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HomeProduct name listNile Red

Nile Red

Synonym(s):Nile Blue A Oxazone

  • CAS NO.:7385-67-3
  • Empirical Formula: C20H18N2O2
  • Molecular Weight: 318.37
  • MDL number: MFCD00011639
  • EINECS: 230-966-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Nile Red  Structural

What is Nile Red ?

Description

Nile red is a dye based on the benzo[a]phenoxazine core. Nile Red (9-diethylbenzo[a]phenoxazin-5- one) stands out as electrically neutral and water-insoluble since it features a carbonyl group at the 5-position that readily accepts the electron density. This makes it a strong push?pull chromophore, which underlies its distinct solvatochromicity and ability to indicate, e.g., cellular events in live-cell imaging. In addition, Nile Red’s inherent lipophilicity, near-infrared (NIR) emission, large Stokes shift, two-photon absorptivity (2PA), and low background fluorescence (as the luminosity is quenched in aqueous (aq) media) render it a near-ideal histochemical stain for studying membranes and lipid droplets in cells. The increase of its exquisite solvent sensitivity and steep emission in hydrophobic environments has also been employed in various forms of stochastic super-resolution localization microscopy[1].

Chemical properties

solid

The Uses of Nile Red

Nile red is a lipophilic stain. Nile red stains intracellular lipid droplets. Nile red is also intensely fluorescent, with a strong yellow-gold emission if included into a lipid-rich environment.

The Uses of Nile Red

Nile Red is a photostable, lipophilic stain with bright red fluorescence. Dyes and metabolites.

What are the applications of Application

Nile Red is a photostable, lipophilic stain with bright red fluorescence that has been used stain cell structures to visualize and localize colloidal drug carriers.

Definition

ChEBI: An organic heterotetracyclic compound that is 5H-benzo[a]phenoxazin-5-one substituted at position 9 by a diethylamino group.

General Description

Nile Red is an uncharged hydrophobic molecule and a benzophenoxazone dye. 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.

Synthesis

Using the 1,3-Naphthalenediol Approach to synthsis Nile red. To a solution of 1,3-naphthalenediol (0.50 g, 3.12 mmol) in anhydrous DMF (25 mL) was added 4-nitroso-N,N-diethylaniline (0.56 g, 3.12 mmol). This reaction mixture was stirred at 80 °C (DrySyn heating block) for 16 h and concentrated under reduced pressure. The crude product was purified by flash chromatography (0?50% EtOAc in hexanes) to obtain Nile Red, which crystallized from hexanes in green crystals (0.80 g, 2.50 mmol). Yield: 80%[1].

storage

Room temperature

References

[1] Mick Hornum*. “Substituted 9-Diethylaminobenzo[a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties.” The Journal of Organic Chemistry 86 2 (2020): 1471–1488.

Properties of Nile Red

Melting point: 203-205 °C(lit.)
Boiling point: 457.53°C (rough estimate)
Density  1.1871 (rough estimate)
refractive index  1.5700 (estimate)
storage temp.  2-8°C
solubility  methanol: soluble1mg/mL
form  Powder
pka 4.08±0.20(Predicted)
color  Dark red to maroon
BRN  279110
Stability: Stable. Incompatible with strong oxidizing agents.
InChI 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
CAS DataBase Reference 7385-67-3(CAS DataBase Reference)
EPA Substance Registry System 5H-Benzo[a]phenoxazin-5-one, 9-(diethylamino)- (7385-67-3)

Safety information for Nile Red

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Nile Red

InChIKey VOFUROIFQGPCGE-UHFFFAOYSA-N
SMILES C12=CC=CC=C1C(=O)C=C1C2=NC2=C(C=C(N(CC)CC)C=C2)O1

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