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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:
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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
T Malovrh et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 48(10), 2907-2912 (2010-07-27)
Two groups of pregnant primiparous sows (day 89 ± 2 of gestation) were 54 days (± 1 day) fed either with an experimental diet (5.08 mg kg(-1) deoxynivalenol--DON, 0.09 mg kg(-1) zearalenone and 21.61 mg kg(-1) fusaric acid) or control
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