Terphenylquinones

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Terphenylquinones are fungal dyes from the group of phenyl-substituted p-benzoquinones having the following general structure. [1]

In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. Phenyl groups are closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and show nearly equal bond lengths between carbon atoms in the ring.

Contents

Terphenyl Quinones.svg

General chemical structure of terphenylquinones

Also derivatives with a central o-benzoquinone structure are known.

Biosynthesis

The biosynthesis of terphenylquinones is carried out by dimerization of substituted oxophenylpropanoic acids (phenylpyruvic acids).

Phenylpyruvic acid chemical compound

Phenylpyruvic acid is the organic compound with the formula C6H5CH2C(O)CO2H. It is a keto acid.

Occurrence

Terphenylquinones are typical constituents of the boletales.

Boletales Order of fungi

The Boletales are an order of Agaricomycetes containing over 1300 species with a diverse array of fruiting body types. The boletes are the best known members of this group, and until recently, the Boletales were thought to only contain boletes. The Boletales are now known to contain distinct groups of agarics, gasteromycetes, and other fruiting-body types.

Examples

BezeichnungStrukturCAS-Nr.Vorkommen
Polyporic acid Polyporic acid.svg 548-59-4Polypore of the order Aphyllophorales, Lichen Sticta coronata [2]
Atromentin Atromentin V2.svg 519-67-5Paxillus atrotomentosus (Basidiomycetes) [3]
Aurantiacin Aurantiacin.svg 548-32-3Hydnellum aurantiacum (Basidiomycetes) [4]
Phlebiarubron Phlebiarubron.svg 7204-23-1Cultures of Phlebia strigoso-zonata and Punctularia atropurpurascens (Basidiomycetes) [5]
Spiromentin B Spiromentin B.svg 121254-56-6Paxillus atrotomentosus (Basidiomycetes) and cultures of Paxillus panuoides [6]

See also

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References

  1. Burkhard Fugmann, ed. (1997), RÖMPP Lexikon Naturstoffe, 1. Auflage, 1997 (in German) (1. ed.), Stuttgart: Georg Thieme Verlag, p. 638, ISBN   3-13-749901-1
  2. Entry on Polyporsäure . at: Römpp Online . Georg Thieme Verlag, retrieved 3. September 2019.
  3. Entry on Atromentin . at: Römpp Online . Georg Thieme Verlag, retrieved 3. September 2019.
  4. Entry on Aurantiacin . at: Römpp Online . Georg Thieme Verlag, retrieved 3. September 2019.
  5. Entry on Phlebiarubron . at: Römpp Online . Georg Thieme Verlag, retrieved 3. September 2019.
  6. Entry on Spiromentine . at: Römpp Online . Georg Thieme Verlag, retrieved 3. September 2019.