20491-92-3

Basic information

• Product Name: 2,4,6-Trimethoxyphenol
• Synonyms: 2-HYDROXY-1,3,5-TRIMETHOXYBENZENE;2,4,6-TRIMETHOXYPHENOL;2,4,6-Trimethoxyphen
• CAS NO: 20491-92-3
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19
• EINECS: 243-851-5
• Product Categories: Aromatic Phenols
• Mol File: 20491-92-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 60-64 °C
• Boiling Point: 308.108 °C at 760 mmHg
• Flash Point: 140.139 °C
• Appearance: /
• Density: 1.152 g/cm³
• Vapor Pressure: 0.000382mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.48±0.23(Predicted)
• CAS DataBase Reference: 2,4,6-Trimethoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trimethoxyphenol(20491-92-3)
• EPA Substance Registry System: 2,4,6-Trimethoxyphenol(20491-92-3)

Safety Data

• Hazardous Substances Data: 20491-92-3(Hazardous Substances Data)

Usage

Uses

2,4,6-Trimethoxyphenol is a natural product identified in the methanol extracts from the trunk bark of Ceiba pentandra. Shows antioxidant activity.

InChI:InChI=1/C9H12O4/c1-11-6-4-7(12-2)9(10)8(5-6)13-3/h4-5,10H,1-3H3

Upstream product

• 124-41-4 sodium methylate 
• 118-79-6 2,4,6-tribromophenol 
• 108-95-2 phenol 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 83013-65-4 1-(O-2,4,6-trimethoxyphenyl)-6-(O-galloyl)-β-D-glucopyranoside 
• 530-55-2 2,6-dimethoxy-p-quinone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 15233-65-5 2,6-dimethoxy-1,4-hydroquinone 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 60855-15-4 3-methoxy-[1,2]benzoquinone 
• 30225-90-2 2,4,6-trimethoxyphenyl acetate 
• 30225-92-4 2,4,6-Trimethoxy-formyloxybenzol 
• 125288-25-7 1-(O-2,4,6-trimethoxyphenyl)-β-D-glucopyranoside 

Downstream Products

• 7505-18-2 chloro-acetic acid-(2,4,6-trimethoxy-phenyl ester) 
• 112221-42-8 2-(3,4-Dimethoxy-phenoxy)-1,3,5-trimethoxy-benzene 
• 119892-40-9 6-hydroxy-5,7-dimethoxyflavone 
• 103777-45-3 5-hydroxy-2,4,6-trimethoxyacetophenone 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 184218-99-3 C₉H₁₃O₄ 
• 637-31-0 4,4'-bis(dimethylamino)diphenylamine 
• 1357013-04-7 2,4,6-trimethoxyphenyl (4-(trimethylsilyl)but-3-yn-2-yl) carbonate 
• 1357013-17-2 5-((tert-butyldimethylsilyl)oxy)-1-phenylpent-1-yn-3-yl (2,4,6-trimethoxyphenyl)carbonate 
• 1357013-16-1 4-phenylbut-3-yn-2-yl (2,4,6-trimethoxyphenyl) carbonate 
• 1357013-15-0 2,2-dimethylnon-3-yn-5-yl (2,4,6-trimethoxyphenyl) carbonate 
• 1357013-14-9 hex-4-yn-3-yl (2,4,6-trimethoxyphenyl) carbonate 
• 1357013-13-8 tert-butyl 3-(5-(((2,4,6-trimethoxyphenoxy)carbonyl)oxy)-7-(trimethylsilyl)hept-6-yn-1-yl)-1H-indole-1-carboxylate 
• 22804-60-0 2-Hydroxy-2',3,4,6,6'-pentamethoxy-benzophenon 

Relevant articles and documents

Inositol to aromatics –benzene free synthesis of poly oxygenated aromatics

A method for the preparation of benzene derivatives from myo-inositol, an abundantly available phyto chemical is described. 1,3-Bridged acetals of inososes undergo step-wise elimination leading to the formation of polyoxygenated benzene derivatives. This aromatization reaction proceeds through the intermediacy of a β-alkoxyenone, which could be isolated. This sequence of reactions starting from myo-inositol, provides a novel route for the preparation of polyoxygenated benzene derivatives including polyoxygenated biphenyl. This scheme of synthesis demonstrates the potential of myo-inositol as a sustainable non-petrochemical resource for aromatic compounds.

Investigation of the mechanism of action of pyrogallol-phloroglucinol transhydroxylase by using putative intermediates

Pyrogallol-phloroglucinol transhydroxylase from Pelobacter acidigallici, a molybdopterin-containing enzyme, catalyzes a key reaction in the anaerobic degradation of aromatic compounds. In vitro, the enzymatic reaction requires 1,2,3,5-tetrahydroxy-benzene as a cocatalyst and the trans-hydroxylation occurs without exchange with hydroxy groups from water. To test our previous proposal that the transfer of the hydroxy group occurs via 2,4,6,3′,4′, 5′-hexahydroxydiphenyl ether as an intermediate, we synthesized this compound and investigated its properties. We also describe the synthesis and characterization of 3,4,5,3′,4′,5′-hexahydroxydiphenyl ether. Both compounds could substitute for the cocatalyst in vitro. This indicates that the diphenyl ethers can intrude into the active site and initiate the catalytic cycle. Recently, the X-ray crystal structure of the transhydroxylase (TH) was published[16] and it supports the proposed mechanism of hydroxy-group transfer.

Method for the production of alkoxy- and aryloxy-phenols

Alkoxybenzaldehydes and aryloxybenzaldehydes are converted to the corresponding phenols by reacting the benzaldehydes in an organic solvent phase with formic acid and hydrogen peroxide in an aqueous solvent phase to produce the corresponding formate ester. The formate ester is then saponified to produce the corresponding phenol.