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;
CompTox Dashboard (EPA)	DTXSID50658055 ;
	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
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

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

^ 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
^ ^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.
^ 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

[DiscoveryTeam-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

[2010JapaneseConfPaper-2] 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

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