Phenanthrenequinone Explained

Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.

Laboratory synthesis and use

It has been prepared by oxidation of phenanthrene with chromic acid.^[1]

It is used as an artificial mediator for electron acceptor/donor in Mo/W containing formate dehydrogenase reduction of carbon dioxide to formate and vice versa. It is a better electron acceptor than the natural nicotinamide adenine dinucleotide (NAD⁺).

Safety

It is cytotoxic^[2] and potentially mutagenic.^[3]

Phenanthrenequinone is one of many contributors to harmful particulate emissions from diesel motor vehicles.^[4]

Related compounds

• 1,10-Phenanthroline-5,6-dione

Notes and References

1. Phenanthrenequinone. Ray. Wendland. John. LaLonde. Org. Synth.. 1954. 34. 76. 10.15227/orgsyn.034.0076.
2. Robert A. Kanaly. Natsuko Hamamura. 9,10-Phenanthrenedione biodegradation by a soil bacterium and identification of transformation products by LC/ESI-MS/MS. Chemosphere. September 2013. 92. 11. 1442–1449. 10.1016/j.chemosphere.2013.03.054. 23611246. 2013Chmsp..92.1442K.
3. 10.1016/s0165-1218(96)90103-2 . Human cell mutagenicity of oxygenated, nitrated and unsubstituted polycyclic aromatic hydrocarbons associated with urban aerosols . 1996 . Durant . John L. . Busby . William F. . Lafleur . Arthur L. . Penman . Bruce W. . Crespi . Charles L. . Mutation Research/Genetic Toxicology . 371 . 3–4 . 123–157 . 9008716 .
4. 10.1021/es00041a007 . Sources of fine organic aerosol. 2. Noncatalyst and catalyst-equipped automobiles and heavy-duty diesel trucks . 1993 . Rogge . Wolfgang F. . Hildemann . Lynn M. . Mazurek . Monica A. . Cass . Glen R. . Simoneit . Bernd R. T. . Environmental Science & Technology . 27 . 4 . 636–651 .