Farinomalein

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Farinomalein
Farinomalein.svg
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
1175521-35-3
ChEBI CHEBI:718704
ChemSpider 24674945
Jmol 3D model Interactive image
PubChem 44254797
Properties
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 R43
S-phrases 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).[1]

Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae.[2] These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean.[2]

Synthesis[edit]

A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported.[3] 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.

References[edit]

  1. ^ Sastia P. Putri, Hiroshi Kinoshita, Fumio Ihara, Yasuhiro Igarashi and Takuya Nihira. Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus. J. Nat. Prod., 2009, 72 (8), pp 1544-1546 doi:10.1021/np9002806
  2. ^ a b Sastia Prama Putri, Hiroshi Kinoshita, Masayasu Kato and Takuya Nihira. Antimicrobial and antioomycete activities of the novel antibiotic farinomalein. Poster Presentation 2P-2124, Annual Conference, The Society for Bioscience and Bioengineering, Japan, 28 October 2010.
  3. ^ William H. Miles and Ming Yan. Synthesis of farinomalein. Tetrahedron Letters, 2010, 51 (13), pp 1710-1712 doi:10.1016/j.tetlet.2010.01.083

External links[edit]