Phenanthrenedione is a quinone derivative of a

polycyclic aromatic hydrocarbon A Polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter— by engine exhaust fumes, tobacco, incine ...

. It is an orange, water-insoluble solid.

Laboratory synthesis and use

It has been prepared by oxidation of

phenanthrene Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics, pesticides, expl ...

with

chromic acid Chromic acid is a chemical compound with the chemical formula . It is also a jargon for a solution formed by the addition of sulfuric acid to aqueous solutions of dichromate. It consists at least in part of chromium trioxide. The term "chromic ...

. It is used as an artificial mediator for electron acceptor/donor in Mo/W containing

formate dehydrogenase Formate dehydrogenases are a set of enzymes that catalyse the oxidation of formate to carbon dioxide, donating the electrons to a second substrate, such as NAD+ in formate:NAD+ oxidoreductase () or to a cytochrome in formate:ferricytochrome-b1 o ...

reduction of carbon dioxide to formate and vice versa. It is a better electron acceptor than the natural

nicotinamide adenine dinucleotide Nicotinamide adenine dinucleotide (NAD) is a Cofactor (biochemistry), coenzyme central to metabolism. Found in all living cell (biology), cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphat ...

(NAD⁺).

Safety

It is

cytotoxic Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of dr ...

and potentially mutagenic. Phenanthrenequinone is one of many contributors to harmful particulate emissions from diesel motor vehicles.

Related compounds

1,10-Phenanthroline-5,6-dione 1,10-Phenanthroline-5,6-dione is an organic compound with the formula . It is the quinone derivative of 1,10-phenanthroline. The compound exhibits many reactions, including condensations with diamines to give quinoxalines and decarbonylation to ...

References

Quinones Phenanthrenes {{organic-compound-stub