98751-47-4

Upstream product

• 77891-26-0 1-(4-ethoxy-3-methoxyphenyl)propane-1,2,3-triol 
• 186255-41-4 1-(4-ethoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanone 
• 77891-30-6 1-(4-ethoxy-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one 
• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 84159-64-8 4-ethoxy-3-methoxybromoacetylbenzene 
• 75665-89-3 1-<(4-ethoxy-3-methoxy)phenyl>ethan-1-one 
• 22317-29-9 1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 
• 22317-34-6 β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 

Relevant academic research and scientific papers

Role of laccase as an enzymatic pretreatment method to improve lignocellulosic saccharification

The recalcitrant nature of lignocellulose, in particular due to the presence of lignin, is found to decrease the efficiency of cellulases during the saccharification of biomass. The efficient and cost effective removal of lignin is currently a critical bi

Alkoxyl- and carbon-centered radicals as primary agents for degrading non-phenolic lignin-substructure model compounds

Lignin degradation by white-rot fungi proceeds via free radical reaction catalyzed by oxidative enzymes and metabolites. Basidiomycetes called selective white-rot fungi degrade both phenolic and non-phenolic lignin substructures without penetration of extracellular enzymes into the cell wall. Extracellular lipid peroxidation has been proposed as a possible ligninolytic mechanism, and radical species degrading the recalcitrant non-phenolic lignin substructures have been discussed. Reactions between the non-phenolic lignin model compounds and radicals produced from azo compounds in air have previously been analysed, and peroxyl radical (PR) is postulated to be responsible for lignin degradation (Kapich et al., FEBS Lett., 1999, 461, 115-119). However, because the thermolysis of azo compounds in air generates both a carbon-centred radical (CR) and a peroxyl radical (PR), we re-examined the reactivity of the three radicals alkoxyl radical (AR), CR and PR towards non-phenolic monomeric and dimeric lignin model compounds. The dimeric lignin model compound is degraded by CR produced by reaction of 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH), which under N2 atmosphere cleaves the α-β bond in 1-(4-ethoxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol to yield 4-ethoxy-3-methoxybenzaldehyde. However, it is not degraded by the PR produced by reaction of Ce4+/tert-BuOOH. In addition, it is degraded by AR produced by reaction of Ti3+/tert-BuOOH. PR and AR are generated in the presence and absence of veratryl alcohol, respectively. Rapid-flow ESR analysis of the radical species demonstrates that AR but not PR reacts with the lignin model compound. Thus, AR and CR are primary agents for the degradation of non-phenolic lignin substructures.

Singlet oxygen in the photodegradation of lignin models

The photochemical oxidation of lignin models in the presence of singlet oxygen was studied. The treatment of the non-phenolic β-O-4 aryl ether derivatives 6, 7, and 8 in the presence of both oxygen and Rose Bengal gave products deriving from a formal β-C-O cleavage formation. By this way. the derivatives 12, 13, and 15 were obtained. The photochemical oxidation of the phenolic β-O-4 aryl ether 9 gave the same type of product confirming that, in this case, the presence of the carbonyl group is not indispensable to have the cleavage reaction. The use of the model compound 10 showed that, when the phenoxy part of the molecule shows a lower reactivity towards singlet oxygen, the oxidation of the phenol moiety to hydroquinone call occur. The photochemical behaviour of these model compounds can be rationalised from a reaction of singlet oxygen with the phenoxy part of the molecule.

Metabolism of a Non-phenolic β-O-4 Lignin Substructure Model Compound by Coriolus versicolor

A non-phenolic β-O-4 lignin substructure model, 4-ethoxy-3-methoxyphenylglycerol-β-syringaldehyde ether (I), was metabolized by a ligninolytic culture of Coriolus versicolor.Based on the identification of the metbaolic products (II-X1), the following reactions were found to occur in the culture; a) oxidation (III) and reduction (II) at the benzyl (Cα') position of the substrate (I), b) β-ether cleavage to give arylglycerols (IV, V), and c) Cα-Cβ cleavage of the arylglycerols and/or arylglycerol moiety of the substrate (I).In addition, β-deoxy diol (VI) and γ-formylglycerol (VII) were obtained as degradation products from substrate (I).