Farinomalein

Farinomalein

Names
IUPAC name 3-(2,5-dioxo-3-propan-2-ylpyrrol-1-yl)propanoic acid
Systematic IUPAC name 3-(3-isopropyl-2,5-dioxo-pyrrol-1-yl)propanoic acid
Other names 2,5-dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid
Identifiers
CAS Number	1175521-35-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:718704
ChemSpider	24674945
PubChem CID	44254797
InChI InChI=1/C10H13NO4/c1-6(2)7-5-8(12)11(10(7)15)4-3-9(13)14/h5-6H,3-4H2,1-2H3,(H,13,14)
SMILES CC(C)C1=CC(=O)N(C1=O)CCC(=O)O
Properties
Chemical formula	C10H13NO4
Molar mass	211.21 g/mol
Appearance	White powder
Density	1.281 (ACD/Labs)
Melting point	75 to 77 °C (167 to 171 °F; 348 to 350 K)
Boiling point	384.6 °C (724.3 °F; 657.8 K) Calculated (ACD/Labs)
Solubility	CH2Cl2, acetone, toluene, CH3OH
log P	1.34 (ACD/Labs)
Vapor pressure	0 mmHg (25 °C)
Hazards
R-phrases (outdated)	R43
S-phrases (outdated)	S22, S24, S37, S61.
Flash point	86.4 °C (187.5 °F; 359.5 K) (ACD/Labs)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Farinomalein is a natural maleimide with formula C₁₀H₁₃NO₄ - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).

Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae. These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean.

A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported. Firstly, 5-hydroxy-4-methyl-2-5(H)-furanone is oxidised to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane, followed by acetic acid reflux with beta-alanine. The white powdered product has a melting point of 75-77 °C.