2,5-Dimethylhydroquinone

CAS

615-90-7

Catalog Number

ACM615907

Category

Main Products

Molecular Weight

138.16

Molecular Formula

C8H10O2

MSDS COA Spec Sheet

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Specification

Synonyms

2,5-dimethylbenzene-1,4-diol

Appearance

White solid

Kinetic study of the reaction of 2,5-dimethylhydroquinone with imines

Dependence of the initial rate of reaction(wQMI) on the rate of initiation

Antonov, A. V., and V. T. Varlamov. Kinetics and catalysis 47 (2006): 524-532.

The kinetics of the reaction of N-phenyl-1,4-benzoquinone monoimine with 2,5-dimethylhydroquinone in chlorobenzene at 298.2 and 340 K were studied. The reaction occurs via a chain mechanism with a chain length of about 10-10 units, depending on temperature and reactant concentrations. The reaction orders and rate constants for all elementary steps at 298.2 and 340 K were determined. The experimental data were compared with previously obtained results for the reaction of N-phenyl-1,4-benzoquinone monoimine with 2,5-di-tert-butyl-1,4-hydroquinone. The nature of the substituents in hydroquinone has a strong influence on the kinetic parameters of this novel class of chain reactions. The effect of the final product 2,5-dimethylquinone on the reaction kinetics at 298.2 and 340 K was studied, and it was found that the 2,5-dimethylquinone additive has only a weak inhibitory effect.
The reaction occurs by a mechanism similar to that proposed previously for the reaction of QMI with 2,5-di-tert-butylhydroquinone. Despite the similar nature of the methyl and tert-butyl substituents and the identical position of the substituents in the benzene ring of hydroquinone, the kinetics of the two tested reactions differ significantly. Thus, the rate constants of the elementary steps (1) and (3) in both reactions are close to each other, while the rate constant of step (2) differs by almost an order of magnitude. The chain reaction kinetics between quinone imines and hydroquinones can therefore serve as a sensitive method to investigate the influence of the nature of the substituents on the reactivity of hydroquinones and their semiquinone radicals as H-atom donors. In this work, the influence of the final product 2,5-dimethylquinone on the kinetics of the reaction of Ar(OH) with QMI was investigated for the first time and an inhibitory effect of this product was found, which can be explained by the reversibility of the elementary step in the formation of quinone Q.

Biological Evaluation of 2,5-Dimethylhydroquinone, a Metabolite of Benzoquinone Biotransformation

Microbial transformation result of 2,5-dimethyl-1,4-benzoquinone (DMBQ)

Ağalar, Hale Gamze, et al. Natural Volatiles and Essential Oils 4.1 (2017): 14-17.

2,5-Dimethyl-1,4-benzoquinone (DMBQ) is one of the naturally occurring quinones found as a defense metabolite in insects. DMBQ was biotransformed by the microfungus Corynespora cassicola. The transformation metabolite 2,5-Dimethylhydroquinone was initially screened by TLC and GC-MS and then further characterized by NMR (13C and 1H-NMR) spectroscopic techniques. In addition, the in vitro anti-Candida, antioxidant properties, and XTT cytotoxicity of the substrate and metabolites were evaluated.
Serial dilutions were performed from the stock solutions of 2,5-Dimethylhydroquinone and 2,5-Dimethyl-1,4-benzoquinone samples (10 mg/mL) to obtain concentrations of 10, 5, 2.5 x 10, 1.25 x 10, 62.5 x 10, 31.25 x 10mg/mL. UV absorbance was recorded at 517 nm. The experiment was performed in triplicate and the average absorbance of each concentration was recorded. The same procedure was followed for the positive control gallic acid.
For XTT assay, WSI human skin fibroblast cell line was used to study the cytotoxicity of the compounds. Cells were incubated at 37°C in a humidified atmosphere of 95% air and 5% CO. WSI cells were seeded at 1x10 cells per well of a 96-well plate. After 24 h of incubation, compounds ranging in concentration from 3.9500 μg/mL were added to the wells in quadruplicate. After 24 h of incubation with the compounds, XTT assay was performed according to the manufacturer's instructions. The absorbance was measured using a microplate reader at 480 nm with a reference wavelength of 680 nm after 2 h of incubation. The % inhibition for each compound concentration was calculated according to the manufacturer's instructions and the IC50 values were estimated by plotting a dose-response curve of % inhibition versus the concentration of the test compound. Stock solutions of compounds were prepared in DMSO and further diluted in fresh medium. Final DMSO concentration was less than 0.1%. All data are from 3 independent experiments performed in quadruplicate.

What is the molecular formula of 2,5-Dimethylhydroquinone?

The molecular formula of 2,5-Dimethylhydroquinone is C8H10O2.

What are the synonyms for 2,5-Dimethylhydroquinone?

The synonyms for 2,5-Dimethylhydroquinone are 2,5-dimethylbenzene-1,4-diol and 1,4-Benzenediol, 2,5-dimethyl-.

What is the molecular weight of 2,5-Dimethylhydroquinone?

The molecular weight of 2,5-Dimethylhydroquinone is 138.16 g/mol.

When was 2,5-Dimethylhydroquinone created and modified?

2,5-Dimethylhydroquinone was created on 2005-03-26 and last modified on 2023-10-21.

What is the IUPAC name of 2,5-Dimethylhydroquinone?

The IUPAC name of 2,5-Dimethylhydroquinone is 2,5-dimethylbenzene-1,4-diol.

What is the InChI of 2,5-Dimethylhydroquinone?

The InChI of 2,5-Dimethylhydroquinone is InChI=1S/C8H10O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4,9-10H,1-2H3.