3214-57-1

Usage

Physical state

Yellow crystalline solid

Odor

Distinct

Solubility

Insoluble in water

Uses

Synthesis of pharmaceuticals and organic compounds; antioxidant properties in skincare and cosmetic products; intermediate in the production of various chemical compounds

Potential applications

Organic chemistry research and development

Upstream product

• 2913-40-8 3,5-dimethyl-2-hydroxy-p-benzoquinone 
• 77-78-1 dimethyl sulfate 
• 2785-85-5 2-methoxy-3,5-dimethylphenol 
• 29769-77-5 3-methoxy-4-methyl-3-cyclobutene-1,2-dione 
• 74-99-7 prop-1-yne 
• 92421-42-6 1,3-dimethyl-2,4,5-trimethoxybenzene 
• 41168-76-7 1,3-dimethyl-2,4,5-triacetoxybenzene 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 

Downstream Products

• 1431987-13-1 6-(5-methoxy-2,4-dimethyl-3,6-dioxo cyclohexa-1,4-dienyl)hexyl nitrate 
• 1431987-16-4 10-(5-methoxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienyl)decyl nitrate 
• 1431987-18-6 8-(5-methoxy-2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienyl)octyl nitrate 

Relevant academic research and scientific papers

QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS FOR OPHTHALMIC USE

The present invention relates to novel nitric oxide donor compounds for the use in the treatment and/or prophylaxis of hypertensive glaucoma, normotensive glaucoma and ocular hypertension.

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 of pathological conditions where a deficit of NO plays an important role in their pathogenesis.

Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria

Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate.

Reductive Lactonization of Strategically Methylated Quinone Propionic Acid Esters and Amides

It has been shown that the reduction of quinone propionic acid esters or amides bearing three methyl groups in the so-called "trialkyl lock" positions (o-, β-, β-positions) is accompanied by spontaneous lactonization with the release of alcohol or amine, respectively.A new convenient method is reported for introducing the β,β-dimethylpropionic acid side chain onto an appropriate hydroquinone nucleus via alkylative cyclization in methanesulfonic acid.Oxidation of the resulting lactone gives the quinone propionic acid, which can be converted by normal techniques to the corresponding ester or amide derivative.Initial model studies were carried out on pentamethylated systems 6 and 7.In order to make available quinones of varying redox potential or enhanced solubility in physiological media, methoxy- and amino-substituted quinones 10a, 10b, and 17a,b were synthesized.Upon reduction under mild conditions (Na2S2O4), all model esters or amides underwent reductive cyclization with loss of alcohol or amine.In the case of 7a the intermediate hydroquinone 19 could be isolated and its conversion to 4 with ejection of diethylamine followed by NMR techniques