894-93-9

Usage

Uses

Used in Industrial Applications:
Sudan I is used as a coloring agent in the industrial sector for [application reason] to provide vibrant red-orange hues to plastics, oils, and waxes. Its strong coloring properties make it a popular choice for enhancing the appearance of these materials.
Used in Food Industry (with caution and restrictions):
Sudan I has been used in the past as a coloring agent in food products to enhance their appearance with a red-orange color. However, due to its potential carcinogenic properties and the risk of allergic reactions, it has been banned in many countries for use in food products. It is crucial to avoid exposure to Sudan I in food items to ensure consumer safety.
Health and Safety Considerations:
Given the potential health risks associated with Sudan I, including its carcinogenic nature and the possibility of causing allergic reactions, it is imperative to exercise caution and avoid exposure to this dye. This includes strict adherence to regulations banning its use in food products and taking necessary precautions in industrial settings to minimize ingestion or inhalation.

InChI:InChI=1/C17H13NO2/c19-16-10-9-12-5-1-2-6-13(12)14(16)11-18-15-7-3-4-8-17(15)20/h1-11,18,20H/b14-11+

Upstream product

• 148642-24-4 1-((pyrimidine-2-ylimino)methyl)naphthalene-2-ol 
• 95-55-6 2-amino-phenol 
• 135-19-3 β-naphthol 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 

Downstream Products

• 98348-91-5 UO₂⁽²⁺⁾*C₁₇H₁₁NO₂^(2-)=UO₂(C₁₇H₁₁NO₂) 

Relevant academic research and scientific papers

Synthesis, spectroscopic characterization and in vitro studies of new heteroleptic copper (II) complexes derived from 2-hydroxy napthaldehyde Schiff's bases and N, N donor ligands: Antimicrobial, DNA binding and cytotoxic investigations

A series of eight new copper (II) complexes of types [Cu(HL1)(B)] (4a-4d) and [Cu(HL2)(B)] (4e-4h), where HL1 is N-(2-hydroxy-1-naphthalidene)-2-aminophenol, HL2 is N-(2-hydroxy-1-naphthylidene)-2-mercaptoaniline and B is N, N donor ligands viz bipyridyl (bpy), 1,10-phenanthroline (phen), dipyridoquinoxaline (dpq) and dipyridophenazine (dppz) have been synthesized and characterized by elemental analysis as well as by spectroscopic techniques (IR, UV, ESI mass and EPR spectra). The DNA-binding properties of these copper complexes (4a-4h) have been investigated by electronic absorption, viscosity measurements and docking analyses. The results obtained indicated that the complexes get bonded with DNA via an intercalation binding mode with an intrinsic binding constant, Kb (1.116 ± 0.21 to 7.227 ± 0.21) × 104 M-1. The antimicrobial activity assays with the Schiff's bases and their heteroleptic copper (II) complexes of 4a and 4b exhibited profound activity against gram positive bacteria, gram negative bacteria and fungi. Further, complexes 4d and 4h displayed significant cytotoxicity when examined in vitro on a panel of cancerous cell line - human liver cancer cell line - HepG-2 cells (IC50 = 40.82 and 29.74 μg/ml).

UV–vis spectral property of a multi-hydroxyl Schiff-base derivative and its colorimetric response to some special metal ions

A multi-hydroxyl Schiff-base derivative, N-2′-hydroxyl-1′-naphthyl methylene-2-amino phenol (HNMAP), was synthesized and characterized by FTIR, 1H NMR and UV–vis spectroscopy. It was noted to find there was great effect for solvent and pH on the UV–vis spectroscopy of HNMAP. Especially, some metal ions could make its UV–vis spectra changed regularly with different time-resolved effects. For example, a real-time and multi-wavelength response to Fe2+ at 520 nm, 466 nm and 447 nm and a quite slow one about 26 min to Fe3+ at 447 nm and 466 nm, respectively. Under the optimized conditions, the changes in the corresponding absorption intensities at above wavelengths were in proportion to cFe 2+ or cFe 3+ during respectively partitioned linear ranges, which realized to quantitatively detect Fe2+ or Fe3+ with a large linear range more than two orders of magnitude. A 1:1 complex mode for HNMAP-Fe2+ and 1:2 for HNMAP-Fe3+ were proposed from UV–vis spectral titration and Job's plot. HNMAP would be a potential sensor for colorimetric detection of Fe2+ and Fe3+ in practice.

Three novel Ni(II), VO(II) and Cr(III) mononuclear complexes encompassing potentially tridentate imine ligand: Synthesis, structural characterization, DNA interaction, antimicrobial evaluation and anticancer activity

Three novel Cr(III),VO(II) and Ni(II) imine complexes derived from the condensation of 2-aminophenol (AP) with 2-hydroxynaphthaldehyde (HN) were synthesized. The prepared HNAP imine ligand and its complexes were investigated via various physicochemical tools. The results suggest that the parent ligand behaves as a dibasic tridentate ONO ligand, when coordinated to Cr(III) in octahedral and to Ni(II) in tetrahedral geometry. In the case of VO(II), it coordinates in distorted square pyramidal geometry. Also, the prepared compounds were screened for their antimicrobial activities against pathogenic bacteria, Escherichia coli (?ve), Bacillus subtilis (+ve) and Staphylococcus aureus (+ve), and some types of fungi, Aspergillus niger, Candida glabrata and Trichophyton rubrum. The results indicate that the complexes show a stronger antimicrobial efficiency compared to the pro-ligand. The interaction of the prepared complexes with calf thymus DNA was investigated using spectral, viscosity and gel electrophoresis measurements. The obtained results clearly demonstrate that the binding affinity with calf thymus DNA follows the order HNAPCr > HNAPV > HNAPNi. The cytotoxic activity of the prepared compounds on human colon carcinoma cells (HCT-116 cell line), hepatic cellular carcinoma cells (HepG-2cell line) and breast carcinoma cells (MCF-7cell line) was examined. From these results it is found that the investigated complexes have potent cytotoxicity against growth of carcinoma cells compared to the corresponding imine pro-ligand.

π-Conjugated molecules identified for reversible and visual detection of F? in aqueous: Effect of heterocycle unit on sensing performance

To illustrate the impact of molecular structure, especially heterocycle unit, on the sensing performance, two kinds of π-conjugated molecules containing aromatic heterocyclic (Dye 1) and aromatic ring (Dye 2) were identified and compared each other. Even with similar structures, they possessed quite different spectral and colorimetric responses to F?, Cl?, Br?, I?, NO3 ?, HSO4 ?, H2PO4 ?, ClO4 ? and CH3COO?, etc. The reason might result from the difference in withdraw-electron ability of aromatic and heterocyclic rings, which would lead to different acidity of active H in the target π-conjugated molecules. In acidic aqueous, Dye 1 expressed a reversible ratiometric-colorimetric response to F?, accompanying with a visual color change from bright yellow to purple, a nice linear range of 2.0–35.0 × 10?6 mol/L and a low detection limit of 1.60 × 10?7 mol/L. While Dye 2 did not react with any anion due to its weak acidity of active hydrogen. Under the optimized conditions, Dye 1 was successfully applied for colorimetric or naked-eye detection of F? in environmental water, tea and toothpaste samples with RSD ≤ 3.1%. The recognition mechanism for Dye 1 to F? was confirmed to be deprotonation one with a 1:1 binding stoichiometry.

Spectroscopic and computational study of a naphthalene derivative as colorimetric and fluorescent sensor for bioactive anions

The anion recognition property of a naphthalene based receptor (L) was investigated by naked-eye, UV-Vis, fluorescence, 1H NMR and computational methods. The receptor L showed fluoride selective naked-eye detectable colorimetric and UV-Vis spectral changes over other tested anions due to the formation of hydrogen bonding complex in 1:1 stoichiometry and/or deprotonation between fluoride and the receptor. Interestingly, the fluorescence of L was quenched by fluoride but enhanced by acetate.

A "turn-on" fluorescent chemosensor for aluminum ion and cell imaging application

A simple and efficient fluorescent chemosensor for Al3 + is reported in the paper. The chemosensor is obtained by dehydration reaction of 2-hydroxy-1-naphthaldehyde and 2-aminophenol. The chemosensor has high selectivity and sensitivity for Al3 + and displays fluorescence "off-on" switch signal. The detection limit of the chemosensor for Al3 + can reach 1.0 × 10- 7 M in DMSO/H2O (1:9, v/v) solution. The mass spectra and Job's plot analysis confirm the 1:1 stoichiometry between chemosensor and Al3 +. Potential utilization of the probe as an intracellular sensor of Al3 + in human cancer (HiSa) cells is also examined by confocal fluorescence microscopy.

The arginine detection and cytotoxicity of fluorescent probes based on naphthalene derivatives

From a biological point of view, Schiff base probes containing fluorescent groups are chemically modified to provide an effective method for the detection of amino acids. According to this method, three molecular probes containing Schiff base and hydroxyl group have been designed and synthesized. UV-Vis and fluorescent data indicated that compound 2 showed strong sensitivity and high selectivity for arginine (Arg) among normal twenty kinds of amino acids. In addition, compound 2 displayed high combining ability with Arg and low cytotoxicity in MCF-7 cell from 0 to 150?μg/mL. The above results showed the synthesized probes also can be used a biosensor for the Arg detection in vivo.

Synthesis, characterization, DFT study and antioxidant activity of (2-hydroxynaphthalen-1-yl) methyl 2-hydroxyphenyl amino phosphonic acid

New molecule α-aminophosphonate namely (2-hydroxynaphthalen-1-yl) methyl 2-hydroxyphenyl amino phosphonic acid (HMHP) was synthesized by condensation based on 2-amino phenol and 2-hydroxy naphthaldehyde. During the reaction, imine intermediate namely 2-hydroxyphenyl imino naphthalen-2-ol (HIN) was formed before adding acid phosphorous to the reaction mixture. It can be confirmed the concept of Kabachinik-Fields reaction, which it's perform the attachment of phosphorus atom to the carbon atom of imine function. Both compounds were identified using IR, 1H, 13C and 31P NMR spectroscopic techniques. The evaluation of the antioxidant activity of HMHP and HIN was investigated by utilizing several in vitro assays: scavenging activity against DPPH radical and H2O2 non radical, β-carotene/linoleic acid against linoleic peroxidation, reducing power against ferric oxidation and phosphomolybdate (TAC) against molybdate ion oxidation. Results indicate that HMHP reflects greater antioxidant potency compared to HIN in most tests, where it is apt to offer the hydrogen radical very well at IC50 (37.64 ± 1.43) in DPPH test. For the other tests the inhibition percent at 50 % are relatively closed between them. Except the H2O2 scavenging, while HIN exhibited excellent activity at IC50 (24.7306 ± 0.71785). The quantum chemical calculations were performed using density functional theory (DFT) to study the effects of the transfer electronic and proton transfer on the antioxidant activities of the synthesized compounds. Also, theoretical FT-IR was calculated. The experimental results are in comfort with those calculated theoretically.

Reinforcement of ‘imine-hydroxyl chelation pocket’ by encapsulating into the β-CD cavity for the sterically protective detection of Al3+

The effect of encapsulating a schiff base probe; o-phenolnaphthylimine (pni) into β-cyclodextrin (β-CD) and its impact on the detection of Al3+ was investigated using the spectrofluorometric technique. The impact of imine moiety and the neighbouring hydroxyl groups of pni in the sensing of Al3+ were assessed through the experimental and computational procedure. The role of ‘imine-hydroxyl chelation pocket’ of pni in the detection of Al3+ was estimated, correlated and demonstrated. FTIR, NMR and mass spectral techniques were used for the investigations in solid state. Stoichiometry of the complexes was estimated using UV–visible and fluorescence spectral techniques in liquids state. Molecular modeling and steric maps were obtained using 3D structural data of compounds. Linearity range, LOD and LOQ were estimated from the selectivity and sensitivity studies. The proposed work demonstrates the impact of additional binding centers that has to be considered while designing a chemosensor for metal cations.

Condensation product of 2-hydroxy-1-napthaldehyde and 2-aminophenol: Selective fluorescent sensor for Al3+ ion and fabrication of paper strip sensor for Al3+ ion

The condensation product of 2-hydroxy-1-napthaldehyde and 2-aminophenol (L), in 1:1 (v/v) CH3OH:H2O acts as selective fluorescent sensor for Al3+. The fluorescence intensity of L at emission wavelength 517 nm, when excited with 360 nm photons, increases on interaction with Al3+ by ca. 7-fold. Under UV lamp, L shows light yellow fluorescence on interaction with Al3+ visible to bare eyes. Metal ions – Na+, K+, Ca2+, Mg2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, Pb2+, Cd2+ and Hg2+do not interfere. The increase in fluorescence intensity is due to the quenching of photoinduced electron transfer (PET) process prevailing in L. The fluorescent and UV/Visible spectral data analysis showed a 1:1 complexation between L and Al3+ with logβ = 4.532 (β = binding constant) and detection limit 10?5 M. DFT and TDDFT calculations also confirm 1:1 interaction between L and Al3+. L has been successfully applied in fluorescent imaging of Al3+ in live rat L6 myoblasts cells and as paper strip fluorescent sensor for Al3+ in aqueous medium.