67028-40-4

Usage

Uses

Used in Flavor and Fragrance Industry:
(4-METHYLPHENOXY) ACETIC ACID ETHYL ESTER is used as a flavoring agent for its fruity, cherry, cocoa, and nut skin nuance, adding a distinct taste to various food products. Its taste threshold values make it suitable for use at low concentrations, enhancing the overall flavor profile of the products.
Used in Cosmetics and Personal Care Industry:
(4-METHYLPHENOXY) ACETIC ACID ETHYL ESTER is used as a fragrance ingredient in the cosmetics and personal care industry, providing a pleasant and long-lasting scent to products such as perfumes, lotions, and shampoos. Its unique combination of fruity, cherry, and cocoa notes contributes to a more complex and appealing fragrance.
Used in the Pharmaceutical Industry:
(4-METHYLPHENOXY) ACETIC ACID ETHYL ESTER may also find applications in the pharmaceutical industry, potentially serving as a starting material or intermediate in the synthesis of various drugs. Its unique chemical properties could be harnessed for the development of new medications or drug delivery systems.

InChI:InChI=1/C11H14O3/c1-3-13-11(12)8-14-10-6-4-9(2)5-7-10/h4-7H,3,8H2,1-2H3

Upstream product

• 940-64-7 2-(4-methylphenoxy)acetic acid 
• 106-44-5 p-cresol 
• 105-39-5 chloroacetic acid ethyl ester 
• 64-17-5 ethanol 
• 623-73-4 diazoacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 1121-70-6 sodium 4-methylphenoxide 
• 7647-01-0 hydrogenchloride 
• 105-36-2 ethyl bromoacetate 
• 75-03-6 ethyl iodide 
• 2046-82-4 Sodium; p-tolyloxy-acetate 

Downstream Products

• 1159405-66-9 N-[3-{(1H-benzo[d]imidazol-2-ylthio)methyl}-5-mercapto-4H-1,2,4-triazol-4-yl]-2-(p-tolyloxy)acetamide 
• 143999-89-7 1-Piperazin-1-yl-2-p-tolyloxy-ethanone 

Relevant academic research and scientific papers

Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl)isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents

Inflammation is the complex biological response of vascular tissues, which is partly determined by prostaglandins (PLA2). The cyclooxygenase (COX) enzyme exists in two isoforms: COX-1 and COX-2 and by the action of this, the PGs are produced. Besides, nonsteroidal anti-inflammatory drugs (NSAIDs) are therapeutic agents useful in the treatment of inflammation. Encouraged by this, the new derivatives of N'(2-phenoxyacetyl)nicotinohydrazide 9(a-e) and N'(2-phenoxyacetyl)isonicotinohydrazide 10(a-e) were designed, synthesized, characterized, and identified as remarkable anti-inflammatory and analgesic agents. These compounds were prepared in a series of steps starting with different phenol derivatives. Among the series, compound (10e) showed the highest IC50 value for COX-1 inhibition, whereas compounds (9e) and (10e) exhibited the highest COX-2SI. Further, molecular Docking Studies have been performed for the potent compound to check the three-dimensional geometrical view of the ligand binding to the targeted enzymes.

Synthesis, molecular docking and evaluation of library of 3-mercapto-1,2,4-triazole derivatives as antimicrobial agents

Due to the increasing microbial resistance to antibacterial and antifungal drugs, the development of new antimicrobial agents is an urgent priority. In search of newer antimicrobial agents, a series of 4,5-disubstituted-3-mercapto-1,2,4-triazole derivatives were synthesized from aromatic acids and substituted isothiocyanates. The in silico study was performed to study the binding interactions of the synthesized compounds with the active pocket of CYP51. Among the synthesized 3-mercapto-triazole derivatives, compounds 6r, 6s and 6u exhibited promising antimicrobial activity comparable to standard drugs. The results suggested that the structural modification to 3-mercapto-1,2,4-triazole derivatives could lead to promising antimicrobial scaffolds.

Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment

Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.

Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies

A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.

Synthesis, structural analysis, Hirshfeld surface analysis, DFT calculations, in vitro and docking study on antioxidant activity of 6-chloro-3-[(4-methylphenoxy) methyl] [1,2,4] triazolo[4,3-b]pyridazine

Pyridazine nuclei are essential elements of many natural and synthetic compounds with important biological activities. NMR and IR, as well as studies of mass spectrum, were emplyed to synthesize and characterize the title compound 6-chloro-3-[(4-methylphenoxy) methyl] [1,2,4] triazolo[4,3-b] pyridazine (CMTP). The structure of this compound was confirmed by using single crystal X-ray diffraction technique and it got crystallized in the monoclinic crystal system with the space group P2 1/c. The values of unit cell parameters are: a = 12.0965(7) ?, b = 13.6075(7) ?, c = 7.7686(4) ?, β = 93.942(3)° and Z = 4. Intermolecular hydrogen bonds of two types i.e., C-H…O and C-H…N, were noticed. Hirshfeld surface analysis was employed to account for these interaction bonds. Energy frameworks were carried out to know the dominant interaction energy involved in the molecular packing. DFT calculations were constructed to find the agreement between the theoretical and experimental values. HOMO-LUMO energy levels have been determined; global hardness, global softness, and other quantum chemical parameters have been calculated to reveal the chemical reactivity of the compound. In order to investigate the antioxidant activity of the compound, molecular docking studies were performed.

Design, modification of phyllanthone derivatives as anti-diabetic and cytotoxic agents

Twelve benzylidene derivatives, one Baeyer-Villiger oxidative, six imine derivatives were successfully designed and synthesised from phyllanthone. In the search for potential new anti-diabetic agents, phyllanthone along with its benzylidene and oxidation analogues were evaluated for enzyme inhibition against α-glucosidase. In the benzylidene series, most analogues displayed stronger activity than the mother compound. Compound 1c revealed the strongest activity, outperforming the acarbose positive control with an IC50 value of 19.59 μM. Phyllanthone and its derivatives were then tested for cytotoxic activity against the K562 cell line. The imine analogues displayed the most powerful cytotoxic activity with 3cand 3d having IC50 values of 57.55 and 68.02 μM, respectively.

Synthesis, crystal structure characterization, DFT calculations, Hirshfeld surface analysis and 3D energy frameworks of triazole pyridazine derivatives: Theoretical and experimental studies

Recently, pyridazine derivatives have shown considerable biological properties such as anti-tumor and anti-inflammatory activity. The studied compounds 6-chloro-3-[(4-methylphenoxy)methyl][1,2,4] triazolo[4,3-b]pyridazine (8a) and 6-chloro-3-[(4-fluorophenoxy)methyl][1,2,4] triazolo[4,3-b]pyridazine (8b) have been synthesized and characterized by NMR, IR and mass spectral studies, and finally, the structures were confirmed by single crystal X-ray diffraction technique. The compounds 8a and 8b have crystallized in the same crystal system with different space groups. Density functional theory calculations were performed to compare the theoretical and experimental results obtained from XRD. Further, DFT calculations were employed to determine HOMO-LUMO energy levels, energy gap, softness, hardness, and other quantum chemical parameters of the compounds 8a and 8b. Hirshfeld surface analysis was carried out to distinguish the different intermolecular hydrogen bonds. Energy frameworks for the compounds were constructed through different intermolecular interaction energies to know the dominant interaction energy involved in the molecular packing strength.

CONTROL AGENT FOR PLANT VIRUS DISEASE CONTAINING ISONICOTINIC ACID COMPOUND

PROBLEM TO BE SOLVED: To provide a novel control agent for plant virus disease containing an isonicotinic acid compound or a salt thereof. SOLUTION: A control agent for plant virus disease contains an isonicotinic acid compound having, for example the following structure, or a salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Effect of o-difluoro and p-methyl substituents on the structure, optical properties and anti-inflammatory activity of phenoxy thiazole acetamide derivatives: Theoretical and experimental studies

Thiazole derivatives (6a and 6b) have been synthesized and characterised by 1H –13C NMR, as well as LC-MS spectra. The three-dimensional structures have been confirmed by single crystal X-ray diffraction method. 6a and 6b compounds have been crystallized in the Triclinic and the Orthorhombic systems with P-1 and Pbca space groups, respectively. Supramolecular structures revealed the stability of molecules with different intermolecular interactions and different crystal packing environment. Theoretical study by Density functional theory (DFT) with B3LYP functional based on highest basis set 6–311++G(d,p) was employed to calculate the geometry and compared to the experimental data. The electronic structures and intramolecular charge transfers have been investigated by using natural population and natural bond orbital analysis (NBO). Further, DFT studies were performed to assess the frontier molecular orbitals (FMOs), energy gap, softness, hardness, and others chemical reactivity. Hirshfeld surface was investigated to distinguish the different interatomic contacts and understand the crystal packing of molecules with aid of energy frameworks through different intermolecular interaction energies based on the anisotropy of the topology. Nonlinear optical property (NLO) of the synthesized molecules were predicted by (DFT) and examined experimentally by using second harmonic generation (SHG) and revealed the importance of high NLO based on the nature of substituents and conformation. Thiazole derivatives were assessed for anti-inflammation activity by in silico molecular docking studies against COX-1 and COX-2 protein receptors revealed prominent interactions with active site and further molecular dynamics confirms the stability of the protein-ligand model. In vitro assay against cyclooxygenase (COX) enzyme gave IC50 values of 6a and 6b molecules with ortho-difluoro and para-methyl positions on benzoyl group, showed better inhibitor for COX-1 and COX-2, respectively.

Synthesis, α-glucosidase inhibition, and molecular docking studies of novel N-substituted hydrazide derivatives of atranorin as antidiabetic agents

A series of novel N-substituted hydrazide derivatives were synthesized by reacting atranorin, a compound with a natural depside structure (1), with a range of hydrazines. The natural product and 12 new analogues (2–13) were investigated for inhibition of α-glucosidase. The N-substituted hydrazide derivatives showed more potent inhibition than the original. The experimental results were confirmed by docking analysis. This study suggests that these compounds are promising molecules for diabetes therapy. Molecular dynamics simulations were carried out with compound 2 demonstrating the best docking model using Gromac during simulation up to 20 ns to explore the stability of the complex ligand-protein. Furthermore, the activity of all synthetic compounds 2–13 against a normal cell line HEK293, used for assessing their cytotoxicity, was evaluated.