Vulpinic acid
From Wikipedia, the free encyclopedia
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| Names | |||
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| Preferred IUPAC name
Methyl (E)-(5-hydroxy-3-oxo-4-phenylfuran-2(3H)-ylidene)phenylacetate | |||
| Identifiers | |||
3D model (JSmol) |
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| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.007.560 | ||
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PubChem CID |
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| Properties | |||
| C19H14O5 | |||
| Molar mass | 322.316 g·mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H302 | |||
| P264, P270, P301+P317, P330, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Vulpinic acid is a natural product first found in and important in the symbiosis underlying the biology of lichens.[1] It is a simple methyl ester derivative of its parent compound, pulvinic acid, and a close relative of pulvinone, both of which derive from aromatic amino acids such as phenylalanine via secondary metabolism. The roles of vulpinic acid are not fully established, but may include properties that make it an antifeedant for herbivores. The compound is relatively toxic to mammals.
Vulpinic acid was first isolated from lichens in 1925.[2][non-primary source needed] As an isolated, purified substance, it is bright yellow in color.[3]
Vulpinic acid is derived biosynthetically by esterification from pulvinic acid;[4] pulvinate itself derives from the aromatic amino acids phenylalanine and tyrosine, via dimerization and oxidative ring-cleavage of arylpyruvic acids, a process that also produces the related pulvinones.[5][page range too broad]
There have been several chemical syntheses reported for vulpinic acid. In one, butenolides were efficiently functionalized by Suzuki cross-coupling reactions via the corresponding enol triflates[further explanation needed].[6]
Occurrence in lichens
Pulvinic acid is found in several lichen species, as well as some non-lichenized fungi.[2][better source needed] It is a secondary metabolite of the fungal partner in the lichen symbiosis.[citation needed] It was found in the bolete fungus Pulveroboletus ravenelii.[7][5] In 2016, a new group of basidiomycetes distinct from the well known lichen fungal partner was implicated in producing vulpinic acid.[1]