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F6513

Sigma-Aldrich

Fusaric acid

from Gibberella fujikuroi

Synonym(s):

5-Butylpicolinic acid, 5-Butylpyridine-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H13NO2
CAS Number:
536-69-6
Molecular Weight:
179.22
Beilstein/REAXYS Number:
125804
EC Number:
208-643-0
MDL number:
MFCD00006298
UNSPSC Code:
12352106
PubChem Substance ID:
24278183
NACRES:
NA.77

biological source

Gibberella fujikuroi

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

95-97  °C

solubility

ethanol: 49.00-51.00 mg/mL, clear, colorless to faintly yellow

antibiotic activity spectrum

Gram-positive bacteria

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CCCCc1ccc(nc1)C(O)=O

InChI

1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13)

InChI key

DGMPVYSXXIOGJY-UHFFFAOYSA-N

Gene Information

human ... DBH(1621)

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General description

Chemical structure: pyridine

Biochem/physiol Actions

Dopamine β-hydroxylase inhibitor.

Features and Benefits

This compound is featured on the Dopamine, Norepinephrine and Epinephrine Synthesis page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000331036
0000311006
0000331036
0000311006
0000220017

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Daren W Brown et al.
Fungal genetics and biology : FG & B, 49(7), 521-532 (2012-06-02)
The genus Fusarium is of concern to agricultural production and food/feed safety because of its ability to cause crop disease and to produce mycotoxins. Understanding the genetic basis for production of mycotoxins and other secondary metabolites (SMs) has the potential
Brahim Bouizgarne et al.
Molecular plant-microbe interactions : MPMI, 19(5), 550-556 (2006-05-06)
Fusarium spp. are ubiquitous fungi found in soil worldwide as both pathogenic and nonpathogenic strains. The signals leading to disease or the absence of disease are poorly understood. We recently showed that fusaric acid (FA), a nonspecific toxin produced by
Angélica Gutiérrez-Sánchez et al.
Toxins, 13(4) (2021-05-01)
Fusarium kuroshium is the fungal symbiont associated with the ambrosia beetle Euwallacea kuroshio, a plague complex that attacks avocado, among other hosts, causing a disease named Fusarium dieback (FD). However, the contribution of F. kuroshium to the establishment of this
H Wang et al.
Life sciences, 65(9), 849-856 (1999-08-28)
This review article aims at summarizing research findings on the various pharmacological activities of fusaric acid (5-butylpicolinic acid), a mycotoxin produced by several Fusarium species which commonly infect cereal grains and other agricultural commodities. The actions of the toxin on
Geneviève Girard et al.
Microbiology (Reading, England), 157(Pt 2), 398-407 (2010-10-30)
The triggering of antibiotic production by various environmental stress molecules can be interpreted as bacteria's response to obtain increased fitness to putative danger, whereas the opposite situation - inhibition of antibiotic production - is more complicated to understand. Phenazines enable
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