934-00-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxycatechol is used as a precursor in the synthesis of polyphenolic deoxybenzoins, which are compounds with potential applications as antioxidants and tyrosinase inhibitors. Antioxidants are essential in the pharmaceutical industry to protect against oxidative stress and prevent cell damage, while tyrosinase inhibitors can be used to treat conditions related to excessive melanin production, such as hyperpigmentation.
Used in Cosmetic Industry:
In the cosmetic industry, 3-Methoxycatechol and its derived polyphenolic deoxybenzoins can be utilized as active ingredients in skincare products. Their antioxidant properties can help protect the skin from environmental stressors and premature aging, while their tyrosinase inhibitory activity can assist in reducing the appearance of age spots, sunspots, and other pigmentation issues.
Used in Food and Beverage Industry:
3-Methoxycatechol and its derivatives can also find applications in the food and beverage industry as natural antioxidants. They can be incorporated into various products to extend shelf life, maintain freshness, and protect against the negative effects of oxidation, such as rancidity and color changes.
Used in Agricultural Industry:
In agriculture, 3-Methoxycatechol and its derived compounds can be employed as natural antioxidants to improve the quality and preservation of crops, reducing post-harvest losses and maintaining the nutritional value of the produce. Additionally, their tyrosinase inhibitory properties can be utilized in the development of novel plant protection products to control enzymatic browning in harvested fruits and vegetables.

InChI:InChI=1/C7H8O3/c1-10-6-4-2-3-5(8)7(6)9/h2-4,8-9H,1H3

Upstream product

• 3934-84-7 3,4-dihydroxy-5-methoxybenzoic acid 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 87-66-1 2-hydroxyresorcinol 
• 74-88-4 methyl iodide 
• 1817-95-4 4-methoxy-benzo[1,3]dioxole 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 624-92-0 Dimethyldisulphide 
• 634-36-6 1,2,3-trimethoxybenzene 
• 60855-15-4 3-methoxy-[1,2]benzoquinone 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 7722-84-1 dihydrogen peroxide 
• 25245-37-8 1-iodo-2,3,4-trimethoxy-benzene 
• 10385-36-1 2,3,4-trimethoxybromobenzene 

Downstream Products

• 1817-95-4 4-methoxy-benzo[1,3]dioxole 
• 708-53-2 2,3-dihydroxy-4-methoxyacetophenone 
• 2876-17-7 1-methoxyphenazine 
• 60855-15-4 3-methoxy-[1,2]benzoquinone 
• 4055-69-0 2,3-dihydroxy-4-methoxybenzaldehyde 
• 30839-37-3 3,8-Dimethoxy-[1,2]naphthochinon 
• 111211-64-4 3-methoxycatechol diacetate 
• 71186-63-5 2-allyloxy-3-methoxy-phenol 
• 51066-05-8 2-(allyloxy)-6-methoxyphenol 
• 268230-66-6 3,4-dichloro-6-methoxy-pyrocatechol 
• 99548-75-1 (2,3-dihydroxy-4-methoxy-phenyl)-glyoxylic acid 
• 57580-43-5 3-Methoxy-1,2-phenylendioxydiacetonitril 
• 96217-67-3 4-methoxy-2-phenyl-benzo[1,3,2]dioxaborole 
• 82964-29-2 2'-(difluoroboryloxy)-3'-hydroxy-4'-methoxychalcone 

Relevant academic research and scientific papers

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Oxygen-Free Regioselective Biocatalytic Demethylation of Methyl-phenyl Ethers via Methyltransfer Employing Veratrol- O-demethylase

The cleavage of aryl methyl ethers is a common reaction in chemistry requiring rather harsh conditions; consequently, it is prone to undesired reactions and lacks regioselectivity. Nevertheless, O-demethylation of aryl methyl ethers is a tool to valorize natural and pharmaceutical compounds by deprotecting reactive hydroxyl moieties. Various oxidative enzymes are known to catalyze this reaction at the expense of molecular oxygen, which may lead in the case of phenols/catechols to undesired side reactions (e.g., oxidation, polymerization). Here an oxygen-independent demethylation via methyl transfer is presented employing a cobalamin-dependent veratrol-O-demethylase (vdmB). The biocatalytic demethylation transforms a variety of aryl methyl ethers with two functional methoxy moieties either in 1,2-position or in 1,3-position. Biocatalytic reactions enabled, for instance, the regioselective monodemethylation of substituted 3,4-dimethoxy phenol as well as the monodemethylation of 1,3,5-trimethoxybenzene. The methyltransferase vdmB was also successfully applied for the regioselective demethylation of natural compounds such as papaverine and rac-yatein. The approach presented here represents an alternative to chemical and enzymatic demethylation concepts and allows performing regioselective demethylation in the absence of oxygen under mild conditions, representing a valuable extension of the synthetic repertoire to modify pharmaceuticals and diversify natural products.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

Biocatalytic Methyl Ether Cleavage: Characterization of the Corrinoid-Dependent Methyl Transfer System from Desulfitobacterium hafniense

The ether functionality represents a very common motif in organic chemistry and especially the methyl ether is commonly found in natural products. Its formation and cleavage can be achieved via countless chemical procedures. Nevertheless, since in particular the cleavage often involves harsh reaction conditions, milder alternatives are highly demanded. Very recently, we have reported on a biocatalytic shuttle catalysis concept for reversible cleavage and formation of phenolic O-methyl ethers employing a corrinoid-dependent methyl transferase system from the anaerobic organism Desulfitobacterium hafniense. Here we report the technical study of this system, focusing on the demethylation of guaiacol as model reaction. The optimal buffer-, pH-, temperature- and cofactor-preferences were determined as well as the influence of organic co-solvents. Beside methyl cobalamin also hydroxocobalamin turned out to be a suitable cofactor species, although the latter required activation. Various O-methyl phenyl ethers were successfully demethylated with conversions up to 82% at 10 mM substrate concentration. (Figure presented.).

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

Synthesis and antichlamydial activity of novel phenazines

Background: Chlamydiae are widespread Gram-negative bacteria that cause a number of human diseases. Chlamydia trachomatis is the most prevalent sexually transmitted bacterial pathogen. Methods: Fourteen novel phenazine derivatives were efficiently synthesized via Buchwald-Hartwig cross coupling reaction and Suzuki reaction from 4-bromo-1-methoxyphenazine. All the derivatives displayed antichlamydial activity with IC50 values from 1.01-19.77 μM against Chlamydia trachomatis D and L2 for inhibiting progeny formation. Results: C-4 morpholinyl 8a and C-4 phenyl phenazine 9c exhibited stronger antichlamydial activity with no apparent cytotoxicity. Both phenazine derivatives inhibited chlamydial inclusions formation and growth in a dose-dependent manner. They inhibited Chlamydia infection by reducing elementary body infectivity and disturbing Chlamydia growth at the mid-stage of the chlamydial developmental cycle. Conclusion: Our findings suggest C-4 aryl and C-4 amino phenazine derivatives as promising lead molecules for antichlamydials development.

Ether bond cracking method of phenylalkyl ether

The invention discloses an ether bond cracking method of phenylalkyl ether. The method comprises the following steps: performing ether bond breaking reaction on phenylalkyl ether at -20 to reflux temperature in the presence of aluminium triiodide and dimethyl sulfoxide, thereby generating phenol and derivatives thereof. The method disclosed by the invention is mild in condition, simple and convenient for operation, high in yield, and extensive in applicable phenylalkyl ether range.

Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones

Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studies, of anilines and phenols, at the active site of toluene dioxygenase. Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives. (Figure presented.).

Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides

A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.

H2O2 in WEB: a highly efficient catalyst system for the Dakin reaction

Without using any transition metal catalyst, ligand, base, toxic or hazardous reagent, additives/promoters and organic solvent, green Dakin reactions have been successfully carried out by using H2O2 in a natural feedstock extract. The reaction proceeds in neat 'Water Extract of Banana' (WEB) at room temperature under aerobic conditions in very short reaction times and, therefore, it is an evergreen and environmentally sound alternative to the existing protocols for the Dakin reaction. In our system, the reaction was found to afford excellent yield for the desired product with different electron-withdrawing and electron-donating hydroxylated benzaldehydes.