(4E)-dehydrocitrals [(2E,4E)- and (2Z,4E)3,7-dimethyl-2,4,6-octatrienals] from acarid mite histiogaster sp. A096 (Acari: Acaridae)

Article abstract of DOI:10.1271/bbb.65.2749

A mixture of two monoterpenes was obtained as the opisthonotal gland secretion from unidentified Histiogaster sp. A096 (Acari: Acaridae), and their structures were elucidated to be (4E)-dehydrocitrals [(2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienals] by GC/MS, GC/FT-IR, UV and ¹H-NMR spectra. Both isomers of (4E)-dehydrocitral prepared by syntheses in 4 steps from 3-methyl-2-butenal with 34.2% yields (based on the ylide) were separated by column chromatography into the (2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal. Mass spectra together with GC retention times of the purified natural (4E)-dehydrocitrals were identical with those of synthetic (2E,4E)-3,7-dimethyl-2,4,6-octatrienal and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienal. The geometry at the 2-C position of both synthetic (4E)-dehydrocitrals was confirmed by NOESY analyses. This is the first identification of (4E)-dehydrocitrals from the animal kingdom.

Full text of DOI:10.1271/bbb.65.2749

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(4E)-Dehydrocitrals [(2E,4E)- and (2Z,4E)-3,7-
dimethyl-2,4,6-octatrienals] from Acarid Mite
Histiogaster sp. A096 (Acari: Acaridae)
Hiroyuki HIRAOKAa, Naoki MORIa, Ritsuo NISHIDAa & Yasumasa KUWAHARAa
a Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of
Agriculture, Kyoto University
Published online: 22 May 2014.
To cite this article: Hiroyuki HIRAOKA, Naoki MORI, Ritsuo NISHIDA & Yasumasa KUWAHARA (2001) (4E)-Dehydrocitrals
[(2E,4E)- and (2Z,4E)-3,7-dimethyl-2,4,6-octatrienals] from Acarid Mite Histiogaster sp. A096 (Acari: Acaridae),
Bioscience, Biotechnology, and Biochemistry, 65:12, 2749-2754, DOI: 10.1271/bbb.65.2749
To link to this article: http://dx.doi.org/10.1271/bbb.65.2749
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