2913-41-9

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethylis used as an intermediate in the synthesis of pharmaceutical compounds for its versatile chemical properties.
Used in Agricultural Industry:
This chemical compound is used in the agricultural industry for the synthesis of agrochemicals, contributing to the development of effective crop protection products.
Used in Dye and Pigment Production:
2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethylis utilized in the production of dyes and pigments due to its color-producing properties, enhancing the color range and quality of various products.
Used in Fragrance Industry:
It is employed as a building block in the synthesis of fragrances, contributing to the creation of unique and complex scents for various applications.
Used in Cosmetic and Personal Care Products:
2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethylhas potential applications in the cosmetic and personal care industry, where it can be used in the formulation of products to improve their performance and efficacy.

Upstream product

• 95-87-4 2,5-Dimethylphenol 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 40853-36-9 2,5-dimethyl-3,4-di-acetoxyphenyl acetate 
• 21390-25-0 1,3-dimethoxy-2,5-dimethylbenzene 
• 38790-14-6 1,2,5-trimethoxy-3-methylbenzene 
• 92421-46-0 3,6-dimethyl-1,2,4-trimethoxybenzene 
• 4179-19-5 1,3-dimethoxy-5-methylbenzene 
• 488-87-9 2,5-dimethyl-1,3-benzenediol 
• 110364-41-5 3-iodo-3,6-dimethyl-1,2-cyclohexanedione 
• 110364-43-7 4-iodo-3,6-dimethyl-1,2-benzenediol 
• 2748-08-5 2-hydroxy-3,6-dimethyl-2-cyclohexenone 
• 4380-95-4 2,5-dimethyl-1,3,4-trihydroxybenzene 

Downstream Products

• 2913-45-3 2-methoxy-3,6-dimethyl-1,4-benzoquinone 
• 29441-87-0 2-Azetidin-1-yl-5-hydroxy-3,6-dimethyl-[1,4]benzoquinone 
• 29441-86-9 2-hydroxy-5-(3-hydroxy-propylamino)-3,6-dimethyl-[1,4]benzoquinone 
• 29441-90-5 6,9-dimethyl-2,3,4,5-tetrahydro-benzo[b][1,4]oxazepine-7,8-dione 
• 29441-77-8 4,5,8-trimethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6,7-dione 
• 29441-85-8 2-hydroxy-5-(1-hydroxymethyl-propylamino)-3,6-dimethyl-[1,4]benzoquinone 
• 10493-51-3 4.4'-Dihydroxy-3.6.3'.6'-tetramethyl-biphenyldichinon 

Relevant academic research and scientific papers

Monocyclic Quinone Structure-Activity Patterns: Synthesis of Catalytic Inhibitors of Topoisomerase II with Potent Antiproliferative Activity

The monocyclic 1,4-benzoquinone, HU-331, the direct oxidation product of cannabidiol, inhibits the catalytic activity of topoisomerase II but without inducing DNA strand breaks or generating free radicals, and unlike many fused-ring quinones exhibits minimal cardiotoxicity. Thus, monocyclic quinones have potential as anticancer agents, and investigation of the structural origins of their biological activity is warranted. New syntheses of cannabidiol and (±)-HU-331 are here reported. Integrated synthetic protocols afforded a wide range of polysubstituted resorcinol derivatives; many of the corresponding novel 2-hydroxy-1,4-benzoquinone derivatives are potent inhibitors of the catalytic activity of topoisomerase II, some more so than HU-331, whose monoterpene unit replaced by a 3-cycloalkyl unit conferred increased antiproliferative properties in cell lines with IC50 values extending below 1 mM, and greater stability in solution than HU-331. The principal pharmacophore of quinones related to HU-331 was identified. Selected monocyclic quinones show potential for the development of new anticancer agents.

Total Synthesis of (?)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone

The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (?)-perezoperezone from commercially available 3,5-dimethoxytoluene.

Photoprocesses of p-Benzoquinones in Aqueous Solution

The photochemistry of 1,4-benzoquinone (BQ) and several derivatives, for example, duroquinone, trimethyl-2,5- or 2,6-dimethyl-, and methyl-BQ in aqueous solution or mixtures with polar media, for example, acetonitrile or 2,2,2-trifluoroethanol, was studied by time-resolved UV-vis spectroscopy after pulses at 248 and 308 nm. The triplet state and the semiquinone radical (?QH/Q?-) of BQs are spectroscopically and kinetically separated intermediates. The radical yield in the absence of H-atom donors is low and significantly increased in the presence of alcohols. Efficient photoinduced charge formation, because of Q?- and H+ after H-atom transfer from 2-propanol to the triplet state, and small effects in the absence of a donor were observed by transient conductivity. The quantum yield of photodecomposition, λirr = 254 nm, is substantial for BQ, MeBQ, and Me2BQs in aqueous solution, but small for Me 4BQ. To account for the efficient photoconversion of BQs into hydrobenzoquinones and 2-hydroxy-1,4-benzoquinones, a novel water-mediated reaction not involving free radicals is proposed as major step. This mechanism is consistent with the prediction that the observed triplet state is monomeric and the yield of Q?-, detected by both transient absorption and conductivity, is low for sub-millimolar BQ, MeBQ, and Me2BQs at pH 5-6. In addition, H-atom abstraction from a polar organic solvent or by self-quenching plays a role in mixtures with water or at enhanced quinone concentration, respectively.

A New Synthesis of 3-Hydroxy-2,5-dialkyl-1,4-benzoquinones Using Iodine-Copper(II) Acetate

Reactions of diosphenol and 3,6-dimethyl-1,2-cyclohexanedione with iodine-copper(II) acetate in acetic acid-water (5:1) at 80 deg C gave the respective 3-hydroxy-2,5-dialkyl-1,4-benzoquinone in 25-80 percent yields. 2-t-Butyl-5-methylcyclohexanone similar