Farinomalein
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| Preferred IUPAC name
3-[2,5-Dioxo-3-(propan-2-yl)-2,5-dihydro-1H-pyrrol-1-yl]propanoic acid | |
| Other names
2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C10H13NO4 | |
| Molar mass | 211.217 g·mol−1 |
| Appearance | White powder |
| Melting point | 75 to 77 °C (167 to 171 °F; 348 to 350 K) |
| Solubility | CH2Cl2, acetone, toluene, CH3OH |
| Vapor pressure | 0 mmHg (25 °C) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 | edit source]A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported.[3] Firstly, the furanone is oxidized 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
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- ^ 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.
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