(E)-2-(4′-Methyl-3′-pentenylidene)-4-butanolide, Named β-Acariolide: A New Monoterpene Lactone from the Mold Mite, Tyrophagus putrescentiae (Acarina: Acaridae)

Article abstract of DOI:10.1271/bbb.61.1906

Reinvestigation of the opisthonotal gland secretion of the mold mite, Tyrophagus putrescentiae, resulted in the isolation of a new monoterpene lactone, whose chemical structure was elucidated as (E)-2-(4′-methyl-3′-pentenylidene)-4-butanolide (3), to which we gave the trivial name β-acariolide in relation to β-acaridial {1, (E)-2-(4-methyl-3-pentenylidene)-butanedial}. The compound was synthesized by LiAlH₃ (OEt) reduction of 1 and subsequent oxidation involving simultaneous cyclization by using Ag₂CO₃ on Celite. Both the E- and Z-isomers of β-acariolide (3 and 4) were also prepared by the reaction of α-ethoxaly-γ-butyrolactone (6) and 4-methyl-3-pentenal under basic conditions. Their NMR spectra were compared with each other, and the geometry of the pentenylidene double bond of the isolated compound was concluded as being E.

Full text of DOI:10.1271/bbb.61.1906

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(E)-2-(4′-Methyl-3′-pentenylidene)-4-butanolide,
Named β-Acariolide: A New Monoterpene Lactone
from the Mold Mite, Tyrophagus putrescentiae
(Acarina: Acaridae)
Atsushi Morinoa, Yasumasa Kuwaharaab, Sigeru Matsuyamaa & Takahisa Suzukia
a Institute of Applied Biochemistry, University of Tsukuba, Tsukuba, Ibaraki 305, Japan
b Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University,
Sakyo-ku, Kyoto 606–01, Japan
Published online: 12 Jun 2014.
To cite this article: Atsushi Morino, Yasumasa Kuwahara, Sigeru Matsuyama & Takahisa Suzuki (1997) (E)-2-(4′-Methyl-3′-
pentenylidene)-4-butanolide, Named β-Acariolide: A New Monoterpene Lactone from the Mold Mite, Tyrophagus
putrescentiae (Acarina: Acaridae), Bioscience, Biotechnology, and Biochemistry, 61:11, 1906-1908, DOI: 10.1271/
bbb.61.1906
To link to this article: http://dx.doi.org/10.1271/bbb.61.1906
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