17295-12-4

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 6-HYDROXY-2-NAPHTHOATE is used as an intermediate in the synthesis of various pharmaceutical compounds for its versatile chemical properties.
Used in Fragrance Industry:
ETHYL 6-HYDROXY-2-NAPHTHOATE is used as a component in the formulation of fragrances due to its unique scent profile.
Used in Food and Beverage Industry:
ETHYL 6-HYDROXY-2-NAPHTHOATE is used as a flavoring agent in food and beverages to enhance taste and aroma.
Used in Organic Synthesis:
ETHYL 6-HYDROXY-2-NAPHTHOATE is used as a building block in the synthesis of various organic compounds due to its reactive functional groups.
Used in Material Science:
ETHYL 6-HYDROXY-2-NAPHTHOATE is used in the development of new materials with unique properties, such as antimicrobial coatings or antioxidant additives.

InChI:InChI=1/C13H12O3/c1-2-16-13(15)11-4-3-10-8-12(14)6-5-9(10)7-11/h3-8,14H,2H2,1H3

Upstream product

• 78119-76-3 6-Benzoyloxy-naphthalene-2-carboxylic acid ethyl ester 
• 78119-72-9 acetate of α,α,α',α'-tetrabromo-3,4-xylenol 
• 140-88-5 ethyl acrylate 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 78119-71-8 benzoate of α,α,α',α'-tetrabromo-3,4-xylenol 
• 64-17-5 ethanol 

Downstream Products

• 134472-57-4 6-[6-[2,3-bis(Phenylmethoxy)phenyl]hexyloxy]-2-naphthalene carboxylic acid 
• 1025460-02-9 ethyl 5-amino-6-hydroxy-2-naphthoate 
• 100-61-8 N-methylaniline 
• 849421-24-5 6-hydroxy-naphthalene-2-carboxylic acid hydrazide 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 
• 582313-92-6 6-[2-(5-benzyl-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyrrol-4-yl)ethoxy]naphthalene-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

A dual-function probe based on naphthalene for fluorescent turn-on recognition of Cu2+ and colorimetric detection of Fe3+ in neat H2O

A simple naphthalene derivative, 6-hydroxy-2-naphthohydrazide (NAH), was designed and synthesized through two facile steps reactions with the 6-hydroxy-2-naphthoic acid (NCA) as the starting material. In neat H2O (10% 0.01 M HEPES buffer, v/v, pH = 7.4), probe NAH showed a highly selective and sensitive response towards Fe3+ via perceptible color change and displayed “turn-on” dual-emission fluorescence response for Cu2+. The binding stoichiometry ratio of NAH/Cu2+ and NAH/Fe3+ were all confirmed as 1:1 by the method of fluorescence job's plot and UV–Vis job's plot, respectively. Probe NAH can be used over a wide pH range for the determination of Fe3+ (2.0–10.0) and Cu2+ (6.0–10.0) without interference from other co-existing metal ions. A possible detection mechanism was the hydrolysis of NAH upon the addition of Fe3+ or Cu2+, thereby leading to the formation of 6-hydroxy-naphthalene-2-carboxylic acid (NCA) which was further confirmed by the various spectroscopic techniques including FT-IR, 1H NMR titration and HRMS. Moreover, NAH was successfully applied to the detection of Cu2+ and Fe3+ in tap water, ultrapure water and BSA.

Experimental and quantum chemical calculations of imidazolium appended naphthalene hybrid in different biomimicking aqueous interfaces

The effect of solvent polarity and micellar headgroup on a newly designed imidazolium based ionic liquid (IL) conjugated with naphthalene, 1,2-dimethyl-3-((6-(octyloxy)naphthalen-2-yl)methyl)-1H-imidazol-3-ium chloride (IN-O8-Cl), was studied using steady state and time-resolved fluorescence techniques. We observed that the dipole moment in the excited state is remarkably higher than the ground state. The effect of micellar surface charge on the photophysics of IN-O8-Cl in aqueous phase at room temperature was investigated. Formation of premicellar aggregates in sodium dodecylsulfate (SDS) was perceived; further the microenvironment of IN-O8-Cl was examined using steady-state fluorescence spectroscopy. Micropolarity of the micellar environment of SDS was found to be lower than that of cetyltrimethylammonium bromide (CTAB) and triton X-100 (TX100) following the order SDS b) and edge excitation red shift (EERS) from the emission maximum suggest that the probe binds strongly to the micelles. Multiexponential behavior was observed in time-resolved fluorescence lifetime studies in all micellar environments. We have observed an increase in rotational correlation time as we move from pure aqueous phase to solution containing surfactants of different head charge. Varieties of spectral parameters were used to justify the region in which the probe is present. The experimentally obtained dipole moment data were justified and explained by the DFT calculations of the electronic properties of IN-O8-Cl molecules in gas phase and in selected solvents.

Synthesis and physico-chemical properties of polar liquid crystal materials incorporating a coumarin skeleton at the terminal position

This paper described the synthesis and physico-chemical properties of homologous series of 2-oxo-2H-chromen-6-yl 6-alkoxy-naphthalene-2-carboxylate (compounds 1-n). Compounds 1-n show a monotropic nematic (N) phase, where the average of the N-isotropic (I) phase transition temperatures is ca. 140C. The mesomorphic properties were also examined by binary phase diagrams for the mixture of 1-n (n=4 or 8) and 4-(cyano-4'-octyloxybiphenyl (8 OCB), or 4-heptyloxyphenyl 4-nonyloxybenzoate. The physico-chemical properties for compounds 1-n are compared with the corresponding 4-alkoxybenzoate derivatives (compounds 2-n) and 4-alkoxybiphenyl-4'-carboxylate ones (compounds 3-n). These results are discussed in terms of molecular structures and the electrostatic natures of the molecules.

Stabilization of Bicontinuous Cubic Phase and Its Two-Sided Nature Produced by Use of Siloxane Tails and Introduction of Molecular Nonsymmetry

A recent intriguing finding that a helical network arrangement forms the bicontinuous cubic phase is attracting great attention for the possibility of new routes to asymmetric synthesis by achiral molecules. However, the design of the molecular structure

Preparation method of 6-hydroxy-2-naphthoic acid

The invention provides a preparation method of 6-hydroxy-2-naphthoic acid, and particularly relates to the field of chemical processes. Herein, the ethyl 6-isopropyl-2-naphthoate is used as a raw material, isopropyl is hydroxylated through free radical reaction to prepare ethyl 6-hydroxy-2-naphthoate, and finally, the target product 6-hydroxy-2-naphthoic acid is prepared through hydrolysis and acidification. The method is mild in preparation condition, simple in equipment requirement and high in yield.

Unsymmetric 1,3,4-oxa(thia)diazoles of quinoxaline-naphthalene conjugates

Two new series of unsymmetric 1,3,4-oxa(thia)diazoles 1a,b containing both quinoxaline and naphthalene moieties were prepared and their mesomorphic properties were investigated. The mesomorphic behavior of compounds 1a,b and 2 was studied by DSC analysis

Discovering potent inhibitors against the β-hydroxyacyl-acyl carrier protein dehydratase (FabZ) of helicobacter pylori: Structure-based design, synthesis, bioassay, and crystal structure determination

The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC50 values less than 2 μM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC 50) 0.86 μM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

BENZIMIDAZOLE OR INDOLE AMIDES AS INHIBITORS OF PIN1

The invention relates to compounds of the formula (1) and to pharmaceutically acceptable salts and solvates thereof, wherein the variables are defined herein. The invention also relates to methods of treating abnormal cell growth in mammals by administering the compounds of formula (1) and to pharmaceutical compositions for treating such disorders that contain the compounds of formula (1). The invention also relates to methods of preparing the compounds of formula (1).

Design, synthesis and evaluation of carbazole derivatives as PPARα/γ dual agonists and antioxidants

A series of hydroxycarbazole derivatives were synthesized and evaluated for PPARα/γ dual agonist as well as antioxidant activities. While most compounds showed good antioxidant activity, some compounds were identified as potential PPARα/γ dual agonists as well. Compounds 10a and 16 were found to be active in animal studies.

Antagonist analogue of 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2- naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest

The retinoid 6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-2- naphthalenecarboxylic acid (AHPN) and its active analogues induce cell-cycle arrest and programmed cell death (apoptosis) in cancer cells independently of retinoic acid receptor (RAR) interaction. Its analogue, (E)-4-[3′-(1- adamantyl)-4′-hydroxyphenyl]-3-(3′-acetamidopropyloxy)cinnamic acid (3-A-AHPC) selectively antagonized cell apoptotic events (TR3/nur77/NGFI-B expression and nuclear-to-mitochondrial translocation) but not the proliferative events (cell-cycle arrest and p21WAF1/CIP1 expression) induced by proapoptotic AHPN and its analogues. The syntheses of 3-A-AHPC and proapoptotic (E)-6-[3′-(1-adamantyl)-4′-hydroxyphenyl]-5- chloronaphthalenecarboxylic acid (5-Cl-AHPN) are described. Computational studies on AHPN, AHPC, and three substituted analogues (5-Cl-AHPN, 3-Cl-AHPC, and 3-A-AHPC) suggested reasons for their diametric effects on RAR activation. Density functional theory studies indicated that the 1-adamantyl (1-Ad) groups of the AHPN and AHPC configurations assumed positions that were nearly planar with the aromatic rings of their polar termini. In contrast, in the configurations of the substituted analogues having chloro and 3-acetamidopropyloxy groups, rather than a hydrogen, ortho to the diaryl bonds, the diaryl bond torsion angles increased so that the 1-Ad groups were oriented out of this plane. Docking and molecular dynamics of AHPN, AHPC, and these substituted analogues in the RARγ ligand-binding domain illustrated how specific substituents on the AHPN and AHPC scaffolds modulated the positions and dynamics of the 1-Ad groups. As a result, the position of RARγ helix H12 in forming the coactivator-binding site was impacted in a manner consistent with the experimental effect of each analogue on RARγ transcriptional activation.