1124-39-6

Usage

Uses

4-Ethylcatechol is one of the main phenolic off-flavour markers in French ciders.

InChI:InChI=1/C8H10O2/c1-2-6-3-4-7(9)8(10)5-6/h3-5,9-10H,2H2,1H3

Upstream product

• 1197-09-7 1-(3,4-dihydroxyphenyl)ethan-1-one 
• 2785-89-9 4-Ethylguaiacol 
• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 31646-64-7 3,4-dihydroxy-1-vinylcyclohexane 
• 7732-18-5 water 
• 90-05-1 2-methoxy-phenol 
• 5888-51-7 4-ethylveratrole 
• 123-07-9 4-Ethylphenol 
• 123-31-9 hydroquinone 
• 64-17-5 ethanol 
• 120-80-9 benzene-1,2-diol 
• 5441-51-0 4-ethylcyclohexanone 
• 331-39-5 caffeic acid 
• 2785-88-8 5-ethyl-2-methoxyphenol 

Downstream Products

• 115328-27-3 4-ethyl-1,2-diacetoxybenzene 
• 1450663-84-9 C₂₁H₁₇NO₁₁ 
• 1429310-25-7 4'-(3-tert-butyl-5-hydroxy-1H-pyrazol-4-yl)-5'-ethylbenzene-1',2'-diol 
• 1521221-79-3 4-(benzo[d]oxazol-2'-ylthio)-5-ethylbenzene-1,2-diol 
• 1521221-81-7 4-(benzo[d]thiazol-2'-ylthio)-5-ethylbenzene-1,2-diol 
• 1521221-87-3 4-(4',5'-dihydrothiazol-2'-ylthio)-5-ethylbenzene-1,2-diol 
• 86505-42-2 3-ethylcyclopentanone 
• 101053-02-5 3-ethylcyclopentanol 
• 5888-51-7 4-ethylveratrole 
• 2785-89-9 4-Ethylguaiacol 
• 2785-88-8 5-ethyl-2-methoxyphenol 

Relevant academic research and scientific papers

Thermal decomposition of caffeic acid in model systems: Identification of novel tetraoxygenated phenylindan isomers and their stability in aqueous solution

Caffeic acid subjected to mild pyrolysis (225-226 °C) under vacuum resulted in rapid decarboxylation and the formation of simple catechol monomers as well as more complex cyclocondensed dimers and polymers. This reaction yielded the same spectrum of products as did acid-catalyzed cyclization of caffeic acid. The major pyrolysis products were identified by reversed-phase HPLC and LC-tandem mass spectrometry. Two novel compounds, identified by MS, 1H NMR, and 13C NMR as 1,3-cis- and 1,3-trans-tetraoxygenated phenylindans, were present as major products in both the caffeic acid pyrolysate and the acid-treated sample. The stability and reactivity of the pyrolysis products in weakly buffered aqueous solutions were determined concomitantly by measuring hydrogen peroxide generation and by monitoring the concentration of the individual components by reversed-phase HPLC. Such model studies may provide information pertaining to reaction mechanisms and the nature of the compounds involved in hydrogen peroxide formation in coffee.

Transetherification of guaiacol to o-ethoxyphenol with gamma Al 2O3 as a catalyst in supercritical ethanol

The production of chemicals from lignin and lignin depolymerisation products is a promising alternative route to replace fossil fuels. Transetherification of guaiacol, a lignin derived model compound, to o-ethoxyphenol with γ-Al2O3 as the catalyst in supercritical ethanol has been investigated. The best reaction condition is 280°C for 3 h, giving a yield of 42% with a selectivity of 86%. A reaction pathway is also proposed. Besides, this work provides an example for producing a longer chain ether from a short chain ether.

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.

Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu?SILP catalyst

The selective hydrodeoxygenation of hydroxyacetophenone derivatives is achieved opening a versatile pathway for the production of valuable substituted ethylphenols from readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75?SILP) show high activity and stability for a broad range of substrates without acidic co-catalysts. This journal is

Effects of Temperature on the Composition and Xanthine Oxidase Inhibitory Activities of Caffeic Acid Roasting Products

The high-temperature treatment of caffeic acid by a model reaction for the processing of foods by roasting enhanced its xanthine oxidase (XO) inhibitory activity. The thermal reaction products included various oligomeric compounds, whose structures were determined as being produced via the intermediate 4-vinylcatechol. Measurements of their XO inhibitory activities were also carried out. Among the identified oligomers, the coupling products of caffeic acid and vinylcatechol, which were mainly produced at 140-170 °C, presented stronger XO inhibitory activities than the other types of oligomers produced. Further reacted compounds, which were mainly formed at 200 °C by the addition or elimination of catechol unit in the oligomers, displayed weaker activities. These results indicated that thermal enhancement of the XO inhibitory activity of caffeic acid can be explained by the differences in the XO inhibitory activities of the various constituents of the thermal reaction products. Caffeic acid and its derivatives are polyphenols found widely distributed in foods. Moreover, XO inhibition is closely related to the prevention of the life-style-related disease gout. The results suggest that a simple roasting process (170 °C) can lend useful human-health-related functionalities to caffeic acid containing foods such as coffee.

Conversion of Simple Cyclohexanones into Catechols

A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.

Chemo- and Regioselective Hydrogenolysis of Diaryl Ether C-O Bonds by a Robust Heterogeneous Ni/C Catalyst: Applications to the Cleavage of Complex Lignin-Related Fragments

We report the chemo- and regioselective hydrogenolysis of the C-O bonds in di-ortho-substituted diaryl ethers under the catalysis of a supported nickel catalyst. The catalyst comprises heterogeneous nickel particles supported on activated carbon and furnishes arenes and phenols in high yields without hydrogenation. The high thermal stability of the embedded metal particles allows C-O bond cleavage to occur in highly substituted diaryl ether units akin to those in lignin. Preliminary mechanistic experiments show that this catalyst undergoes sintering less readily than previously reported catalyst particles that form from a solution of [Ni(cod)2].