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Merck
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N3013

Nile Red

Powder

Synonym(s):

9-(diethylamino)-5H-benzo[a]phenoxazin-5-one, 9-(diethylamino)benzo[a]phenoxazin-5-one, Nile Blue A Oxazone

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About This Item

Empirical Formula (Hill Notation):
C20H18N2O2
CAS Number:
7385-67-3
Molecular Weight:
318.37
NACRES:
NA.47
PubChem Substance ID:
24897612
UNSPSC Code:
12171500
EC Number:
230-966-0
MDL number:
MFCD00011639
Beilstein/REAXYS Number:
279110

Key Documents

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Product Name

Nile Red, Technical grade

grade

technical grade

Quality Level

200

form

powder

composition

Carbon: 70.0-77.3%

Nitrogen: 7.5-8.8%

technique(s)

titration: suitable

mp

203-205 °C (lit.)

solubility

methanol: 1 mg/mL

λmax

553 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

CCN(CC)c1ccc2N=C3C(Oc2c1)=CC(=O)c4ccccc34

InChI

1S/C20H18N2O2/c1-3-22(4-2)13-9-10-16-18(11-13)24-19-12-17(23)14-7-5-6-8-15(14)20(19)21-16/h5-12H,3-4H2,1-2H3

InChI key

VOFUROIFQGPCGE-UHFFFAOYSA-N

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General description

Nile Red is a lipophilic fluorescent benzophenoxazone dye that is metachromatic and solvatochromic. It is an uncharged hydrophobic molecule with the ability to stain and visualize lipid droplets in cells and tissues. It functions as a fluorescent probe for intracellular lipids and hydrophobic domains of proteins. This dye is fluorescent in all organic solvents. Its fluorescence colors range from golden yellow to deep red.

Application

Nile red is widely employed in studies related to lipid metabolism, lipid droplet dynamics, lipid accumulation in cells or tissues, and lipid-based drug delivery systems. Its other applications include:
  • identification of microplastics in routine analysis of biological samples.
  • detection of lysosomes and lysosome-related organelles, like gut granules in C. elegans intestinal cells.
  • it exhibits strong fluorescence enhancement and is used for staining SDS (sodium dodecyl sulphate) gels.

Biochem/physiol Actions

Nile Red is lipophilic in nature and exploits the hydrophobic properties of molecules such as lipids and plastics that fluoresce when excited with certain wavelengths, facilitating quantification and identification.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT0228
SHBS6175
SLBP9326V
070K3462
063K3730

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Luca Nalbone et al.
Marine pollution bulletin, 172, 112888-112888 (2021-08-29)
Nile Red is a lipophilic, metachromatic and solvatochromic dye used as an alternative or complementary method to aid identification of microplastics in routine analysis of biological samples. It was rarely used in biota since organic residues after the digestion step
Zebrafish obesogenic test: a tool for screening molecules that target adiposity.
Tingaud-Sequeira A
Journal of Lipid Research, 52, 1765-1765 (2011)
D L Sackett et al.
Analytical biochemistry, 167(2), 228-234 (1987-12-01)
Nile red is an uncharged hydrophobic molecule whose fluorescence is strongly influenced by the polarity of its environment. It interacts with many, but not all, native proteins, including beta-lactoglobulin, kappa-casein, and albumin, with a wide range of spectral changes for
Protein gel staining methods: an introduction and overview
Thomas H Steinberg
Methods in Enzymology, 541-563 (2009)
Hanna Fares et al.
Methods in cell biology, 107, 239-263 (2012-01-10)
This chapter describes methods for studying membrane traffic and organelle biogenesis in Caenorhabditis elegans. These processes have traditionally been studied with yeast or mammalian cells, but C. elegans is emerging as an attractive alternative model system for cell biologists. C.
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Global Trade Item Number

SKUGTIN
N3013-100MG04061833742082
N3013-1G04061834115632

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