496-73-1

Usage

Uses

Used in Hair Dye Industry:
4-Methylresorcinol is used as a coloring agent for its ability to produce a permanent hair color. It is often combined with other hair dye ingredients to achieve various shades, enhancing the range of color options available to consumers.
Used in Pharmaceutical Production:
4-Methylresorcinol is utilized in the production of some pharmaceuticals, leveraging its chemical properties for medicinal purposes.
Used in Organic Compound Synthesis:
In the chemical industry, 4-Methylresorcinol serves as a key component in the synthesis of other organic compounds, contributing to the development of new materials and products.

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

Upstream product

• 7577-76-6 4-acetoxy-4-methyl-2,5-cyclohexanedienone 
• 64-19-7 acetic acid 
• 108-88-3 toluene 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 38064-95-8 2,4-dimethoxy-5-methylacetophenone 
• 95-48-7 ortho-cresol 
• 7664-93-9 sulfuric acid 
• 2836-00-2 3-amino-4-methylphenol 
• 7583-20-2 2,2',4,4'-tetrahydroxydiphenylmethane 
• 121-04-0 toluene-2,4-disulfonic acid 
• 7732-18-5 water 
• 32361-58-3 2,4-dihydroxybenzenecarbodithionic acid 
• 67-56-1 methanol 
• 108-46-3 recorcinol 

Downstream Products

• 55537-31-0 2',7'-dimethylfluorescein 
• 39828-37-0 2,4-dihydroxy-5-methylbenzaldehyde 
• 71119-00-1 4-methylresorcinol diacetate 
• 93578-16-6 1-(2,4-dihydroxy-5-methylphenyl)ethan-1-one 
• 717910-36-6 1-(2,4-dihydroxy-5-methylphenyl)-2-chloroethanone 
• 52220-71-0 2,4-dihydroxy-5-methyl-benzophenone 
• 117952-43-9 1-(2,4-dihydroxy-5-methylphenyl)propan-1-one 
• 14203-46-4 4-methyl-cyclohexane-1,3-dione 
• 38064-90-3 2,4-dimethoxytoluene 
• 19217-50-6 4-methyl-3-(methyloxy)phenol 
• 20734-74-1 5-methoxy-2-methyl-phenol 

Relevant academic research and scientific papers

Natural products as sources of new fungicides (IV): Synthesis and biological evaluation of isobutyrophenone analogs as potential inhibitors of class-II fructose-1,6-bisphosphate aldolase

Several recently identified antifungal compounds share the backbone structure of acetophenones. The aim of the present study was to develop new isobutyrophenone analogs as new antifungal agents. A series of new 2,4-dihydroxy-5-methyl isobutyrophenone derivatives were prepared and characterized by 1H, 13C NMR and MS spectroscopic data. These products were evaluated for in vitro antifungal activities against seven plant fungal pathogens by the mycelial growth inhibitory rate assay. Compounds 3, 4a, 5a, 5b, 5e, 5f and 5g showed a broad-spectrum high antifungal activity. On the other hand, for the first time, these compounds were also assayed as potential inhibitors against Class II fructose-1,6-bisphosphate aldolase (Fba) from the rice blast fungus, Magnaporthe grisea. Compounds 5e and 5g were found to exhibit the inhibition constants (Ki) for 15.12 and 14.27 μM, respectively, as the strongest competitive inhibitors against Fba activity. The possible binding-modes of compounds 5e and 5g were further analyzed by molecular docking algorithms. The results strongly suggested that compound 5g could be a promising lead for the discovery of new fungicides via targeting Class II Fba.

Synthesis of sorbicillinoid analogues with anti-inflammation activities

Recently, we demonstrated potential anti-inflammatory effects of sorbicillinoids isolated from marine fungi. Here, we report the synthesis of a series of new sorbicillinoid analogues and assessed their anti-inflammatory activities. Our results reveal that side chain substitution with (E)-2-butenoyl, (E)-3-(4-fluorophenyl)-2-propenoyl, and (E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl significantly enhanced the inhibitory effects of the derivatives on nitric oxide (NO) production and inducible NO synthesis (iNOS) expression stimulated by lipopolysaccharides (LPS) in mouse macrophage. Further chemical derivatization shows that the monomethylresorcinol skeleton worked better than the dimethylresorcinol skeleton in inhibiting LPS-induced inflammatory response in cultured cells. Among the 29 synthesized sorbicillinoid analogues, compounds 4b and 12b exhibited the strongest anti-inflammatory activities, holding the promise of being developed into lead compounds that can be explored as potent anti-inflammation agents.

Method for synthesizing M-hydroxyanisole

The invention provides a method for synthesizing M-hydroxyanisole. Belong to organic synthesis technical field. The synthesis method comprises the following steps: a vapor phase mixture of resorcinol and methanol is subjected to alkylation reaction through a metal phosphate - alumina fixed phase catalyst to obtain m-hydroxyanisole. The method adopts the gas-solid phase alkylation method to synthesize the M-hydroxyanisole without separating the reaction product from the catalyst, has the characteristic of continuous reaction, and can realize continuous production in the industrial production process. The method utilizes the acid-base catalytic activity center on the surface of the stationary phase catalyst to catalyze the reaction of resorcinol and methanol, and has high resorcinol conversion rate. The method has the advantage of high selectivity of m-hydroxyanisole. Methanol is used as a methylation reagent, and the method is environmentally friendly, low in cost and high in economic benefit.

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Method for simultaneously preparing 2-methyl resorcinol and 4-methyl resorcinol

The invention provides a method for simultaneously preparing 2-methyl resorcinol and 4-methyl resorcinol, and belongs to the technical field of organic synthesis. The method comprises the following steps: resorcinol and methanol are subjected to an alkylation reaction through a metal phosphate stationary phase catalyst, and 2-methyl resorcinol and 4-methyl resorcinol are obtained. According to the method, the metal phosphate is used as the catalyst, the 2-methyl resorcinol and the 4-methyl resorcinol can be obtained at the same time by controlling the type of the catalyst, the resorcinol conversion rate is high, the joint selectivity of the 2-methyl resorcinol and the 4-methyl resorcinol can reach 60% at most, the selectivity of other products, namely intermediate hydroxyanisole is about 30%, the selectivity of m-xylylene dimethyl ether is about 5%, and the obtained products are all important intermediates for fine chemical engineering, organic chemistry and drug synthesis and are high in economic benefit. Meanwhile, methanol is used as a methylation reagent, so that the method is environment-friendly and low in price, and the production cost is reduced.

SUBSTITUTED-N-HETEROARYL COMPOUNDS AND USES THEREOF

The present disclosure relates generally to compounds useful for the treatment and/or enhancement of cognitive function and negative symptoms associated with central nervous system disorders where the circuitry involving fast spiking PV+ interneurons and the production of cortical gamma oscillations is disrupted. The subject disclosure enables the manufacture of medicaments as well as compositions containing same for use in methods of therapy and prophylaxis of cognitive dysfunction and negative symptoms.

Exploring efficacy of natural-derived acetylphenol scaffold inhibitors for α-glucosidase: Synthesis, in vitro and in vivo biochemical studies

The discovery of novel α-glucosidase inhibitors and anti-diabetic candidates from natural or natural-derived products represents an attractive therapeutic option. Here, a collection of acetylphenol analogues derived from paeonol and acetophenone were synthesized and evaluated for their α-glucosidase inhibitory activity. Most of derivatives, such as 9a–9e, 9i, 9m–9n and 11d–1e, (IC50 = 0.57 ± 0.01 μM to 8.45 ± 0.57 μM), exhibited higher inhibitory activity than the parent natural products and were by far more potent than the antidiabetic drug acarbose (IC50 = 57.01 ± 0.03 μM). Among these, 9e and 11d showed the most potent activity in a non-competitive manner. The binding processes between the two most potent compounds and α-glucosidase were spontaneous. Hydrophobic interactions were the main forces for the formation and stabilization of the enzyme - acetylphenol scaffold inhibitor complex, and induced the topography image changes and aggregation of α-glucosidase. In addition, everted intestinal sleeves in vitro and the maltose loading test in vivo further demonstrated the α-glucosidase inhibition of the two compounds, and our findings proved that they have significant postprandial hypoglycemic effects.

Total Synthesis of (-)-Peniphenone A

The asymmetric total synthesis of the polyketide benzannulated spiroketal natural product, (-)-peniphenone A, is reported. The key reaction in the synthesis involved sp3-sp2 Negishi cross-coupling between a chiral organozinc species and an aryl bromide to construct the challenging α-chiral β-aryl carbonyl motif present in the natural product. Access to the spiroketal possessing the correct stereochemistry was facilitated by an unusual thermodynamic resolution at C10. The synthesis was achieved in 14 steps (longest linear sequence) from commercially available 2,4-dihydroxybenzaldehyde in 6% overall yield. Investigations into a parallel approach required extension of Krische's enantioselective hydrogen-mediated C-C coupling to α-substituted alcohols and oxetane ring-opening with an aryllithium for assembly of the polyketide domain. These studies provide a useful foundation for further work toward the natural product family, members of which demonstrate significant activity against M. tuberculosis and offer continuing inspiration for the development of efficient new chemical methods.

Development of noviomimetics that modulate molecular chaperones and manifest neuroprotective effects

Heat shock protein 90 (Hsp90) is a chaperone under investigation for the treatment of cancer and neurodegenerative diseases. Neuroprotective Hsp90 C-terminal inhibitors derived from novobiocin (novologues) include KU-32 and KU-596. These novologues modulate molecular chaperones and result in an induction of Heat Shock Protein 70 (Hsp70). “Noviomimetics” replace the synthetically complex noviose sugar with a simple cyclohexyl moiety to maintain biological efficacy as compared to novologues KU-596 and KU-32. In this study, we further explore the development of noviomimetics and evaluate their efficacy using a luciferase refolding assay, immunoblot analysis, a c-jun assay, and an assay measuring mitochondrial bioenergetics. These new noviomimetics were designed and synthesized and found to induce Hsp70 and improve biological activity. Noviomimetics 39e and 40a were found to induce Hsp70 and exhibit promising effects in cellular assays.

Modified biphenyl Hsp90 C-terminal inhibitors for the treatment of cancer

Heat Shock Protein 90 (Hsp90) is a molecular chaperone under clinical investigation for the treatment of neurodegenerative diseases and cancer. Neuroprotective Hsp90 C-terminal inhibitors (novologues) contain a biaryl ring system, and include KU-596, which was modified and investigated for potential anti-cancer activity. Incorporation of a benzamide group onto the biaryl novologues in lieu of the acetamide yielded compounds that manifest anti-cancer activity. Further exploration of the central phenyl ring led to compounds with enhanced anti-proliferative activity. The design, synthesis, and evaluation of these new analogs against breast and prostate cancer cell lines is reported herein, where it was found that 8b and 10 manifest potent anti-proliferative activity and a robust degradation of Hsp90 client-dependent proteins.