Pulvinic acid

3,4-dihydroxy- 2 ,5 -diphenyl -2 ,4- Hexadiendisäure gamma-lactone

Orange prisms

Fixed

216-217 ° C ( decomposition)

6.86 ± 0.05

• Soluble in ethanol
• Poorly in water and diethyl ether

• 500 mg · kg -1 ( LD50, mouse, ip)
• 1,000 mg · kg -1 ( LD50, mouse, oral)

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The Pulvinsäure is an organic chemical compound (also alkenoic ) is one of the lactones, enols and unsaturated carboxylic acids. They were widespread in fungi and lichens group of Pulvinsäure dyes her name. Compared to its methyl ester Vulpinsäure the Pulvinsäure has a much lower toxicity.

History and habitat

In fungi and lichens Dickröhrlingsverwandten as the many different dyes are present which are either derivatives of Pulvinsäure (about Gomphidsäure ) or composed of a plurality Pulvinsäure - units ( for example, two units: Badione ). 1831 Pulvinsäure - Methlyester Vulpinsäure was discovered in the study of lichens by the French pharmacist and chemist Antoine Bebert, but in 1860 examined more closely by Franz Möller and Adolph Strecker and described.

Representation and biosynthesis

Jacob Volhard synthesized as the first Vulpinsäure and Pulvinsäure. In fungi, the biosynthesis via tyrosine or phenylalanine runs; it is produced by deamination, dimerization and ring cleavage finally Pulvinsäure or Hydroxypulvinsäure.

Chemical Properties

Pulvinsäure is a lactone, so an intramolecular ester of trans-1 ,4 -diphenyl- 2 ,3- dihydroxy- 1 ,3-butadiene -1 ,4 -dicarboxylic acid and is produced from this by elimination of water: The occurring in many Dickröhrlingsverwandten Hydroxypulvinsäuren Xerocomsäure and Variegatsäure are the cause of the blue color of the fruit body with pressure or injury by being oxidized to quinones blue.

Biological Significance

Many yellow dyes in fungi and lichens are derived from the Pulvinsäure. A distinction is made between derivatives of Pulvinsäure and di - and oligomeric substances. The dimers include the Badione; Derivatives of the monomer are about the Gomphidsäure and Vulpinsäure. The Vulpinsäure, the methyl ester of Pulvinsäure, is a strong poison that serves the producing fungi and lichens as corrosion protection from snails and other predators.