Fusaric acid

Fusaric acid

Names
IUPAC name 5-Butylpyridine-2-carboxylic acid
Other names 5-Butylpicolinic acid Fusarinic acid Picolinic acid, 5-butyl-
Identifiers
CAS Number	536-69-6
ChemSpider	3324
EC Number	208-643-0
Jmol interactive 3D	Image
KEGG	C10146
MeSH	D005669
PubChem	3442
InChI 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) Key: DGMPVYSXXIOGJY-UHFFFAOYSA-N InChI=1/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13) Key: DGMPVYSXXIOGJY-UHFFFAOYAD
SMILES CCCCC1=CN=C(C=C1)C(=O)O
Properties
Chemical formula	C10H13NO2
Molar mass	179.22 g·mol^−1
Melting point	97 to 98 °C (207 to 208 °F; 370 to 371 K)
Related compounds
Related compounds	picolinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fusaric acid is a picolinic acid derivative.

Antibiotic (wilting agent) first isolated from the fungus Fusarium heterosporium.^[1]

It is typically isolated from various Fusarium species, and has been proposed for a various therapeutic applications. However, it is primarily used as a research tool.

Its mechanism of action is not well understood. It likely inhibits Dopamine beta-hydroxylase (the enzyme that converts dopamine to norepinephrine). It may also have other actions, such as the inhibition of cell proliferation and DNA synthesis.

It is used to make bupicomide.

References

1. Yabuta et al., J. Agric. Chem. Soc. Jpn. 10, 1059 (1934).