3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-Acariolide and 4-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,β-Acariolide

• Published in: Bioscience, biotechnology, and biochemistry Vol. 66; no. 1; pp. 135 - 140
• Main Authors: TARUI, Hirokazu, MORI, Naoki, NISHIDA, Ritsuo, OKABE, Kimiko, KUWAHARA, Yasumasa
• Format: Journal Article
• Language: English
• Published: Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.01.2002
• Subjects: 3-(4-methyl-3-pentenyl)-2(5H)-furanone; monoterpene lactone; Schwiebea araujoae; α,α-acariolide; α,β-acariolide, 4-(4-methyl-3-pentenyl)-2(5H)-furanone
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.66.135

A new monoterpene lactone from the acarid mite, Schwiebea araujoae, was elucidated without its isolation by GC/FT-IR and GC/MS analyses to be 3-(4-methyl-3-pentenyl)-2(5H)-furanone (1) and tentatively named as α,α-acariolide. The structure of 1 was identified by its synthesis from α-bromo-γ-butyrolactone via 4 reaction steps. The synthesized compound gave the same GC/MS and GC/FT-IR spectra as those of the natural product. The other monoterpene lactone was likewise elucidated from the unidentified Rhizoglyphus mite to be 4-(4-methyl-3-pentenyl)-2(5H)-furanone (2) and named as α,β-acariolide; it was also identified by its synthesis in 5 reaction steps from the same butyrolactone as the starting material. GC/MS and GC/FT-IR spectra of the preparation were identical to those of the natural product.