Synthesis and Characterization of Hexadecadienyl Compounds with a Conjugated Diene System, Sex Pheromone of the Persimmon Fruit Moth and Related Compounds(Organic Chemistry)
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概要
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Hexadecadien-1-ol and the derivatives (acetate and aldehyde) with a conjugated diene system have recently been identified from a pheromone gland extract of the persimmon fruit moth (Stathmopoda masinissa), a pest insect of persimmon fruits distributed in East Asia. The alcohol and acetate showed their base peaks at m/z 79 in a GC-MS analysis by electron impact ionization, but the aldehyde produced a unique base peak at m/z 84, suggesting a 4, 6-diene structure. To confirm this inference, four geometrical isomers of each 4, 6-hexadecadienyl compound were synthesized by two different routes in which one of two double bonds was furnished in a highly stereoselective manner. Separation of the two isomers synthesized together by each route was facilely accomplished by preparative HPLC. Their mass spectra coincided well with those of natural components, indicating that they were available for use as authentic standards for determining the configuration of the natural pheromone. Furthermore, other hexadecadienyl compounds, including the conjugated diene system between the 3- and 10-positions, were synthesized to accumulate the spectral data of pheromone candidates. 5, 7-Hexadecadienal interestingly showed the base peak at m/z 80 ; meanwhile, the base peaks of its alcohol and acetate were detected at m/z 79 like the corresponding 4, 6-dienes. The base peaks of all 6, 8-, 7, 9-, and 8, 10-dienes universally appeared at m/z 67 like 9, 11-, 10, 12-, and 13, 15-dienes, the spectra of which have already been published. Although 3, 5-hexadecadienal was not prepared, base peaks at m/z 67 and 79 were recorded for the alcohol and acetate, respectively.
- 社団法人日本農芸化学会の論文
- 2003-04-23
著者
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VANG Le
Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Tec
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Vang Le
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Naka Hideshi
National Institute For Agro-environmental Sciences (niaes):(present Office)laboratory Of Applied Ent
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Ando T
Department Of Applied Biological Science Faculty Of Agriculture Tokyo University Of Agriculture And
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Ando Tomoaki
Division Of Bioscience And Biotechnology Department Of Ecological Engineering Toyohashi University O
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ANDO Tetsu
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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TSUCHIDA Koji
Laboratory of Entomology, Faculty of Agriculture, Gifu University
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Naka Hideshi
Laboratory of Applied Entomology, Faculty of Agriculture, Tottori University
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YAMAZAWA Hiroyuki
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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NISHIDA Takanobu
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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YOSHIDA Ryuji
Graduate School of Bio-Applications and Systems Engineering (BASE), Tokyo University of Agriculture
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Yoshida Ryuji
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Ando T
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Ando Tetsu
Graduate School Of Bio-applications And Systems Engineering (base) Tokyo University Of Agriculture A
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Naka Hiromi
National Institute For Agro-environmental Sciences (niaes):(present Office)laboratory Of Applied Ent
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Tsuchida K
Division Of Radiological Protection And Biology National Institute Of Infectious Diseases
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Tsuchida Koji
Laboratory Of Ecological Entomology Faculty Of Applied Biological Sciences Gifu University
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Ando Tetsu
Graduate School Of Bio-applications And Systems Engineering Tokyo University Of Agriculture And Tech
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Yamazawa H
Fukui Prefectural Univ. Fukui Jpn
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Naka Hideshi
Laboratory Of Applied Entomology Faculty Of Agriculture Tottori University
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