fusaric acid
picolinic acid, 5-butyl-
 
Notes:
a picolinic acid derivative isolated from various fusarium species. it has been proposed for a variety of therapeutic applications but is primarily used as a research tool. its mechanisms of action are poorly understood. it probably inhibits dopamine beta-hydroxylase, the enzyme that converts dopamine to norepinephrine. it may also have other actions, including the inhibition of cell proliferation and dna synthesis.
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CAS Number: 536-69-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 208-643-0
FDA UNII: JWJ963070N
Nikkaji Web: J12.987I
Beilstein Number: 0125804
MDL: MFCD00006298
XlogP3-AA: 2.60 (est)
Molecular Weight: 179.21901000
Formula: C10 H13 N O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 97.00 °C. @ 760.00 mm Hg
Boiling Point: 329.20 °C. @ 760.00 mm Hg (est)
Flash Point: 307.00 °F. TCC ( 152.90 °C. ) (est)
logP (o/w): 1.960 (est)
Soluble in:
 water, 271.2 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Fusaric Acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Fusaric Acid from Gibberella fujikuroi
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-dog LD50  180 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

oral-dog LD50  200 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

intraperitoneal-mouse LD50  75 mg/kg
Journal of Pharmacobio-Dynamics. Vol. 6, Pg. 922, 1983.

intravenous-mouse LD50  100 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Antibiotics. Vol. 22, Pg. 228, 1969.

oral-mouse LD50  180 mg/kg
Journal of Pharmacobio-Dynamics. Vol. 6, Pg. 922, 1983.

intravenous-rabbit LD50  150 mg/kg
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

oral-rabbit LD50  310 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

intraperitoneal-rat LD50  250 mg/kg
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

intravenous-rat LD50  210 mg/kg
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

oral-rat LD50  480 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

Dermal Toxicity:
subcutaneous-mouse LD50 140 mg/kg
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

subcutaneous-rat LD50 300 mg/kg
Japanese Journal of Antibiotics. Vol. 29, Pg. 439, 1976.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for fusaric acid usage levels up to:
 not for fragrance use.
 
Recommendation for fusaric acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA GENetic TOXicology: Search
EPA Substance Registry Services (TSCA): 536-69-6
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 3442
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5-butylpyridine-2-carboxylic acid
Chemidplus: 0000536696
RTECS: US5625000 for cas# 536-69-6
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References:
 5-butylpyridine-2-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 3442
Pubchem (sid): 134977620
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10146
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2933.39.4700
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 trichoderma atroviride
Search  PMC Picture
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Synonyms:
5-butyl pyridine-3-carboxylic acid
5-butyl-2-pyridinecarboxylic acid
5-butylpicolinic acid
5-butylpyridine-2-carboxylic acid
5-N-butylpyridine-2-carboxylic acid
 fusarinic acid
 picolinic acid, 5-butyl-
 picolinic acid, 5-butyl- (8CI)
2-pyridinecarboxylic acid, 5-butyl-
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Articles:
PubMed: Native cell-death genes as candidates for developing wilt resistance in transgenic banana plants.
PubMed: Fusarium verticillioides SGE1 is required for full virulence and regulates expression of protein effector and secondary metabolite biosynthetic genes.
PubMed: Characterization of the fusaric acid gene cluster in Fusarium fujikuroi.
PubMed: The effects of different yeast extracts on secondary metabolite production in Fusarium.
PubMed: Determination of fusaric acid in maize using molecularly imprinted SPE clean-up.
PubMed: Contamination of bananas with beauvericin and fusaric acid produced by Fusarium oxysporum f. sp. cubense.
PubMed: Mycotoxins in corn and wheat silage in Israel.
PubMed: Masked mycotoxins: a review.
PubMed: Identification of gene clusters associated with fusaric acid, fusarin, and perithecial pigment production in Fusarium verticillioides.
PubMed: Single-kernel analysis of fumonisins and other fungal metabolites in maize from South African subsistence farmers.
PubMed: Ultrahigh-performance liquid chromatographic-tandem mass spectrometric multimycotoxin method for quantitating 26 mycotoxins in maize silage.
PubMed: Fusarium species (section Liseola) occurrence and natural incidence of beauvericin, fusaproliferin and fumonisins in maize hybrids harvested in Mexico.
PubMed: Nuclear magnetic resonance (NMR) studies on the biosynthesis of fusaric acid from Fusarium oxysporum f. sp. vasinfectum.
PubMed: Feed contaminated with Fusarium toxins alter lymphocyte proliferation and apoptosis in primiparous sows during the perinatal period.
PubMed: Identification, mycotoxin risk and pathogenicity of Fusarium species associated with fig endosepsis in Apulia, Italy.
PubMed: Effects of a deoxynivalenol-contaminated diet on the reproductive performance and immunoglobulin concentrations in pigs.
PubMed: [Study of specificity of fungistatic effect of trichothecene mycotoxins].
PubMed: Bikaverin and fusaric acid from Fusarium oxysporum show antioomycete activity against Phytophthora infestans.
PubMed: Effects of foodborne Fusarium mycotoxins with and without a polymeric glucomannan mycotoxin adsorbent on food intake and nutrient digestibility, body weight, and physical and clinicopathologic variables of mature dogs.
PubMed: Mycotoxins and the pet food industry: toxicological evidence and risk assessment.
PubMed: Mycotoxin producing Fusarium species associated with plant disease on potato, wheat, corn and animal diseases in northwest Iran.
PubMed: Growth-inhibiting effects of concentrations of fusaric acid on the growth of Bacillus mojavensis and other biocontrol Bacillus species.
PubMed: Effects of feeding blends of grains naturally contaminated with Fusarium mycotoxins on growth and immunological parameters of broiler chickens.
PubMed: Effects of feeding a blend of grains naturally contaminated with Fusarium mycotoxins on feed intake, serum chemistry, and hematology of horses, and the efficacy of a polymeric glucomannan mycotoxin adsorbent.
PubMed: Antioxidant nutrients and mycotoxins.
PubMed: Effects of feeding blends of grains naturally contaminated with Fusarium mycotoxins on production and metabolism in broilers.
PubMed: Intracerebroventricular injection of fusaric acid attenuates the anorexia by glucagon-like peptide-1 in the neonatal chick.
PubMed: Degradation and transformation of a potential natural herbicide in three soils.
PubMed: Fusaric acid and modification of the subchronic toxicity to rats of fumonisins in F. moniliforme culture material.
PubMed: Biological detoxification of fungal toxins and its use in plant breeding, feed and food production.
PubMed: Induction of food intake by a noradrenergic system using clonidine and fusaric acid in the neonatal chick.
PubMed: Production of fusaric acid by Fusarium species.
PubMed: Effects of mycotoxins on cytokine production and proliferation in EL-4 thymoma cells.
PubMed: Neuropharmacological studies on Fusarium toxins--II: Total toxin extract from F. oxysporum.
PubMed: Fusaric acid in Fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats.
PubMed: Decreased cell-mediated immunity and lack of skeletal problems in broiler chickens consuming diets amended with fusaric acid.
PubMed: Taxonomy and biology of Fusarium moniliforme.
PubMed: Biological and chemical characterization of metabolites of Fusarium moniliforme isolates.
PubMed: Dopamine-beta-hydroxylase inhibitors, feeding and locomotor activity: reinstatement of feeding following central norepinephrine.
PubMed: Mouse bioassay for Fusarium metabolites: rejection or acceptance when dissolved in drinking water.
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