Fusaric acid

Structural formula
General
Surname	Fusaric acid
other names	Fusaric acid; 5-butylpyridine-2-carboxylic acid; 5- n -butylpicolinic acid;
Molecular formula	C 10 H 13 NO 2
Brief description	colorless photosensitive crystals
External identifiers / databases
EC number	208-643-0
ECHA InfoCard	100,007,859
PubChem	3442
ChemSpider	3324
Wikidata	Q905703
properties
Molar mass	179.21 g · mol -1
Physical state	firmly
Melting point	108-109 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	180 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fusaric acid is a picolinic acid - derivative , as the secondary metabolite of the plant-damaging fungi of the genus Fusarium and the type Gibberella fujikuroi is formed.

Fusaric acid has herbicidal , insecticidal and antibacterial effects. It is a wilt toxin for plants (causes premature wilting), but it is only slightly toxic to the animal organism. It inhibits dopamine β-hydroxylase (an enzyme that converts dopamine to noradrenaline ), has antihypertensive activity and influences the membrane properties of cells. It works partially synergistically with other mycotoxins such. B. Deoxynivalenol (DON). Therefore, their role as a mycotoxin is not yet fully understood.

history

Fusaric acid was first identified in 1934 by Teijiro Yabuta at the University of Tokyo as a metabolite of the rice-damaging fungus Gibberella fujikuroi ( Fusarium moniliforme ).

Individual evidence

↑ ^a ^b entry on fusaric acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
↑ ^a ^b Fusaric acid data sheet from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).

↑ Entry on fusaric acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 7, 2020.

↑ T. Yabuta, K. Kambe, T. Hayashi (1937): Biochemistry of the bakanae fungus. I. Fusarinic acid, a new product of the bakanae fungus. In: J. Agric. Chem. Soc. Jpn. Vol. 10, pp. 1059-1068.

Web links

Detailed information on various mycotoxins

[Römpp-1] try on fusaric acid. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[sigma-2] Fusaric acid data sheet from Sigma-Aldrich , accessed on October 16, 2016 ( PDF ).

[ChemIDplus-3] Entry on fusaric acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 7, 2020.

[4] T. Yabuta, K. Kambe, T. Hayashi (1937): Biochemistry of the bakanae fungus. I. Fusarinic acid, a new product of the bakanae fungus. In: J. Agric. Chem. Soc. Jpn. Vol. 10, pp. 1059-1068.