph self-assembled into negatively charged spherically shaped nanoparticles in the presence of pH 4.5 and pH 7.0 vaginal fluid

Artículos

Micelle formation addresses low solubility in IV drug delivery, overcoming clinical limitations.

Micelle formation addresses low solubility in IV drug delivery, overcoming clinical limitations.

Micelle formation addresses low solubility in IV drug delivery, overcoming clinical limitations.

Micelle formation addresses low solubility in IV drug delivery, overcoming clinical limitations.

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