Vulpinic acid

Names

IUPAC name

Methyl (2E)-2-(5-hydroxy-3-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate

Identifiers

CAS Number

521-52-8^Y

3D model (Jmol)

Interactive image

ECHA InfoCard

100.007.560

PubChem CID

3033539

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

322.32 g·mol⁻¹

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

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.

Vulpinic acid was first isolated from lichens, and is a secondary metabolite of the fungal partner. It is speculated that vulpinic acid's biological function is as a repellent for some herbivores. Humans have also exploited this toxicity by using lichens that contain high amounts of the chemical (such as Letharia vulpina) as poison for wolves and foxes. The substance showed also some antibacterial activity against gram-positive bacteria and has even been shown to disrupt cell division in MRSA.

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