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FUSARIC ACID

Product Name
FUSARIC ACID
CAS No.
536-69-6
Chemical Name
FUSARIC ACID
Synonyms
Fusaric;NSC 135043;FURASIC ACID;FUSARIC ACID;fusarinicacid;Fusarinic acid;FUSARIC ACID 99%;Fusaric acid,99%;Butylpicolinic acid;5-BUTYLPICOLINIC ACID
CBNumber
CB4689029
Molecular Formula
C10H13NO2
Formula Weight
179.22
MOL File
536-69-6.mol
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FUSARIC ACID Property

Melting point:
96-100 °C
Boiling point:
311.75°C (rough estimate)
Density 
1.1248 (rough estimate)
refractive index 
1.5710 (estimate)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
ethanol: 50 mg/mL, clear, faintly yellow
form 
Crystalline Powder
pka
1.11±0.50(Predicted)
color 
Off-white to faint yellow
Merck 
14,4314
BRN 
125804
LogP
1.960 (est)
CAS DataBase Reference
536-69-6(CAS DataBase Reference)
EPA Substance Registry System
2-Pyridinecarboxylic acid, 5-butyl- (536-69-6)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
24/25
RIDADR 
2811
WGK Germany 
3
RTECS 
US5625000
10
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29333999
Hazardous Substances Data
536-69-6(Hazardous Substances Data)
Toxicity
LD50 orally in mice: 230 mg/kg (Ishii)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
F6513
Product name
Fusaric acid
Purity
from
Packaging
1g
Price
$309
Updated
2024/03/01
Sigma-Aldrich
Product number
55952
Product name
Fusaric acid
Purity
for HPLC derivatization, ≥99.0% (HPLC)
Packaging
1g
Price
$395
Updated
2024/03/01
TCI Chemical
Product number
F0227
Product name
5-Butylpyridine-2-carboxylic Acid
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$423
Updated
2024/03/01
Cayman Chemical
Product number
17876
Product name
Fusaric Acid
Purity
≥98%
Packaging
50mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
17876
Product name
Fusaric Acid
Purity
≥98%
Packaging
100mg
Price
$48
Updated
2024/03/01
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FUSARIC ACID Chemical Properties,Usage,Production

Chemical Properties

off-white to faint yellowish crystalline powder

Uses

A medical research tool.

Uses

Fusaric acid may be used as a derivatizing reagent for the quantification of hydroxysteroids and dehydroepiandrosterone (DHEA)?and sulfated DHEA in biological samples using liquid chromatography electrospray-ionization-tandem mass spectrometry (LC/ESI-MS/MS) technique.

Definition

A mycotoxin and picolinic acid, that is an antibiotic and wilting agent that causes yellowing of infected plants.

Synthesis Reference(s)

The Journal of Organic Chemistry, 66, p. 605, 2001 DOI: 10.1021/jo0013554

General Description

Fusaric acid is a novel proton-affinitive derivatizing agent, having an ionization moiety and a hydrophobic moiety. It is commonly used for the derivatization of alcohols and phenols, by liquid chromatography coupled with electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS).

Hazard

Very toxic.

Biological Activity

fusaric acid is a mycotoxin produced by several species of fusarium [1]. mycotoxins are biologically active secondary fungal metabolites found as contaminants of food- and feedstuff. mycotoxin is capable of causing disease and death in both humans and animals.fusaric acid is a potent inhibitor of dopamine β-hydroxylase. fusaric acid uncompetitively inhibited the activity of dopamine β-hydroxylase with an ic50 of 30 μm in an. fusaric acid lowered endogenous levels of norepinephrine and epinephrine in brain, spleen, heart, and adrenal glands. fusaric acid inhibited dopamine β-hydroxylase activity in adrenal medulla in vivo [2]. fusaric acid altered brain and pineal neurotransmitters. in the brain and pineal gland of rats, intraperitoneally (100 mg/kg) administration of fusaric acid increased the level of 5ht, 5-hydroxyindoleacetic acid (5hiaa), tyrosine, and dopamine [3].exposure to acute doses of fusaric acid caused vomiting and neurochemical changes in swine. fusaric acid might act synergistically with trichothecene mycotoxins to cause vomiting and feed refusal in pigs consuming trichothecene-contaminated feedstuffs [4].

Safety Profile

A poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Dissolve it in CHCl3, dry (Na2SO4), filter, evaporate and recrystallise the residue from 50 parts of pet ether (b 40-60o), CHCl3/pet ether or EtOAc, then sublime it in vacuo. The amide crystallises from MeOH with m 128.2-129.0o. The copper salt forms bluish violet crystals from H2O and has m 258-259o. [Hardegger & Nikles Helv Chim Acta 39 505 1956, Schreiber & Adam Chem Ber 93 1848 1960, NMR and MS: Tschesche & Führer Chem Ber 111 3500 1978, Beilstein 22 III/IV 764, 22/2 V 384.]

References

[1] hidaka h, nagatsu t, takeya k, et al. fusaric acid, a hypotensive agent produced by fungi[j]. the journal of antibiotics, 1969, 22(5): 228-230.
[2] toshiharu n, hiroyoshi h, hiroshi k, et al. inhibition of dopamine β-hydroxylase by fusaric acid (5-butylpicolinic acid) in vitro and in vivo[j]. biochemical pharmacology, 1970, 19(1): 35-44.
[3] porter j k, bacon c w, wray e m, et al. fusaric acid in fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats[j]. natural toxins, 1995, 3(2): 91-100.
[4] smith t k, macdonald e j. effect of fusaric acid on brain regional neurochemistry and vomiting behavior in swine[j]. journal of animal science, 1991, 69(5): 2044-2049.

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FUSARIC ACID Suppliers

TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28398
Advantage
80

536-69-6, FUSARIC ACIDRelated Search:


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  • Fusaric Acid 5-Butylpicolinic Acid
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