3066-90-8

Basic information

• Product Name: 2,3-Dimethoxy-5-methyl-1,4-hydroquinone
• Synonyms: 1,4-DIHYDROXY-2,3-DIMETHOXY-5-METHYLBENZENE;2,3-DIMETHOXY-5-METHYL-BENZENE-1,4-DIOL;2,3-DIMETHOXY-5-METHYLHYDROQUINONE;2,3-DIMETHOXY-5-METHYL-BENZENE-1,4-DIOL (2,3-DIMETHOXY-5-METHYLHYDROQUINONE);2 3-DIMETHOXY-5-METHYLHYDROQUINONE 98%;2,3-Dimethoxy-5-methyl-1,4-hydroquinone;2,3-Dimethoxy-5-methyl-1,4-benzenediol;2,3-Dimethoxy-6-methylhydroquinone
• CAS NO: 3066-90-8
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 3066-90-8.mol
• Article Data: 38

Chemical Properties

• Melting Point: 74.5-75.5 °C
• Boiling Point: 340.3 °C at 760 mmHg
• Flash Point: 159.6 °C
• Appearance: /
• Density: 1.223 g/cm³
• Vapor Pressure: 4.39E-05mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.45±0.28(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 2,3-Dimethoxy-5-methyl-1,4-hydroquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethoxy-5-methyl-1,4-hydroquinone(3066-90-8)
• EPA Substance Registry System: 2,3-Dimethoxy-5-methyl-1,4-hydroquinone(3066-90-8)

Safety Data

• Hazardous Substances Data: 3066-90-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dimethoxy-5-methyl-1,4-hydroquinone is used as a pharmaceutical agent for its antioxidant and free radical scavenging properties. It serves to protect cells from oxidative stress and DNA damage, which are common issues in various diseases and conditions.
Used in Cosmetic Industry:
In the cosmetic industry, 2,3-Dimethoxy-5-methyl-1,4-hydroquinone is used as an ingredient in skincare products for its antioxidant properties. It helps to neutralize free radicals that can cause skin damage and premature aging, promoting a healthier and more youthful appearance.
Used in Research Applications:
2,3-Dimethoxy-5-methyl-1,4-hydroquinone is used as a research compound for studying the effects of antioxidants and free radical scavengers on cellular processes and the potential for developing new therapeutic strategies against various diseases, including those related to oxidative stress and DNA damage.
Used in Chemical Synthesis:
2,3-Dimethoxy-5-methyl-1,4-hydroquinone is also used as a starting material or intermediate in the synthesis of more complex organic molecules, particularly in the fields of pharmaceuticals and materials science, where its unique structure and properties can be exploited to create novel compounds with specific applications.

InChI:InChI=1/C9H12O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4,10-11H,1-3H3

Upstream product

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Downstream Products

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• 7704-04-3 2-geranyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone 
• 51077-59-9 Phytyl-ubichinon (2.3-Dimethoxy-5-methyl-6-phytyl-1.4-benzochinon) 
• 35896-58-3 2,3,4,5-tetramethoxytoluene 
• 22028-20-2 1,4-diacetoxy-2,3-dimethoxy-5-methylbenzene 

Relevant articles and documents

The Trapping of the OH Radical by Coenzyme Q. A Theoretical and Experimental Study

Several pathways for the attack of the hydroxyl radical on coenzyme Q, as a prototypical chemical reaction involved in biological antioxidant actions, were theoretically analyzed by hybrid density functional theory computations, at the BHandHLYP/6-31G level. We found that the most favorable pathways are the hydrogen abstraction reaction from the phenolic hydrogen on the reduced form (ubiquinol), and the electrophilic OH addition on the oxidized form (ubiquinone). The reaction paths for the two mechanisms were traced independently. Following the direct dynamics method, the respective thermal rate constants were calculated using variational transition-state theory with multidimensional small-curvature tunneling. The experimental rate constants for the reaction of ubiquinol and ubiquinone with hydroxyl radicals produced via the Fenton's reaction in phosphate-buffered water solution at pH 7 were also measured. We found, first, that the reactivity in gas-phase (theoretical approach) is dominated by the OH addition mechanism on ubiquinone, and second, that a good agreement exists between the ratio of the rate constants determined from theoretical and experimental approaches for the reaction of oxidized and reduced forms of coenzyme Q with hydroxyl radicals. It is a very fast reaction, practically diffusion-controlled, with an inverse dependence of the thermal rate constants on temperature and therefore, a negative activation energy, both theoretically and experimentally. The influence of the tunneling factor was negligible. The analysis of the enthalpy and entropy contributions to the Gibbs free energy profile allowed us to understand the negative value of the activation energy.

Catalytic formation of hydrogen peroxide from coenzyme NADH and dioxygen with a water-soluble iridium complex and a ubiquinone coenzyme analogue

A ubiquinone coenzyme analogue (Q0: 2,3-dimethoxy-5-methyl-1,4-benzoquinone) was reduced by coenzyme NADH to yield the corresponding reduced form of Q0 (Q0H2) in the presence of a catalytic amount of a [C,N] cyclometalated organoiridium complex (1: [IrIII(Cp?)(4-(1H-pyrazol-1-yl-κN2)benzoic acid-κC3)(H2O)]2SO4) in water at ambient temperature as observed in the respiratory chain complex I (Complex I). In the catalytic cycle, the reduction of 1 by NADH produces the corresponding iridium hydride complex that in turn reduces Q0 to produce Q0H2. Q0H2 reduced dioxygen to yield hydrogen peroxide (H2O2) under slightly basic conditions. Catalytic generation of H2O2 was made possible in the reaction of O2 with NADH as the functional expression of NADH oxidase in white blood cells utilizing the redox cycle of Q0 as well as 1 for the first time in a nonenzymatic homogeneous reaction system.

A ubiquinol-based charge-transfer complex obtained from a solvent-free approach

Quinones (=cyclohexa-2,5-diene-1,4-diones) and hydroquinones (=benzene-1,4-diols) belong to species that are balanced between their redox character and their ability to build supramolecular complexes. Considering the ubiquinol 2,3-dimethoxy-5-methyl-1,4-dihydroquinone (=2,3-dimethoxy-5- methylbenzene-1,4-diol; 1), the tendency to undergo an oxidation side reaction was overcome by combining this electron-donating species 1 with a nonreactive partner, benzene-1,2,4,5-tetracarbonitrile (TCNB; 3), to yield a 2 : 1 charge-transfer (CT) complex 4. This work illustrates how very convenient the solvent-free techniques are to access intermolecular species. X-Ray diffraction studies revealed that pure ubiquinol 1 (structure included) crystallizes in two enantiomeric conformations, while the triads 4 formed with TCNB (3) exist as meso forms assembled via H-bonds in zigzag-chains patterns.

Superoxide Dismutase Inhibition of Oxidation of Ubiquinol and Concomitant Formation of Hydrogen Peroxide

We measured ubiquinone (CoQ0) and hydrogen peroxide (H2O2) formed in the process of oxidation of ubiquinol (CoQ0H2). We found that copper-zinc superoxide dismutase and manganese superoxide dismutase inhibited both the CoQ0 formation and the H2O2 formation only in the presence of chelators such as DTPA (diethylenetriaminepentaacetic acid). The amount of H2O2 was almost equal to that of CoQ0, indicating that the H2O2 formation was coupled with the CoQ0 formation. The lack of inhibitory effects of the corresponding heat-inactivated superoxide dismutase (SOD) confirmed that the inhibition by the original SOD was due to its enzymatic activity. We propose that CoQ0H2 oxidation occurs as a chain reaction with superoxide as the chain carrier and that SOD inhibits this reaction by lowering the superoxide concentration.

SPERMINE PRO-DRUGS

Disclosed herein are novel spermine prodrugs and methods of use for treating subjects exhibiting symptoms of a low spermine disorder. Also disclosed are methods of synthesizing spermine prodrugs. Compositions containing spermine prodrugs are also disclosed.

Development of a Redox-Sensitive Spermine Prodrug for the Potential Treatment of Snyder Robinson Syndrome

Snyder Robinson Syndrome (SRS) is a rare disease associated with a defective spermine synthase gene and low intracellular spermine levels. In this study, a spermine replacement therapy was developed using a spermine prodrug that enters cells via the polyamine transport system. The prodrug was comprised of three components: a redox-sensitive quinone "trigger", a "trimethyl lock (TML)"aryl "release mechanism", and spermine. The presence of spermine in the design facilitated uptake by the polyamine transport system. The quinone-TML motifs provided a redox-sensitive agent, which upon intracellular reduction generated a hydroquinone, which underwent intramolecular cyclization to release free spermine and a lactone byproduct. Rewardingly, most SRS fibroblasts treated with the prodrug revealed a significant increase in intracellular spermine. Administering the spermine prodrug through feeding in a Drosophila model of SRS showed significant beneficial effects. In summary, a spermine prodrug is developed and provides a lead compound for future spermine replacement therapy experiments.

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water

A series of unsaturated carbonyls, quinones, and pyridinium salts have been effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes, and hydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient, and metal-free reduction system. Deuterium-labeling experiments have revealed this protocol to be an exclusive transfer hydrogenation process from water. This journal is

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

Catalytic Electrophilic Alkylation of p-Quinones through a Redox Chain Reaction

Allylation and benzylation of p-quinones was achieved through an unusual redox chain reaction. Mechanistic studies suggest that the existence of trace hydroquinone initiates a redox chain reaction that consists of a Lewis acid catalyzed Friedel–Crafts alkylation and a subsequent redox equilibrium that regenerates hydroquinone. The electrophiles could be various allylic and benzylic esters. The addition of Hantzsch ester as an initiator improves the efficiency of the reaction.

QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS

The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment and/or prophylaxis of glaucoma and ocular hypertension.