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;
ChEMBL	ChEMBL1082049;
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	211.217 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)
Hazards
R-phrases (outdated)	R43
S-phrases (outdated)	S22-S24-S37-S61
	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, 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.

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References

Putri, Sastia P; Kinoshita, Hiroshi; Ihara, Fumio; Igarashi, Yasuhiro; Nihira, Takuya (2009). "Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus". Journal of Natural Products. 72 (8): 1544–6. doi:10.1021/np9002806. PMID 19670877.
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.
Miles, William H; Yan, Ming (2010). "Synthesis of farinomalein". Tetrahedron Letters. 51 (13): 1710. doi:10.1016/j.tetlet.2010.01.083.

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[1] Putri, Sastia P; Kinoshita, Hiroshi; Ihara, Fumio; Igarashi, Yasuhiro; Nihira, Takuya (2009). "Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus". Journal of Natural Products. 72 (8): 1544–6. doi:10.1021/np9002806. PMID 19670877.

[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] Miles, William H; Yan, Ming (2010). "Synthesis of farinomalein". Tetrahedron Letters. 51 (13): 1710. doi:10.1016/j.tetlet.2010.01.083.