2913-41-9

Basic information

• Product Name: 2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethyl-
• CAS NO: 2913-41-9
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Mol File: 2913-41-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethyl-(2913-41-9)
• EPA Substance Registry System: 2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethyl-(2913-41-9)

Safety Data

• Hazardous Substances Data: 2913-41-9(Hazardous Substances Data)

Usage

General Description

2,5-Cyclohexadiene-1,4-dione, 3-hydroxy-2,5-dimethyl- is a chemical compound that belongs to the family of cyclohexadiene-1,4-dione derivatives. It is also known as 3-hydroxy-2,5-dimethyl-p-benzoquinone and is commonly used in the synthesis of various organic compounds. This chemical is a yellow crystalline solid that is soluble in organic solvents. It is widely used in the pharmaceutical and agricultural industries, as well as in the production of dyes, pigments, and fragrances. Additionally, it has potential applications in the field of cosmetic and personal care products.

Upstream product

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

Downstream Products

• 29441-90-5 6,9-dimethyl-2,3,4,5-tetrahydro-benzo[b][1,4]oxazepine-7,8-dione 
• 29441-86-9 2-hydroxy-5-(3-hydroxy-propylamino)-3,6-dimethyl-[1,4]benzoquinone 
• 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 
• 29441-77-8 4,5,8-trimethyl-3,4-dihydro-2H-benzo[1,4]oxazine-6,7-dione 
• 29441-87-0 2-Azetidin-1-yl-5-hydroxy-3,6-dimethyl-[1,4]benzoquinone 
• 2913-45-3 2-methoxy-3,6-dimethyl-1,4-benzoquinone 

Relevant articles and documents

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.

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-benzoquinone from 3-halo-3,6-dialkyl-1,2-cyclohexanedione using iodine-copper(II) acetate

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