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
CAS Number	536-69-6 Y
3D model (JSmol)	Interactive image
ChemSpider	3324 N
ECHA InfoCard	100.007.859
EC Number	208-643-0
KEGG	C10146 N
MeSH	D005669
PubChem CID	3442
UNII	JWJ963070N Y
CompTox Dashboard (EPA)	DTXSID5023085
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) 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
SMILES CCCCC1=CN=C(C=C1)C(=O)O
Properties
Chemical formula	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 YN ?) 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.

External links

• Media related to Fusaric acid at Wikimedia Commons