Fusaric acid

Fusaric acid is a picolinic acid derivative and an antibiotic (wilting agent) first isolated from the fungus Fusarium heterosporium.[1]

Fusaric acid
Names
Preferred IUPAC name
5-Butylpyridine-2-carboxylic acid
Other names
5-Butylpicolinic acid
Fusarinic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.859
EC Number
  • 208-643-0
KEGG
MeSH D005669
UNII
  • 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) ☒N
    Key: DGMPVYSXXIOGJY-UHFFFAOYSA-N ☒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
  • CCCCC1=CN=C(C=C1)C(=O)O
Properties
C10H13NO2
Molar mass 179.219 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).
☒N verify (what is checkY☒N ?)
Infobox references

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. Fusaric acid and analogues also reported as quorum sensing inhibitors.[2]

It is used to make bupicomide.

References
  1. Yabuta et al., J. Agric. Chem. Soc. Jpn. 10, 1059 (1934).
  2. Tung et al., Eur. J. Med. Chem. https://dx.doi.org/10.1016/j.ejmech.2016.11.044.
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