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1,4-Benzoquinone is prepared industrially by oxidation of hydroquinone, which can be obtained by several routes. One route involves oxidation of diisopropylbenzene and the Hock rearrangement. The net reaction can be represented as follows: C 6 H 4 (CHMe 2) 2 + 3 O 2 → C 6 H 4 O 2 + 2 OCMe 2 + H 2 O
Hydroquinone can be reversibly oxidised under mild conditions to give benzoquinone. Naturally occurring hydroquinone derivatives, such as coenzyme Q, exhibit similar reactivity, wherein one hydroxyl group is exchanged for an amino group. Given the conditional reversibility and relative ubiquity of reagents, oxidation reactions of hydroquinones ...
The auto-oxidation of the neurotransmitter dopamine and its precursor L-Dopa generates the comparatively stable dopamine quinone which inhibits the functioning of dopamine transporter (DAT) and the TH enzyme and leads to low mitochondrial ATP production. [15] The benzoquinone blattellaquinone is a sex pheromone in cockroaches.
The loss of nutrients can occur due to the interaction of quinones, produced by the oxidation of diphenols, with the side chains of essential amino acids derived from plant proteins. In particular, thiol and amine functional groups on the side chains of amino acids are highly susceptible to quinone binding and alkylation. [18]
A general observation is that there is high variation in the extent of damage due to benzene poisoning. A possible explanation is the accumulation of phenols and hydroquinone in the target organ—the bone marrow—and subsequent oxidation of these metabolites to reactive quinone metabolites via a number of possible pathways. [11]
The Q cycle (named for quinol) describes a series of sequential oxidation and reduction of the lipophilic electron carrier Coenzyme Q (CoQ) between the ubiquinol and ubiquinone forms. These reactions can result in the net movement of protons across a lipid bilayer (in the case of the mitochondria, the inner mitochondrial membrane).
Resonance structures of a semiquinone. Semiquinones (or ubisemiquinones, if their origin is ubiquinone) are free radicals resulting from the removal of one hydrogen atom with its electron during the process of dehydrogenation of a hydroquinone, such as hydroquinone itself or catechol, to a quinone or alternatively the addition of a single hydrogen atom with its electron to a quinone. [1]
Benzoquinone (C 6 H 4 O 2) is a quinone with a single benzene ring. There are 2 (out of 3 hypothetical) benzoquinones: 1,4-Benzoquinone, most commonly, right image (also para-benzoquinone, p-benzoquinone, para-quinone, or just quinone) 1,2-Benzoquinone, less commonly, left image (also ortho-benzoquinone, o-benzoquinone, ortho-quinone)