6342-70-7

Usage

Uses

Used in Fragrance and Flavor Industry:
Methyl 3-methoxysalicylate is used as a fragrance ingredient for its sweet, floral scent, contributing to the pleasant aroma of personal care products such as perfumes, lotions, and shampoos.
Used in Food Industry:
As a flavoring agent, Methyl 3-methoxysalicylate enhances the taste and aroma of food products, providing a unique and appealing flavor profile.
Used in Industrial and Household Products:
Methyl 3-methoxysalicylate is used as an additive in a range of industrial and household products to impart a pleasant scent and improve the overall sensory experience of these products.
Synthesis:
Methyl 3-methoxysalicylate is synthesized through the esterification of 3-methoxysalicylic acid with methanol, a process that highlights its chemical versatility and potential for use in various applications.

InChI:InChI=1/C9H10O4/c1-12-7-5-3-4-6(8(7)10)9(11)13-2/h3-5,10H,1-2H3

Upstream product

• 67-56-1 methanol 
• 877-22-5 3-methoxysalicylic acid 
• 2150-42-7 methyl 2,3-dimethoxybenzoate 
• 74-88-4 methyl iodide 
• 102-52-3 malonaldehydebis(dimethylacetal) 
• 107953-75-3 1,4-dimethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene 
• 196601-61-3 2-benzenesulfonyloxy-3-methoxy-benzoic acid 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 2426-85-9 2-Hydroxy-3-methoxybenzaldehyde benzenesulfonate 
• 186581-53-3 diazomethane 
• 5368-81-0 methyl 3-methoxybenzoate 

Downstream Products

• 134419-43-5 5-bromo-2-hydroxy-3-methoxy-benzoic acid methyl ester 
• 134419-45-7 2-methoxy-6-methoxycarbonyl-4-nitrophenol 
• 500798-31-2 2-acetoxy-3-methoxy-benzoic acid methyl ester 
• 96619-89-5 3-methoxy-2-(2-propenyloxy)benzoic acid, methyl ester 
• 132338-45-5 methyl 3-methoxyl-2-(trifluoromethylsulfonyloxy)benzoate 
• 134419-46-8 methyl 5-chloro-3-methoxysalicylate 
• 134419-44-6 methyl 5-iodo-3-methoxysalicylate 
• 101093-92-9 2-Phenoxy-3-methoxy-benzoesaeure-methylester 
• 157187-05-8 2-dimethylthiocarbamoyloxy-3-methoxybenzoic acid methyl ester 
• 278175-50-1 methyl 3-methoxy-2-(perfluoro-1-butanesulfonyloxy)benzoate 
• 688745-54-2 1-(2-hydroxy-3-methoxyphenyl)-3-morpholin-4-yl-3-oxopropan-1-one 
• 99179-82-5 2,5-dihydroxy-3-methoxy-benzoic acid methyl ester 
• 6702-58-5 4-methoxy-9H-xanthen-9-one 
• 133129-71-2 2,3-dimethoxy-5-propylbenzoic acid 

Relevant academic research and scientific papers

Phosphorescence at Low Temperature by External Heavy-Atom Effect in Zinc(II) Clusters

Luminescent ZnII clusters [Zn4L4(μ3-OMe)2X2] (X=SCN (1), Cl (2), Br (3)) and [Zn7L6(μ3-OMe)2(μ3-OH)4]Y2 (Y=I? (4), ClO4? (5)), HL=methyl-3-methoxysalicylate, exhibiting blue fluorescence at room temperature (λmax=416≈429 nm, Φem=0.09–0.36) have been synthesised and investigated in detail. In one case the external heavy-atom effect (EHE) arising the presence of iodide counter anions yielded phosphorescence with a long emission lifetime (λmax=520 nm, τ=95.3 ms) at 77 K. Single-crystal X-ray structural analysis and time-dependent density-functional theory (TD-DFT) calculations revealed that their emission origin was attributed to the fluorescence from the singlet ligand-centred (1LC) excited state, and the phosphorescence observed in 4 was caused by the EHE of counter anions having strong CH?I interactions.

Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors

In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.

Choleretic drug alibendol preparation method

The invention belongs to the field of drug synthesis, and provides an alibendol preparation method, which comprises: selecting 2-hydroxy-3-methoxybenzaldehyde as a raw material, selecting an efficientoxidative esterification catalyst, carrying out one-step oxidative esterification to obtain methyl 2-hydroxy-3-methoxybenzoate, carrying out a reaction on the methyl 2-hydroxy-3-methoxybenzoate and allyl bromide under the action of an alkali to generate methyl 2-allyloxy-3-methoxybenzoate, carrying out a para Claisen rearrangement reaction on the methyl 2-allyloxy-3-methoxybenzoate at a high temperature to obtain methyl 2-hydroxy-3-methoxy-5-allylbenzoate, and carrying out an aminolysis reaction in ethanolamine to generate alibendol. Compared with the traditional synthetic process, the new process of the present invention has characteristics of simple synthesis steps, convenient post-treatment and good product quality, and is suitable for industrial production.

Pharmaceutical composition for use in preventing or treating poly(ADP-ribose)polymerase-1 related diseases containing the same as an active ingredient

The present invention relates to a novel compound, a method for manufacturing the same, and a pharmaceutical composition for preventing or treating poly(ADP-ribose)polymerase-1 (PARP-1) related diseases containing the compound as an active ingredient. The novel PARP-1 inhibitory compound according to the present invention exhibits an excellent PARP-1 inhibitory effect at a concentration of nanomol unit and further exhibits an excellent cytoprotective effect (cell death inhibitory effect) on ophthalmic diseases or disorders, especially on retinal diseases. The composition containing the compound as an active ingredient is useful as a composition for preventing or treating PARP-1 related diseases, for example, ophthalmic diseases or disorders.(AA) Example 37(BB) Example 39COPYRIGHT KIPO 2018

Chromatography-free, Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids to 3-hydroxybenzisoxazoles

The Mitsunobu reaction has become one of the most powerful tools to alkylate acidic pronucleophiles. A significant caveat of Mitsunobu chemistry, however, is that the reaction mixture is often plagued with purification problems owing to the phosphine oxide and hydrazine dicarboxylate by-products. In addition to the development of more readily separable Mitsunobu reagents, the product's physicochemical properties may be exploited to facilitate purification. In this regard, we present a swift and efficient preparation of 3-hydroxybenzisoxazoles by the Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids, which can be isolated by an acid–base work-up. As expected, a range of functional groups was compatible with the chemistry.

Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide

The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Expeditious synthesis of benzopyrans via lewis acid-catalyzed C-H functionalization: Remarkable enhancement of reactivity by an ortho substituent

An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.

Efficient synthesis of salicylates by catalytic [3 + 3] cyclizations of 1,3-bis(silyl enol ethers) with 1,1,3,3-tetramethoxypropane

(Chemical Equation Presented) Salicylic acid derivatives were prepared by Me3SiOTf-catalyzed [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 1,1,3,3-tetramethoxypropane.

Synthesis and structure activity relationship studies of benzothieno[3,2-b]furan derivatives as a novel class of IKKβ inhibitors

As a novel class of IKKβ inhibitors, a series of tricyclic furan derivatives was designed and synthesized based on the structure of known thiophene IKKβ inhibitors. Among the various fused furan derivatives synthesized, a benzothieno[3,2-b]furan derivative 13a displayed potent inhibitory activity towards IKKβ in enzymatic and cellular assays. The potent inhibitory activity originates from an intramolecular non-bonded S...O interaction which was confirmed by the X-ray structure of JNK3 with 16k. The introduction of further substituents on the core structure led to the discovery of the 6-alkoxy derivatives, which possessed a comparable IKKβ inhibitory activity to 13a and an improved metabolic stability. Among these, appropriately lipophilic compounds 16a, h, i, and 13g (logD>2) were found to possess good oral bioavailability.