7382-59-4

Usage

Uses

Used in the Plastics Industry:
Guaiacylglycerol-beta-guaiacyl ether is used as a component in the development of biodegradable plastics for its ability to contribute to the creation of environmentally friendly materials that can reduce plastic pollution.
Used in the Adhesives Industry:
GGE is utilized as a key ingredient in the formulation of adhesives, leveraging its natural bonding properties to enhance the performance of these products while promoting sustainability.
Used in the Cosmetics and Skincare Industry:
Guaiacylglycerol-beta-guaiacyl ether is used as an antioxidant in anti-aging and skincare products, capitalizing on its ability to protect the skin from oxidative stress and potentially slow down the aging process.
Used in the Research and Development Sector:
GGE is employed as a subject of study for its potential applications across various industries, with ongoing research aimed at uncovering new uses and improving existing ones, thus contributing to a broader understanding of its capabilities and benefits.

InChI:InChI=1/C17H20O6/c1-21-13-5-3-4-6-14(13)23-16(10-18)17(20)11-7-8-12(19)15(9-11)22-2/h3-9,16-20H,10H2,1-2H3

Upstream product

• 22317-34-6 β-hydroxy-α-(2-methoxyphenoxy)4-hydroxy-3-methoxypropiophenone 
• 20730-75-0 1-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one 
• 1835-11-6 4-benzyloxy-3-methoxyacetophenone 
• 1835-12-7 3-methoxy-4-benzyloxy-α-bromoacetophenone 
• 22317-29-9 1-(4-(benzyloxy)-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one 
• 1252675-90-3 1-(4-benzoyloxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanone 
• 102834-26-4 4-benzoyloxy-3-methoxy-bromoacetylbenzene 
• 90-05-1 2-methoxy-phenol 
• 13078-21-2 ethyl 2-(2-methoxyphenoxy)acetate 
• 1878-85-9 (2-methoxyphenoxy)acetic acid 
• 91471-08-8 3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 36382-86-2 4-[3-Hydroxy-2-(2-methoxy-phenoxy)-prop-(Z)-ylidene]-2-methoxy-cyclohexa-2,5-dienone 
• 121-33-5 vanillin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 

Downstream Products

• 22347-86-0 trans-4-Hydroxy-3-methoxy-styrol-ω-sulfonsaeure 
• 14604-33-2 2-(2-Methoxy-phenoxy)-1-(3-methoxy-4-hydroxy-phenyl)-3-hydroxy-propan-1-sulfonsaeure 
• 19826-89-2 α-methanesulfonyloxy-p-bromoacetophenone 
• 19826-67-6 trans-4-Hydroxy-3-methoxy-styrol-ω-sulfonsaeure-methylester 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 458-35-5 coniferal alcohol 
• 102867-12-9 4-[1-Bromo-3-hydroxy-2-(2-methoxy-phenoxy)-propyl]-2-methoxy-phenol 
• 95316-34-0 3-Hydroxy-1-methoxy-2-(2-methoxy-phenoxy)-1-(4-hydroxy-3-methoxy-phenyl)-propan 
• 97357-06-7 2-<2-Methoxy-phenoxy>-1-<3-methoxy-4-benzyloxy-phenyl>-ethylen 
• 2196-18-1 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone 
• 90-05-1 2-methoxy-phenol 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 211366-64-2 Acetic acid 3-(4-acetoxy-3-methoxy-phenyl)-3-bromo-2-(2-methoxy-phenoxy)-propyl ester 
• 528814-97-3 dehydrodiconiferyl alcohol 

Relevant academic research and scientific papers

Are quinone methides responsible for yellowing of paper in light?

Irradiation of tetrahydrofuran solutions of quinone methide 1 at 350 nm resulted in the formation of yellow oligomeric products and guaiacol. The rate constants determined for the disappearance of the starting compound and those of guaiacol formation show

One-pot synthesis of β-O-4 lignin models: Via the insertion of stable 2-diazo-1,3-dicarbonyls into O-H bonds

Because lignin is a macromolecule that is a sustainable source of aromatic compounds, model substrates are commonly used to increase our understanding of its complex structure. However, few methods have been described for the synthesis of these models. Herein, we describe a new route towards the synthesis of β-O-4 lignin models by intermolecular O-H insertion reactions with simple and stable diazocarbonyls. The benefits of this developed method were shorter reaction times and high yields, as well as mild and environmentally friendly conditions. This journal is

Iridium-catalysed primary alcohol oxidation and hydrogen shuttling for the depolymerisation of lignin

Lignin is a potentially abundant renewable resource for the production of aromatic chemicals, however its selective depolymerisation is challenging. Here, we report a new catalytic system for the depolymerisation of lignin to novel, non-phenolic monoaromatic products based on the selective β-O-4 primary alcohol dehydrogenation with a Cp?Ir-bipyridonate catalyst complex under basic conditions. We show that this system is capable of promoting the depolymerisation of model compounds and isolated lignins via a sequence of selective primary alcohol dehydrogenation, retro-aldol (Cα-Cβ) bond cleavage and in situ stabilisation of the aldehyde products by transfer (de)hydrogenation to alcohols and carboxylic acids. This method was found to give good to excellent yields of cleavage products with both etherified and free-phenolic lignin model compounds and could be applied to real lignin to generate a range of novel non-phenolic monomers including diols and di-acids. We additionally show, by using the same catalyst in a convergent, one-pot procedure, that these products can be selectively channelled towards a single di-acid product, giving much simpler product mixtures as a result.

Transition-metal-free conversion of lignin model compounds to high-value aromatics: Scope and chemoselectivity

An efficient and straightforward reaction protocol for the conversion of lignin model compounds was developed based on a simple system consisting of a base, oxygen, and a green solvent under mild conditions in the absence of metals. This protocol was successfully applied to the cleavage of both 'β-O-4' dimeric and trimeric compounds, and a controlled selective degradation was achieved depending on the bond type. The feasibility of this method to provide aromatic compounds in high yields from lignin by a sequential oxidative dehomologation reaction was clearly demonstrated.

Method for synthesizing guaiacyl glycerol-beta-guaiacyl ether from lignin beta-O-4 linkage dimer model compound

The invention provides a method for synthesizing guaiacyl glycerol-beta-guaiacyl ether from a lignin beta-O-4 linkage dimer model compound. The content of beta-O-4 linkages in all linkages of lignin is highest and about 40-60%, so research of the beta-O-4 linkage lignin model compound plays an important role in research of the structure of lignin and the reaction mechanism of lignin in reaction. The method is simple, reaction conditions are mild, the yield is high, and the production period is short.

SELECTIVE AEROBIC ALCOHOL OXIDATION METHOD FOR CONVERSION OF LIGNIN INTO SIMPLE AROMATIC COMPOUNDS

Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Br?nsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.

Chemoselective metal-free aerobic alcohol oxidation in lignin

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts

We report a strategy for the catalytic conversion of lignosulfonate into phenols over heterogeneous nickel catalysts. Aryl-alkyl bonds (C-O-C) and hydroxyl groups (-OH) are hydrogenated to phenols and alkanes, respectively, without disturbing the arenes. The catalyst is based on a naturally abundant element, and is recyclable and reusable. The Royal Society of Chemistry 2012.

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.

Co(salen)/SBA-15 catalysed oxidation of a β-O-4 phenolic dimer under microwave irradiation

The microwave-assisted oxidative degradation of a lignin model phenolic dimer [1-(4-hydroxy-3-methoxyphenoxy)-2-(2-methoxyphenoxy)-propane-1,3-diol, 1] catalysed by Co(salen)/SBA-15 is reported. The investigated model compound 1 was prepared through a multistep synthesis and characterized by 1H, 13C NMR, and GC-MS studies. The catalyst was prepared by immobilizing [N,N′-bis(salicylidene)ethane-1,2-diaminato]Cobalt(II), Co(salen) complex onto the periodic mesopore channels of siliceous SBA-15. The activity of the Co(salen)/SBA-15 was investigated in the oxidation of 1 in the presence of hydrogen peroxide as oxidant, both under microwave irradiation and conventional heating. The phenolic dimer was selectively oxidized to 2-methoxy phenol with very high TON under microwave activation conditions. Comparatively, reactions run under conventional heating led to oligomerisation of the dimer and resulted in a mixture of products.