609-25-6

Basic information

• Product Name: 5-METHYLPYROGALLOL
• Synonyms: 3,4,5-TRIHYDROXYTOLUENE;5-METHYLPYROGALLOL;Methylpyrogallol;5-Methyl-1,2,3-benzenetriol;5-Methylbenzene-1,2,3-triol
• CAS NO: 609-25-6
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.14
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 609-25-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 216.62°C (rough estimate)
• Flash Point: 166.5 °C
• Appearance: /
• Density: 1.2127 (rough estimate)
• Vapor Pressure: 0.000146mmHg at 25°C
• Refractive Index: 1.4638 (estimate)
• PKA: 9.40±0.15(Predicted)
• CAS DataBase Reference: 5-METHYLPYROGALLOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLPYROGALLOL(609-25-6)
• EPA Substance Registry System: 5-METHYLPYROGALLOL(609-25-6)

Safety Data

• Hazardous Substances Data: 609-25-6(Hazardous Substances Data)

Usage

Uses

5-Methylpyrogallol has been used in studies such as glyoxalase 1-?inhibition activity, and the mechanism of the xanthine oxidase (XO) inhibitory activity of pyrogallol as it is a compound closely related in structure to pyrogallol.

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

Upstream product

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• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 537-08-6 diploschistesic acid 
• 7722-84-1 dihydrogen peroxide 
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• 10034-85-2 hydrogen iodide 
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Downstream Products

• 65841-01-2 3,4-diacetoxy-5-methoxy-toluene 
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• 152898-04-9 14-benzyloxy-16-methylbenzo-1,4,7,10,13-pentaoxacyclopentadecane 
• 152898-02-7 4-benzyloxy-2-ethoxy-6-methyl-1,3-benzodioxole 
• 152898-30-1 3-benzyloxy-4,5-dimethoxytoluene 
• 152898-03-8 3-benzyloxy-5-methyl-1,2-benzenediol 
• 152898-31-2 3-allyloxy-4,5-dimethoxytoluene 
• 152898-19-6 3-allyloxy-5-methyl-1,2-benzenediol 
• 1128-32-1 2,3-dimethoxy-5-methylphenol 
• 606-06-4 2-[(E)-3,7-dimethyl-2,6-octadienyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone 
• 605-94-7 2,3-Dimethoxy-5-methyl-1,4-benzoquinone 
• 940289-77-0 2-methoxycarbonyl-6-methyl-4-(2,2,6-trimethyl-1,3-benzodioxol-4-yloxy)benzoic acid 

Relevant articles and documents

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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%.

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.