452-86-8

Usage

Uses

Used in Chemical Synthesis:
4-Methylcatechol is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional groups make it a valuable building block for the development of new molecules with potential applications in different industries.
Used in Antimicrobial Applications:
4-Methylcatechol is used as an antimicrobial agent, exhibiting broad-spectrum activity against various microorganisms, including bacteria, fungi, and viruses. Its antimicrobial properties can be attributed to its ability to disrupt cell membranes, interfere with essential cellular processes, and generate reactive oxygen species, leading to the inhibition or killing of pathogens.
Used in Antioxidant Applications:
4-Methylcatechol is used as an antioxidant, protecting cells and tissues from oxidative damage caused by reactive oxygen species. Its phenolic hydroxyl groups can scavenge free radicals, chelate metal ions, and prevent lipid peroxidation, thereby reducing oxidative stress and promoting overall health.
Used as an Inhibitor:
4-Methylcatechol acts as an effective inhibitor in various chemical and biological processes. It can be used to modulate enzyme activity, control the rate of chemical reactions, or interfere with the growth and proliferation of undesirable organisms, making it a useful tool in research and industrial applications.
Used in the Production of 4-Bromo-5-Methyl-Pyrocatechol:
4-Methylcatechol is used as a starting material in the synthesis of 4-bromo-5-methyl-pyrocatechol, a compound with potential applications in the pharmaceutical and chemical industries. The bromination and methylation of 4-methylcatechol can lead to the formation of this valuable derivative, expanding the range of applications for this versatile compound.
Used in Neuroprotection and Neuroregeneration:
4-Methylcatechol has been shown to increase brain-derived neurotrophic factor (BDNF) content and mRNA expression in cultured brain cells and in rat brain in vivo. This suggests that it may have neuroprotective and neuroregenerative properties, potentially benefiting conditions associated with neurodegeneration, such as Alzheimer's disease, Parkinson's disease, and stroke.

Purification Methods

Crystallise the catechol from *C6H6. The purity is checked by TLC. Crystallise it from high-boiling pet ether and distil it in a vacuum. [Beilstein 6 IV 5878.]

InChI:InChI=1/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3

Upstream product

• 110-86-1 pyridine 
• 26358-44-1 5-methylbenzo[d][1,3]dioxol-2-one 
• 79-21-0 peracetic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 698-27-1 4-methylsalicylaldehyde 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 119-33-5 4-methyl-2-nitrophenol 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 7244-03-3 6,6-diacetoxy-4-methyl-cyclohexa-2,4-dienone 
• 106-44-5 p-cresol 
• 110-22-5 diacetyl peroxide 
• 64-19-7 acetic acid 
• 7577-76-6 4-acetoxy-4-methyl-2,5-cyclohexanedienone 
• 95-84-1 3-amino-4-hydroxytoluene 

Downstream Products

• 2612-56-8 3,4-diethoxy-toluene 
• 7145-99-5 5-methyl-1,3-benzodioxole 
• 93-51-6 2-Methoxy-4-methylphenol 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 109103-65-3 4-methyl-5-(N-methyl-anilino)-[1,2]benzoquinone 
• 103441-68-5 4-aziridin-1-yl-5-methyl-[1,2]benzoquinone 
• 3131-54-2 4-methylbenzo-1,2-quinone 
• 56759-56-9 3,4,6-tribromo-5-methyl-pyrocatechol 
• 58032-63-6 4-methyl-2-(5-methyl-benzo[1,3,2]dioxaphosphol-2-yloxy)-phenol 
• 7039-14-7 2-chloro-5-methylbenzo[d]-1,3,2-dioxaphosphole 
• 89791-96-8 5-methyl-3-nitrobenzene-1,2-diol 
• 33963-45-0 3,4,6-trichloro-5-methylcatechol 
• 18863-72-4 4-bromo-5-methylbenzene-1,2-diol 
• 32359-70-9 3,4,6-trichloro-5-methyl-1,2-benzoquinone 

Relevant academic research and scientific papers

Epoxidation of styrenes with the peroxidase from the cultured cells of Nicotiana tabacum

An enzyme concerned with the epoxidation of styrenes was isolated from cultured cells of Nicotiana tabacum. The enzyme had peroxidase activity as well as epoxidation activity, and its amino acid sequence showed 89% homology in their 9 amino acid overlap with horseradish peroxidase. In the enzymatic reaction, hydrogen peroxide and p-cresol were necessary and molecular oxygen was the source of the oxygen atom of the epoxide. The enzymatic reaction using a spin trap reagent and monitoring of the reaction with ESR indicated that the epoxidation reaction of styrenes proceeded by a radical mechanism with peroxidase.

Hydroxylation of chlorotoluenes and cresols: a pulse radiolysis, laser flash photolysis, and product analysis study

The reactions of ·OH, O·- and SO4·- with 2-, 3-, and 4-cresols were studied by pulse radiolysis, laser flash photolysis, and product analysis techniques. The rates of OH reaction with cresols are very high (k ≈ 1 × 1010 M-1 s-1), whereas O·- was found to be less reactive (k ≈ 2.4 × 109 M-1 s-1). The second-order rate constants for SO4·- reaction with cresols are in the range (3-6) × 109 M-1 s-1. The transient absorption spectra measured in OH reaction exhibited peaks in the range 295-325 nm with a red shift for the meta isomer. The absorption spectra obtained for O·- reaction with 2-cresol has a peak at 360 nm. The absorption spectra of the transient species in SO4·- reaction obtained by pulse radiolysis and flash photolysis techniques are similar, with absorption maxima centered around 290 and 390 nm in all three isomers. The intermediates formed in ·OH, O·-, and SO4·- reactions are assigned to OH adducts, substituted benzyl radicals, and radical cations, respectively.

Selective C-C Bond Cleavage of Methylene-Linked Lignin Models and Kraft Lignin

Biorefinery and paper pulping lignins, referred hereto as technical lignins, contain condensed C-C interunit linkages. These robust C-C linkages with higher bond dissociation energies are difficult to disrupt under hydrogenolysis conditions, which are gen

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives

Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Selective ether bond breaking method of aryl alkyl ether

The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.

METHOD OF ENHANCED AROMATIC SELECTIVITY FOR GAS PHASE DEOXYGENATION OF BIO-OILS

Methods for gas-phase deoxygenation of a bio-oil are provided. In embodiments, such a method comprises exposing a bio-oil vapor comprising hydrocarbon compounds having oxygenated aromatic groups, to hydrogen gas in the presence of catalyst under conditions to induce deoxygenation of the oxygenated aromatic groups to provide a deoxygenated aromatic species, wherein the catalyst is a transition metal-incorporated mesoporous silicate having platinum deposited thereon and the transition metal is selected from Nb, W, Zr, and combinations thereof. The transition metal-incorporated mesoporous silicate catalysts are also provided.

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.