(4E)-Dehydrocitrals [(2E, 4E)- and (2Z, 4E)-3, 7-dimethyl-2, 4, 6-octatrienals] from Acarid Mite Histiogaster sp. A096 (Acari : Acaridae)(Organic Chemistry)

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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 (2Z, 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.
社団法人日本農芸化学会の論文
2001-12-23