890317-92-7

Usage

Uses

Used in Biochemistry Research:
Erythro-Guaiacylglycerol beta-coniferyl ether is used as a subject of study in biochemistry research for its role in the plant cell wall structure, which helps in understanding the mechanisms of plant growth and development.
Used in Materials Science:
Erythro-Guaiacylglycerol beta-coniferyl ether is used as a component in materials science for its potential applications in the development of sustainable materials, such as bio-based polymers and composites, that can replace petroleum-based materials.
Used in Biofuels Development:
Erythro-Guaiacylglycerol beta-coniferyl ether is used as a precursor in the development of biofuels, as lignin-derived compounds can be converted into valuable chemicals and energy sources, contributing to a sustainable energy future.
Used in Plant Cell Wall Modification:
Erythro-Guaiacylglycerol beta-coniferyl ether is used as a target for plant cell wall modification, aiming to improve plant properties such as mechanical strength, flexibility, and resistance to environmental stress, which can enhance crop performance and resilience.

Upstream product

• 458-35-5 coniferal alcohol 
• 458-35-5 coniferol 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 92409-34-2 1-(4-hydroxy-3,5-dimethoxyphenyl)-2-(2'-methoxyphenoxy)-1,3-propanediol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 2480-86-6 Apocynol 
• 1350889-91-6 (7S,8R)-9'-[β-D-apiofuranosyl-(1->6)-β-D-glucopyranosyloxy]-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-4,7,9-triol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 904914-50-7 Benzoic acid 4-{3-hydroxy-2-[2-methoxy-4-((E)-3-oxo-propenyl)-phenoxy]-propionyl}-2-methoxy-phenyl ester 
• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 
• 121-33-5 vanillin 

Relevant academic research and scientific papers

Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling

We have studied the regioselectivity of oxidative phenol coupling in lignin formation using an oxidation system that distinguishes between dimerization reactions and cross-coupling reactions. We found that the regioselectivity of coupling was different in the two reactions. For instance, in coniferyl alcohol dimerization the formation of β-5 coupling product has a slight prevalence over the formation of β-O-4 product; in cross-coupling the β-0-4 mode is favoured in a ratio of ≈10:1. This ratio is higher than that found in isolated softwood lignins. The degree of cross-coupling was influenced only to a small extent by changes in the rates of conventional addition of coniferyl alcohol (Zulauf versus Zutropf conditions). We found that diffusion through a dialysis membrane did effectively suppress the dimerization of coniferyl alcohol. Of the different oxidants investigated, manganese triacetate in acetic acid yielded the highest proportion of cross-coupling product. The Royal Society of Chemistry 2000.

Structures of new aromatics glycosides from a Japanese folk medicine, the roots of Angelica furcijuga

Three new aromatics glycosides, hyuganosides II, IIIa, and IIIb, were isolated from a Japanese folk medicine, the roots of Angelica furcijuga KITAGAWA. The structures of the new glycosides were determined on the basis of chemical and physicochemical evide

In vitro activity-guided identification of antioxidants in aged garlic extract

Activity-guided fractionation was applied on an aged garlic extract (AGE), reported to show strong antioxidant activity, in order to locate the key in vitro antioxidant ingredients by means of the hydrogen peroxide scavenging (HPS) assay as well as the OR

Incorporation of catechyl monomers into lignins: Lignification from the non-phenolic end: Via Diels-Alder cycloaddition?

Canonical lignification occurs via the coupling of phenolic radicals, in which chain extension can occur only from phenolic ends of growing polymer chains. Radical coupling of catechyl monomers, including caffeyl and 5-hydroxyconiferyl alcohols, gives ris

Biomimetic Oxidation of Monolignol Acetate and p-Coumarate by Silver Oxide in 1,4-Dioxane

Lignin acylated with acetate and/or p-coumarate is common in many herbaceous plants. Herein, the biomimetic oxidation of ?3-acylated monolignols with Ag2O was studied to understand the effect of ?3-acyl groups on monolignol polymerization. The oxidation of sinapyl acetate gave ?3-acylated and α-acylated β-O-4 dimers in 71 and 9.5% yields, respectively. The oxidation of sinapyl p-coumarate produced ?3-acylated β-O-4 and ?3-acylated tetralin β-β dimers in 53 and 16% yields, respectively. Only the sinapyl alcohol moiety in sinapyl p-coumarate reacted, and the p-coumarate moiety remained unchanged, suggesting that p-coumaric acid is not incorporated into the lignin backbone in the acylated lignins. All of the ?3-acylated monolignols used in this study produced the ?3-acylated β-O-4 dimers, which suggests that the ?3-acylated monolignols act as lignin monomers. The relatively high yields of the β-O-4 dimers indicate that Ag2O oxidation of the monolignols can be used as an easy method for synthesizing the β-O-4 dimer model compounds.

Three new lignan glycosides from the Firmiana simplex

In our quest for structurally intriguing compounds from Korean medicinal plant sources, chromatographic separation of the 80% MeOH extract from Firmiana simplex resulted in the isolation and identification of three new lignan glycosides (1-3), together with six known lignan glycosides (4-9). The structures of 1-3 were determined on the basis of spectroscopic analyses, including extensive 2D-NMR and enzyme hydrolysis. Nitric oxide (NO) production was evaluated in the lipopolysaccharide-Activated microglial cell line, BV-2 to investigate the anti-neuroinflammatory effects of the isolated compounds (1-9). Compound 7 marginally inhibited NO levels with IC50 values of 59.83 μM.

Anti selective glycolate aldol reactions of (: S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one: application towards the asymmetric synthesis of 8-4′-oxyneolignans

The anti selective glycolate aldol reactions of (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one auxiliary have been standardized with high yields and excellent diastereoselectivities on various substituted aryl, allyl and alkyl aldehydes. The optimized reaction conditions were employed for the stereoselective synthesis of oxyneolignans.

The synthesis and analysis of advanced lignin model polymers

If the lignin-first biorefinery concept becomes a reality, high quality lignins close in structure to native lignins will become available in large quantities. One potential way to utilise this renewable material is through depolymerisation to aromatic chemicals. This will require the development of new chemical methods. Here, we report the synthesis and characterisation of advanced lignin model polymers to be used as tools to develop these methods. The controlled incorporation of the major linkages in lignin is demonstrated to give complex hardwood and softwood lignin model polymers. These polymers have been characterised by 2D HSQC NMR and GPC analysis and have been compared to isolated lignins.

On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride

Some ionic liquids are able to dissolve wood, including lignin and lignocellulose, and thus they provide an efficient reaction media for modification of globally abundant wood-based polymers. Lignin can be modified with laccases (EC 1.10.3.2), multicopper

Synthesis and characterization of new 5-linked pinoresinol lignin models

Pinoresinol structures, featuring a β-β′-linkage between lignin monomer units, are important in softwood lignins and in dicots and monocots, particularly those that are downregulated in syringyl-specific genes. Although readily detected by NMR spectroscopy, pinoresinol structures largely escaped detection by β-ether-cleaving degradation analyses presumably due to the presence of the linkages at the 5 positions, in 5-5′- or 5-O-4′-structures. In this study, which is aimed at helping better understand 5-linked pinoresinol structures by providing the required data for NMR characterization, new lignin model compounds were synthesized through biomimetic peroxidase-mediated oxidative coupling reactions between pre-formed (free-phenolic) coniferyl alcohol 5-5′- or 5-O-4′-linked dimers and a coniferyl alcohol monomer. It was found that such dimers containing free-phenolic coniferyl alcohol moieties can cross-couple with the coniferyl alcohol producing pinoresinol-containing trimers (and higher oligomers) in addition to other homo- and cross-coupled products. Eight new lignin model compounds were obtained and characterized by NMR spectroscopy, and one tentatively identified cross-coupled β-O-4′-product was formed from a coniferyl alcohol 5-O-4′-linked dimer. It was demonstrated that the 5-5′- and 5-O-4′-linked pinoresinol structures could be readily differentiated by using heteronuclear multiple-bond correlation (HMBC) NMR spectroscopy. With appropriate modification (etherification or acetylation) to the newly obtained model compounds, it would be possible to identify the 5-5′- or 5-O-4′-linked pinoresinol structures in softwood lignins by 2D HMBCN MR spectroscopic methods. Identification of the cross-coupled dibenzodioxocin from a coniferyl alcohol 5-5′-linked moiety suggested that thioacidolysis or derivatization followed by reductive cleavage (DFRC) could be used to detect and identify whether the coniferyl alcohol itself undergoes 5-5′-cross-linking during lignification. Super model: In this study, aimed at helping to better understand 5-linked pinoresinol structures by providing the required data for NMR structural characterization, new lignin model pinoresinol compounds were synthesized through biomimetic peroxidase-mediated oxidative coupling between pre-formed (free-phenolic) 5-5′- or 5-O-4′-linked coniferyl alcohol dimers and a coniferyl alcohol monomer (examples with 5-O-4′-linked dimers are shown in the scheme).