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Vulpinic acid

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Vulpinic acid
Chemical structure of vulpinic acid
Chemical structure of vulpinic acid
File:Vulpinic acid.jpg
Names
IUPAC name Methyl (2E)-2-(5-hydroxy-3-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.007.560 Edit this at Wikidata
PubChem CID
SMILES
  • COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3
Properties
Chemical formula C19H14O5
Molar mass 322.316 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Vulpinic acid is a naturally occurring pulvinic acid derivative found in several lichen species, as well as some non-lichenized fungi. It was first isolated in 1925. It is bright yellow, and relatively toxic.

Occurrence in Lichen

Together with usnic acid and pinastric acid, vulpinic acid is secondary metabolite of the fungi. It is speculated that the substances are used as repellent for some herbivores. The substance showed also some activity against gram-positive bacteria.

References

  1. Mazza, Franc Paolo (1925). "Constitution and physical properties of vulpinic acid". Rend. Accad. Sci. Napoli. 31: 182–90.
  2. Lawrey, James D. (1989). "Lichen Secondary Compounds: Evidence for a Correspondence between Antiherbivore and Antimicrobial Function". The Bryologist. 92 (3). The Bryologist, Vol. 92, No. 3: 326–328. doi:10.2307/3243401.
  3. Bačkor, M.; Hudá, J.; Repčák, M.; Ziegler§, W.; Bačkorová, M. (1998). "The Influence of pH and Lichen Metabolites (Vulpinic Acid and (+) Usnic Acid) on the Growth of the Lichen Photobiont Trebouxia Irregularis". The Lichenologist. 30: 577. doi:10.1017/S0024282992000574.


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