609-25-6

Usage

Uses

Used in Pharmaceutical Research:
5-METHYLPYROGALLOL is used as a research compound for studying its inhibitory activity on enzymes such as glyoxalase 1. This enzyme plays a crucial role in cellular detoxification processes, and its inhibition can have potential therapeutic implications in treating certain diseases.
Used in Enzyme Inhibition Studies:
In the field of biochemistry, 5-METHYLPYROGALLOL is used as a compound to investigate the mechanism of xanthine oxidase (XO) inhibitory activity. Xanthine oxidase is an enzyme involved in purine metabolism, and its inhibition can be beneficial in managing conditions like gout and reducing oxidative stress.
Used in Chemical Synthesis:
5-METHYLPYROGALLOL can be used as a starting material or intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable building block in organic synthesis.
Used in Analytical Chemistry:
Due to its chemical properties, 5-METHYLPYROGALLOL can be employed as a reagent or reference compound in analytical chemistry. It can be used for the development of analytical methods, calibration of instruments, or as a standard in quality control processes.
Used in Material Science:
The unique structure and properties of 5-METHYLPYROGALLOL can also find applications in material science. It can be used in the development of new materials with specific properties, such as conductive polymers, sensors, or other advanced materials with potential applications in various industries.

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

Upstream product

• 6638-05-7 2,6-dimethoxy-4-methylphenol 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 91910-99-5 3,4,5-triacetoxy-toluene 
• 19104-07-5 methyl 3-hydroxy orsellinate 
• 7647-01-0 hydrogenchloride 
• 10034-85-2 hydrogen iodide 
• 526-37-4 atranol 
• 7722-84-1 dihydrogen peroxide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 79831-88-2 3,4,5-tribenzyloxybenzyl alcohol 
• 99-24-1 methyl galloate 
• 504-15-4 orcinol 
• 121287-34-1 2,6-bis(methoxymethyloxy)-4-methylbenzaldehyde 
• 82265-37-0 1,3-bis(methoxymethoxy)-5-methylbenzene 

Downstream Products

• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 91910-99-5 3,4,5-triacetoxy-toluene 
• 13997-12-1 2-methoxy-5-methyl-resorcinol 
• 1125-67-3 3-methoxy-5-methylbenzene-1,2-diol 
• 6443-69-2 3,4,5-trimethoxytoluene 
• 940289-74-7 dimethyl 3-methyl-5-(2,2,6-trimethyl-1,3-benzodioxol-4-yloxy)phthalate 
• 940289-75-8 2-methoxycarbonyl-3-methyl-5-(2,2,6-trimethyl-1,3-benzodioxol-4-yloxy)benzoic acid 
• 940289-76-9 3-methyl-5-(2,2,6-trimethyl-1,3-benzodioxol-4-yloxy)phthalic acid 
• 940289-77-0 2-methoxycarbonyl-6-methyl-4-(2,2,6-trimethyl-1,3-benzodioxol-4-yloxy)benzoic acid 
• 65841-01-2 3,4-diacetoxy-5-methoxy-toluene 
• 152898-20-9 17-benzyloxy-19-methylbenzo-1,4,7,10,13,16-hexaoxacyclooctadecane 

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.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities

Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values 25 μM

Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds

Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.

Unusual polycyclic fused product by oxidative enzymatic dimerisation of 5-methylpyrogallol catalysed by horseradish peroxidase/H2O2

During investigations on the peroxidase-catalysed oxidation of polyhydroxylated monoaromatic substrates such as 5-methylpyrogallol, we observed a spectacular dimerisation proceeding by dearomatisation in contrast with most common reaction patterns involvi

Synthesis method of substituted pyrogallols

The invention relates to a synthesis method of substituted pyrogallols, belonging to the field of organic synthesis. The method comprises the following steps: by using aryloxy pyridines as a raw material, carrying out reaction in an organic solvent at 60-

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Evaluation of the pharmacophoric motif of the caged Garcinia xanthones

The combination of unique structure and potent bioactivity exhibited by several family members of the caged Garcinia xanthones, led us to evaluate their pharmacophore. We have developed a Pd(0)-catalyzed method for the reverse prenylation of catechols tha

Synthesis of crown ethers related to ubiquinones

Crown ethers in which the two methoxy groups of ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) are replaced by oligoethylene glycol bridges have been obtained in five straightforward steps in 35-40% overall yield from 5-methylpyrogallol. A Fremy salt oxidation of a phenolic precursor is used in the final step. The further elaboration of crown ether analogues of ubiquinone-2 was achieved by enol geranylation of cyclopentadiene adducts of the former quinones and subsequent retro-Diels-Alder reaction. The Claisen rearrangement of 2,2-dimethoxy-5-methylphenyl allyl ethers and related crown ethers affords ortho- and para-allyl-substituted phenols (3:1) that are oxidized to give bisnorubiquinone derivatives and their ortho-quinone isomers. All new compounds are characterized by high resolution NMR and mass spectrometry.

Production of organic compounds

Pyrogallol, and analogues thereof having an alkyl, carboxy or alkoxycarbonyl substituent in the benzene ring, and their salts, are prepared by oxidizing, preferably by hydrogen peroxide, the corresponding compounds in which 1 or 2 of the OH groups are replaced by --COR5 groups where R5 represents hydrogen, alkyl or phenylalkyl. The production of intermediates is also described and some of these are novel.