61419-02-1

Basic information

• Product Name: NAPHTHOFLUORESCEIN
• Synonyms: NAPHTHOFLUORESCEIN;NAPHTHOFLUORESCEIN, FOR FLUORESCENCE;NAPHTHOFLUORESCEIN FOR FLUORESCENCE 95+%;Naphthafluorescein;Spiro[7H-dibenzo[c,h]xanthene-7,1'(3'H)-isobenzofuran]-3'-one,3,11-dihydroxy-
• CAS NO: 61419-02-1
• Molecular Formula: C₂₈H₁₆O₅
• Molecular Weight: 432.429
• EINECS: 257-250-0
• Mol File: 61419-02-1.mol

Chemical Properties

• Melting Point: 189 °C (dec.)(lit.)
• Boiling Point: 755.5°C at 760 mmHg
• Flash Point: 266.3°C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 1.27E-23mmHg at 25°C
• Refractive Index: 1.86
• Solubility: DMF: soluble
• BRN: 61335
• CAS DataBase Reference: NAPHTHOFLUORESCEIN(CAS DataBase Reference)
• NIST Chemistry Reference: NAPHTHOFLUORESCEIN(61419-02-1)
• EPA Substance Registry System: NAPHTHOFLUORESCEIN(61419-02-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8-10
• Hazardous Substances Data: 61419-02-1(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
NAPHTHOFLUORESCEIN is used as a pH-sensitive fluorescent probe for monitoring changes in pH levels in various experimental setups. Its color change in response to pH variations allows researchers to study the behavior of molecules and cellular processes under different conditions.
Used in Label Preparation:
NAPHTHOFLUORESCEIN is used as a component in the preparation of labels for various purposes. Its fluorescent properties make it an ideal choice for creating labels that can be easily detected and tracked, particularly in biological and chemical applications.
Used in Enzyme Substrates:
NAPHTHOFLUORESCEIN is used as a substrate for enzymes that can cleave the molecule and release the fluorescent component. This allows researchers to study enzyme activity and kinetics, as well as to develop assays for detecting specific enzymes.
Used in Pharmaceutical Industry:
NAPHTHOFLUORESCEIN is used as a furin inhibitor in the pharmaceutical industry. Furin is a protease enzyme involved in the processing of proteins, and its inhibition can have therapeutic applications in various diseases. By using NAPHTHOFLUORESCEIN as a furin inhibitor, researchers can study the effects of inhibiting furin activity and develop potential treatments for related conditions.

InChI:InChI=1/C28H16O5/c29-17-7-9-19-15(13-17)5-11-23-25(19)32-26-20-10-8-18(30)14-16(20)6-12-24(26)28(23)22-4-2-1-3-21(22)27(31)33-28/h1-14,29-30H

Upstream product

• 100884-30-8 1,6-bis-methoxymethoxy-naphthalene 
• 575-44-0 1,6-dihydroxynaphthalene 
• 85-44-9 phthalic anhydride 
• 7664-93-9 sulfuric acid 
• 397883-28-2 2-(1.6-dihydroxy-[2]naphthoyl)-benzoic acid 

Downstream Products

• 77084-71-0 3,11-diacetoxy-spiro[dibenzo[c,h]xanthene-7,1'-phthalan]-3'-one 
• 77084-72-1 3,11-bis-benzoyloxy-spiro[dibenzo[c,h]xanthene-7,1'-phthalan]-3'-one 
• 1380077-15-5 methyl 2-(11-hydroxy-3-oxo-3H-dibenzo[c,h]xanthen-7-yl)benzoate 
• 51517-45-4 3,11-dihydroxy-3′H-spiro[dibenzo[c,h]xanthene-7,1′-isobenzofuran]-3′-one 
• 874657-97-3 C₄₂H₂₈O₉S₂ 

Relevant articles and documents

A dual-response naphthofluorescein-based fluorescent probe for multiple-channel imaging of cysteine/homocysteine in living cells

A naphthofluorescein-based fluorescent probe with two independent reaction sites (nitro-2,1,3-benzoxadiazole and acrylate moiety) was developed. Integrating these two reaction sites into a single molecule not only can guarantee the selective detection of Cys/Hcy in an elegant fashion, but also can enable Cys/Hcy detection in a multiple-channel responsive manner.

A water-soluble near-infrared fluorescent probe for specific Pd2+ detection

Palladium (Pd) is widely used in chemistry, biology, environmental science etc., and Pd2+ is the most plenitudinous oxidation state of the Pd that can exist under physiological conditions or in living cells, which could have adverse effects on both our health and environment. Thus, it is of great significance to monitor the changes of Pd2+. Hence, a novel near-infrared fluorescent probe M-PD has been developed for selective detection of Pd2+ based on naphthofluorescein in this work. The result demonstrated that M-PD exhibited favorable properties for sensing Pd2+ such as excellent water solubility, high selectivity and sensitivity. And the limit of detection was estimated as 10.8 nM, much lower than the threshold in drugs (5–10 ppm) specified by European Directorate for the Quality Control of Medicines. More importantly, detection and recovery experiments of Pd2+ in aspirin aqoeous solution and soil are satisfactory. In addition, M-PD has also been successfully used for near-infrared fluorescence imaging of Pd2+ in living cells, indicating that the probe has better feasibility and application potential in the determination of Pd2+.

METHOD FOR PRODUCING FLUORESCEIN COMPOUND

To provide a method for producing a high-purity fluorescein compound on an industrial scale efficiently and safely.SOLUTION: A compound having a phenolic hydroxyl group and an acid anhydride are reacted with each other in the presence of an acidic catalyst, to obtain a fluorescein compound. The resultant fluorescein compound is dissolved in an alkaline solvent and then an acid is added thereto, controlling the pH of the solution into the acidic region. After that, an inorganic salt is added thereto, forming crystals. In this way, a fluorescein compound is produced.SELECTED DRAWING: Figure 1

HIGH-PURITY FLUORESCEIN COMPOUND AND MANUFACTURING METHOD THEREOF

PROBLEM TO BE SOLVED: To provide a high-purity fluorescein compound, and to provide a method for producing a high-purity fluorescein compound in an efficient and a highly safe manner on an industrial scale. SOLUTION: A compound having a phenolic hydroxy group and an acid anhydride compound are reacted with a solvent containing a carboxylic acid as a reaction solvent in the presence of an acidic catalyst to obtain a highly pure fluorescein compound represented by formula (1) having a chemical purity of 95% or more. In the formula (1), x, y, and z represent an integer of 0 to 4, and R1, R2, and R3 each independently represents a fused benzene ring having a substituent or an unsubstituted fused benzene ring. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Synthesis and optical properties of L-shaped dinaphthofluoresceins with two peripheral hydroxy groups

The four compounds 6 and 8-10 having the same L-shaped dinaphthofluorescein skeleton were constructed. The only structural differences among these four compounds were the positions of the two peripheral hydroxy groups. Their dianion forms are a resonance system, thus 6 and 8-10 were expected to exhibit similar optical properties such as the maximum absorption wavelength, molar absorptivity, maximum emission wavelength and fluorescence quantum yield. However, 6 and 8-10 showed quite different optical properties. For example, the maximum absorption wavelengths of 6, 8, 9 and 10 in aqueous pH 11 solution were 650 nm, 733 nm, 558 nm and 746 nm, respectively. Thus, the positions of the two peripheral hydroxy groups on the same skeleton significantly affected the optical properties.

Near-infrared fluorescent dyes with large stokes shifts

Embodiments of near-infrared (NIR) dyes are disclosed, along with methods and kits for detecting analytes with the NIR dyes. The NIR dyes have a structure according to the general structure At least one of R1/R2, R2/R3, R3/R4, R5/R6, R6/R7, and/or R7/R8 together forms a substituted or unsubstituted cycloalkyl or aryl.

Strong red fluorescent probes suitable for detecting hydrogen peroxide generated by mice peritoneal macrophages

This paper reports the synthesis, fluorescence properties, and biological applications of naphthofluorescein disulfonate (NFDS-1), as a red fluorescence imaging probe to detect intracellular H2O2. The Royal Society of Chemistry 2005.