824-46-4

Usage

Uses

Used in Biochemical Processes:
2-Methoxyhydroquinone is utilized in the conversion of ferulic acid to coniferyl alcohol by the white rot fungus Trametes. This process is significant in the field of biochemistry, as it demonstrates the ability of certain fungi to catalyze reactions that are otherwise challenging to achieve synthetically.
Used in Chemical Synthesis:
As a member of phenols, 2-methoxyhydroquinone can be employed as a starting material or intermediate in the synthesis of various organic compounds. Its reactivity and functional groups make it a versatile building block for the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Analytical Chemistry:
The unique chemical properties of 2-methoxyhydroquinone also make it useful in analytical chemistry for the detection and quantification of certain compounds. Its ability to form complexes or undergo specific reactions can be harnessed to develop analytical methods for monitoring environmental pollutants or tracking the presence of target molecules in various samples.

InChI:InChI=1/C7H8O3/c1-10-7-4-5(8)2-3-6(7)9/h2-4,8-9H,1H3

Upstream product

• 109194-60-7 tachioside 
• 31427-08-4 tachioside 
• 89232-58-6 O-(3-methoxyphenyl)hydroxylamine 
• 18278-34-7 4-hydroxy-2-methoxybenzaldehyde 
• 7722-84-1 dihydrogen peroxide 
• 121-33-5 vanillin 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 3904-22-1 2-methoxy-1,4-di-O-propanoylhydroquinone 
• 1193330-69-6 2-methoxy-4-hydroxyphenol 1-O-β-D-xylopyranosyl-(1->6)-β-D-glucopyranoside 
• 563-79-1 2,3-Dimethyl-2-butene 
• 150-19-6 O-methylresorcine 
• 90-05-1 2-methoxy-phenol 
• 100-66-3 methoxybenzene 
• 67431-17-8 4-hydroxy-3-methoxyphenyl formate 

Downstream Products

• 51281-73-3 2-(2',5'-dihydroxy-4'-methoxyphenyl)-5-methoxy-p-benzoquinone 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 43042-33-7 4,4'-Dimethoxybiphenyl-2,5,2',5'-bis-p-benzoquinone 
• 156570-79-5 2,3,5-tribromo-6-methoxy[1,4]benzoquinone 
• 75514-03-3 2-methoxy-p-hydroquinone diacetate 
• 99866-14-5 (2,5-dihydroxy-4-methoxy-phenyl)-glyoxylic acid ethyl ester 
• 58035-80-6 2-(2,5-Dihydroxy-4-methoxy-benzylamino)-4-methylsulfanyl-butyric acid 
• 136558-64-0 1-(3,4-Dihydro-6-hydroxy-7-methoxy-4-phenyl-2H-1-benzopyran-2-yl)morpholine 
• 70128-22-2 2-methoxy-1,4-benzoquinone anion radical 
• 36376-14-4 2,5-dimethoxy-1,4-benzoquinone anion radical 
• 74700-84-8 5-methoxy-2-(1-phenylethyl)benzene-1,4-diol 
• 84219-45-4 C₂₃H₂₀O₇ 
• 78018-54-9 1,4-bis(tert-butyldimethylsilyloxy)-2-methoxybenzene 
• 148460-98-4 1,4-Bis(1-ethoxyethoxy)-2-methoxybenzene 

Relevant academic research and scientific papers

Control of reaction pathways in the photochemical reaction of a quinone with tetramethylethylene by metal binding

The present study reports a novel supramolecular photochemical reaction that focuses on the direct electronic interactions between a host reaction substrate and guest metal salts. The reaction pathways in the photochemical reactions of quinone derivatives bearing a methoxy group and a long oligoether sidearm QEn (n = 0 and 3) with tetramethylethylene (TME) are changed upon noncovalent complexations of the host reactant with alkali and alkaline earth metal ions and a transition metal salt. The photochemical reaction of QEn with TME provides a mixture of [2 + 2] cycloadducts 1aE n and 1bEn, hydroquinone H2QEn, and monoallyl ether adducts of hydroquinones 2aEn and 2bEn. The photochemical reaction proceeds by the photoinduced electron transfer mechanism, where photoirradiation brings about formation of a radical ion pair [QEn-, TME+] as the primary intermediate. We found that the yields and selectivity of these photoproducts are changed upon electronic interactions of QEn- with the metal salts. The photochemical reaction in the absence of metal salts provides H 2QEn as its major product, whereas QE3, having the long sidearm, dominantly produces 2aE3 at the expense of 1aE 3, 1bE3, and H2QE3 when it forms a size-favorable host-guest complex with divalent Ca2+. In contrast, QEn selectively provides oxetanes 1aEn and 1bEn in the presence of Pd(OAc)2, which can form complexes with the quinone through metal-olefin and coordination interactions in the ground and photoexcited states of the quinone. This journal is the Partner Organisations 2014.

2-Methoxyhydroquinone from Vanillin for Aqueous Redox-Flow Batteries

We show the synthesis of a redox-active quinone, 2-methoxy-1,4-hydroquinone (MHQ), from a bio-based feedstock and its suitability as electrolyte in aqueous redox flow batteries. We identified semiquinone intermediates at insufficiently low pH and quinoid radicals as responsible for decomposition of MHQ under electrochemical conditions. Both can be avoided and/or stabilized, respectively, using H3PO4 electrolyte, allowing for reversible cycling in a redox flow battery for hundreds of cycles.

AROMATIC GLYCOSIDES FROM BERCHEMIA RACEMOSA

Key Word Index-Berchemia racemosa; Rhamnaceae; lignan; aromatic glycoside; nudiposide; secoisolariciresinol glucoside; isotachioside; tachioside; syringic acid glucosyl ester; 13C NMR. Two new aromatic glucosides have been isolated from the stems of Berchemia racemosa together with the known glycosides, nudiposide, (-)-secoisolariciresinol-O-β-D-glucopyranoside and methoxyhydroquinone-1-O-β-D-glucopyranoside (isotachioside).The structures of the new glucosides were found to be β-D-glucopyranosyl syringate, and methoxyhydroquinone-4-O-β-D-glucopyranoside on the basis of chemical and spectral evidences.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications

The synthetic feasibility of the oxidative cleavage: epoxidation of 7-O-geranylscopoletin followed by electrocyclic ring-opening, proposed in the biogenesis of transtaganolides/basiliolides is studied. Unlike the proposed pericyclic reactions, this pathway has not yet been addressed. Three synthetic strategies have been tested consisting of: i) Baeyer–Villiger oxidation of p-quinoids, ii) hydrolysis of quinone monoketals, or iii) direct fragmentation by using oxygen donors. Oxidation of the benzene ring of hydroxylated coumarins has been achieved using peroxyacids, but cleavage took place between undesired positions. The aromaticity conservation of the pyran-2-one cycle during oxidation is the controlling factor of these observed regioselectivities. The use of a 4,5-dihydroxy-2-methoxycinnamate model, in which the pyran-2-one ring does not exert influence on oxidation, has allowed the design of a synthetic sequence toward an analogue of the natural pyran-2-one isolated from Thapsia transtagana, key in the biogenesis. Mechanistic proposals for the obtained results as well as their biogenetic implications are raised.

FLAME-RETARDANT VANILLIN-DERIVED SMALL MOLECULES

A flame-retardant vanillin-derived small molecule, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived small molecule are disclosed. The flame-retardant vanillin-derived small molecule can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, or thioether substituents. The process for forming the flame-retardant polymer can include reacting a diol vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived small molecule, and binding the flame-retardant vanillin-derived small molecule to a polymer. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived small molecules. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

FLAME-RETARDANT VANILLIN-DERIVED MONOMERS

A flame-retardant vanillin-derived monomer, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains flame-retardant vanillin-derived monomer are disclosed. The flame-retardant vanillin-derived monomer can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, epoxide, or propylene carbonate substituents. The process for forming the flame-retardant polymer can include reacting a vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived monomer, and then polymerizing the flame-retardant vanillin-derived monomer. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived monomer. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

Sphingobacterium sp. T2 Manganese Superoxide Dismutase Catalyzes the Oxidative Demethylation of Polymeric Lignin via Generation of Hydroxyl Radical

Sphingobacterium sp. T2 contains two extracellular manganese superoxide dismutase enzymes which exhibit unprecedented activity for lignin oxidation but via an unknown mechanism. Enzymatic treatment of lignin model compounds gave products whose structures were indicative of aryl-Cα oxidative cleavage and demethylation, as well as alkene dihydroxylation and alcohol oxidation. 18O labeling studies on the SpMnSOD-catalyzed oxidation of lignin model compound guiaiacylglycerol-β-guaiacyl ether indicated that the an oxygen atom inserted by the enzyme is derived from superoxide or peroxide. Analysis of an alkali lignin treated by SpMnSOD1 by quantitative 31P NMR spectroscopy demonstrated 20-40% increases in phenolic and aliphatic OH content, consistent with lignin demethylation and some internal oxidative cleavage reactions. Assay for hydroxyl radical generation using a fluorometric hydroxyphenylfluorescein assay revealed the release of 4.1 molar equivalents of hydroxyl radical by SpMnSOD1. Four amino acid replacements in SpMnSOD1 were investigated, and A31H or Y27H site-directed mutant enzymes were found to show no lignin demethylation activity according to 31P NMR analysis. Structure determination of the A31H and Y27H mutant enzymes reveals the repositioning of an N-terminal protein loop, leading to widening of a solvent channel at the dimer interface, which would provide increased solvent access to the Mn center for hydroxyl radical generation.

Enzyme-Catalysed Synthesis of Cyclohex-2-en-1-one cis-Diols from Substituted Phenols, Anilines and Derived 4-Hydroxycyclohex-2-en-1-ones

Toluene dioxygenase-catalysed cis-dihydroxylations of substituted aniline and phenol substrates, with a Pseudomonas putida UV4 mutant strain and an Escherichia coli pCL-4t recombinant strain, yielded identical arene cis-dihydrodiols, which were isolated as the preferred cyclohex-2-en-1-one cis-diol tautomers. These cis-diol metabolites were predicted by preliminary molecular docking studies, of anilines and phenols, at the active site of toluene dioxygenase. Further biotransformations of cyclohex-2-en-1-one cis-diol and hydroquinone metabolites, using Pseudomonas putida UV4 whole cells, were found to yield 4-hydroxycyclohex-2-en-1-ones as a new type of phenol bioproduct. Multistep pathways, involving ene reductase- and carbonyl reductase-catalysed reactions, were proposed to account for the production of 4-hydroxycyclohex-2-en-1-one metabolites. Evidence for the phenol hydrate tautomers of 4-hydroxycyclohex-2-en-1-one metabolites was shown by formation of the corresponding trimethylsilyl ether derivatives. (Figure presented.).

Quinoides and VEGFR2 TKIs influence the fate of hepatocellular carcinoma and its cancer stem cells

Bioactivities of quinoides 1-5 and VEGFR2 TKIs 6-10 in hepatocellular cancer (HCC) and cancer stem cells (HCSCs) were studied. The compounds exhibited IC50 values in μM concentrations in HCC cells. Quinoide 3 was able to eradicate cancer stem cells, similar to the action of the stem cell inhibitor DAPT. However, the more cytotoxic VEFGR TKIs (IC50: 0.4-3.0 μM) including sorafenib, which is the only FDA approved drug for the treatment of HCC, enriched the hepatocellular cancer stem cell population by 2-3 fold after treatment. An aggressiveness factor (AF) was proposed to quantify the characteristics of drug candidates for their ability to eradicate the CSC subpopulation. Considering the tumour heterogeneity and marker positive cancer stem cell like subpopulation enrichment upon treatments in patients, this study emphasises the importance of the chemotherapeutic agent choice acting differentially on all the subpopulations including marker-positive CSCs.