Vulpinic acid

Structural formula
General
Surname	Vulpinic acid
other names	Letharic acid; ( E ) -2- (2,5-Dihydro-3-hydroxy-5-oxo-4-phenyl-2-furanylidene) -2-phenylacetic acid methyl ester; ( E ) -Methyl-2- (3,5-dioxo-4-phenyl-2-furylidene) -2-phenyl acetate ( IUPAC );
Molecular formula	C 19 H 14 O 5
Brief description	yellow crystals
External identifiers / databases
EC number	208-314-1
ECHA InfoCard	100.007.560
PubChem	54690323
Wikidata	Q411293
properties
Molar mass	322.33 g · mol -1
Physical state	firmly
Melting point	148-149 ° C
solubility	almost insoluble in water and ethanol ; readily soluble in diethyl ether and chloroform ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 260-280
Toxicological data	178 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vulpinic even Letharsäure , is an organic chemical compound belonging to the lactones , esters , enols and the group of pulvinic - dyes counts. Vulpinic acid is a powerful natural poison produced by some species of lichens, such as the wolf lichen ( Letharia vulpina ). It probably serves as a protection against snails from eating . As it is poisonous to all carnivorous vertebrates , it was previously used in Scandinavia to poison wolf and fox bait .

History and occurrence

Wolf lichen ( Letharia vulpina )

Vulpinic acid was discovered in 1831 when the French pharmacist and chemist Pierre-Antoine Bebert was studying lichen , but it was not until 1860 that it was examined and described in more detail by Franz Möller and Adolph Strecker . When longer heating the acid in aqueous barium hydroxide solution Möller and Strecker next received methanol and carbon dioxide a "methyl ether of oxalic acid , phthalic acid and benzoic acid ." Jacob Volhard was the first to synthesize vulpic acid and pulvic acid . Except in lichens, vulpinic acid is found in many mushrooms such as the thick bolete relatives as a yellow dye.

Chemical and biological properties

Vulpinic acid is not a carboxylic acid ; like ascorbic acid ( vitamin C ) , it has an enol grouping that has an acidic effect (also called " vinylogous carboxylic acid"). The alkoxides of vulpinic acid are formed in basic solutions, the ammonium , alkali and alkaline earth salts (with the exception of the potassium salt) being readily soluble, the compounds of all other metals being sparingly soluble in water. The saponification of vulpinic acid produces the carboxylic acid pulvic acid .

Vulpinic acid, like abscisic acid, is a natural growth inhibitor in plants and has anti-inflammatory and antibacterial effects in humans .

Web links

Wiktionary: vulpinic acid - explanations of meanings, word origins, synonyms, translations

Individual evidence

↑ ^a ^b ^c ^d Entry on vulpinic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ External identifiers of or database links to methyl 2- (5-hydroxy-3-oxo-4-phenylfuran-2-ylidene) -2-phenylacetic acid : CAS number: 73622-57-8, PubChem : 54684634 , Wikidata : Q69892092 .
↑ ^a ^b extrasynthesis: Vulpic acid , accessed December 27, 2019.
↑ Entry on vulpinic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ ^A ^b Canstatt's Annual Report on Advances in Pharmacy and Allied Sciences in All Countries , Harvard University, Volume 10 (1861).
^ Robert L. Frank, George R. Clark, James N. Coker: The Synthesis of Vulpinic Acid from Polyporic Acid . In: J. Am. Chem. Soc. , 1950, 72 , pp. 1824-1826; doi : 10.1021 / ja01160a121 .

[Römpp-1] Entry on vulpinic acid. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[2] External identifiers of or database links to methyl 2- (5-hydroxy-3-oxo-4-phenylfuran-2-ylidene) -2-phenylacetic acid : CAS number: 73622-57-8, PubChem : 54684634 , Wikidata : Q69892092 .

[extrasynthese-3] xtrasynthesis: Vulpic acid , accessed December 27, 2019.

[ChemIDplus-4] Entry on vulpinic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[canstatt-5] A ^b Canstatt's Annual Report on Advances in Pharmacy and Allied Sciences in All Countries , Harvard University, Volume 10 (1861).

[6] Robert L. Frank, George R. Clark, James N. Coker: The Synthesis of Vulpinic Acid from Polyporic Acid . In: J. Am. Chem. Soc. , 1950, 72 , pp. 1824-1826; doi : 10.1021 / ja01160a121 .