Farinomalein

Farinomalein
Identifiers
CAS number 1175521-35-3
PubChem 44254797
ChemSpider 24674945
ChEBI CHEBI:718704
Jmol-3D images Image 1
Properties
Molecular formula C10H13NO4
Molar mass 211.21
Appearance White powder
Density 1.281 (ACD/Labs)
Melting point

75-77 °C

Boiling point

384.6 °C, 658 K, 724 °F (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 186.4°C (ACD/Labs)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Farinomalein - 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

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

  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