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442631

Sigma-Aldrich

Coumarin 6

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H18N2O2S
CAS Number:
Molecular Weight:
350.43
Beilstein:
1085798
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23
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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[1] and is used as fluorescent dye to stain organelles.[2] C6 is majorly used as blue-green spectrum laser dye and is microenvironment sensitive.[3]
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.[4][5][6]

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.[7] It can also be used in development of electroluminescent devices such as organic light emitting diodes (OLEDs).[8][9]
Coumarin 6 has been used as a hydrophobic fluorescent dye
  • in block copolymer (BCP)-based micelle based drug delivery studies in glioma cell lines[10]
  • in combination with flufenamic acid (FA) based nanoprodrug uptake in glioma cells[11]
  • in poly(lactic-co-glycolic acid) (PLGA) based elvitegravir nanoprodrug uptake studies[12]

Laser dye

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Surface modification of indium tin oxide by plasma treatment: An effective method to improve the efficiency, brightness, and reliability of organic light emitting devices.
Wu CC, et al.
Applied Physics Letters, 70(11), 1348-1350 (1997)
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
Micelle-templated, poly (lactic-co-glycolic acid) nanoparticles for hydrophobic drug delivery
Nabar GM, et al.
International journal of nanomedicine, 13, 351-351 (2018)
Synthesis and anti-angiogenesis activity of coumarin derivatives.
Lee S, et al.
Bioorganic & Medicinal Chemistry Letters, 16(17), 4596-4599 (2006)
Nanoprodrugs of NSAIDs: Preparation and characterization of flufenamic acid nanoprodrugs
Lee BS, et al.
Journal of Drug Delivery, 2011 (2011)

Articles

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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Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Coumarin6에 대한 질문입니다. 1. 빛, 수분 민감성에 대한 report가 있나요 ? -. 빛, 수분을 받으면 색상이 더 붉은색으로 변하는지? 2. 저희 제품에 색상 부여용으로 사용하고 있는데, 저희 재료와 뭉침 현상이 발생합니다. 그결과, 주황이물(1um)이 생기는데, 빛 영향이 있나요 ? 사례가 있는지?

    1 answer
    1. As mentioned in section 7 of the product Safety Data Sheet, this chemical is light-sensitive.

      To further discuss this issue you are reporting, please contact our Technical Service team who can assist you with further troubleshooting and/or investigation.

      We kindly ask you to navigate to the link https://www.sigmaaldrich.com/techservice and click on "Report Product Issues" under the Products Section with all the required information so that a member of our team can reach out to you to assist further.

      Please note that this product is intended for research use only and is not to be used for any other purpose, which includes but is not limited to, unauthorized commercial uses, in vitro diagnostic uses, ex vivo or in vivo therapeutic uses, or any type of consumption or application to humans or animals.

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