1,4-Benzoquinone

• P- Benzoquinone
• P-quinone
• Cyclohexa -2 ,5-diene -1 ,4 -dione

Tan solid with a pungent odor

Fixed

1.32 g · cm -3

116 ° C.

12 Pa ( 20 ° C)

Poorly in water (10 g · l-1 at 20 ° C)

Risk

Not classified as carcinogenic effect

Template: Infobox chemical / molecular formula search available

1,4- benzoquinone, often simply called quinone or benzoquinone, is the trunk of the body (para) - quinones. It forms yellow crystals with a characteristic, penetrating odor. 1,4- benzoquinone is formed in the oxidation of hydroquinone and as a metabolite in humans with benzene poisoning.

History

In studies on the chemistry of isolated from cinchona Chinasäure watched the Russian chemist Alexander Abramovich Voskresensky that in the oxidation with manganese dioxide ( pyrolusite ) is formed in sulfuric acid a yellow, pungent-smelling substance to which he gave the name " quinoyl ".

Since the ending- yl should represent a radical ( radical), named Friedrich Wohler the connection into " Chinon ".

Production and representation

The oxidation of hydroquinone in sulfuric acid solution with sodium chlorate ( and vanadium pentoxide as a catalyst) or with sodium dichromate is possible with high yield.

Biological Significance

P- benzoquinone is harmful to blood and is suspected to cause leukemia. It reacts rapidly with biological macromolecules such as proteins and DNA. The adduct with albumin can be detected in broad sectors of the population, and these biomarkers for Chinon ( and thus also for benzene ) correlated with automobile refueling, cigarette consumption, but also with fruit consumption and use of aspartame. The defense for the serving of predators defensive secretions of bombardier beetles contains 1,4- benzoquinone. Bombardier beetles and harvestmen have the ability to produce in glands 1,4-benzoquinone.

Also, some types of centipedes make benzoquinone ago to ward off predators. In Madagascar, and in South America an unusual observation could be made in this context: Malagasy lemurs and South American capuchin monkey catch and irritate the centipede so that they secrete their benzochinonhaltiges secretion. This distribute the monkeys turn on their fur, where it exerts its insect repellent effect and particular, protects against disease-carrying mosquitoes and mosquitoes. The primates take on the psychoactive effects of the secretion apparently benevolent in purchasing. A selective advantage does not come here sooner, as the risk of being eaten during the 20 minute drug intoxication, is significantly increased. It is therefore to be assumed that the elicitation of a rush in the foreground.