Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.
Structure, stereochemistry, and thermal isomerization of the male sex pheromone of the longhorn beetle Anaglyptus subfasciatus.
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长角甲虫 Anaglyptus subfasciatus 雄性性信息素的结构、立体化学和热异构化。
DOI：
10.1073/pnas.92.4.1038
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发表时间：
1995
影响因子：
11.1
通讯作者：
Meinwald,J
中科院分区：
文献类型：
--
作者：
Leal,WS;Shi,X;Nakamuta,K;Ono,M;Meinwald,J
用GC-MS和GC-Fourier变换红外光谱法鉴定了天牛Anaglyptus subfasciatus（鞘翅目：天牛科）雄性释放的性信息素成分为3-羟基-2-己酮和3-羟基-2-辛酮的摩尔比为7：1的混合物。这两种化合物在GC分析期间经历热异构化，得到相应的2-羟基-3-烷酮。天然产物与合成的对映体纯化合物的GC保留时间的比较表明，这两种化学信息素具有（R）-立体化学。这些绝对构型通过比较昆虫衍生样品和合成样品的（R）-甲氧基（三氟甲基）苯乙酸酯来证实。
Male-released sex pheromone constituents of the longhorn beetle Anaglyptus subfasciatus (Coleoptera: Cerambycidae) are identified by GC-MS and GC-Fourier transform infrared as a 7:1 molar mixture of 3-hydroxy-2-hexanone and 3-hydroxy-2-octanone. These two compounds undergo thermal isomerization during GC analyses to give the corresponding 2-hydroxy-3-alkanones. Comparison of GC retention times of the natural products with those of synthesized enantiomerically pure compounds revealed that both semiochemicals have (R)-stereochemistry. These absolute configurations were confirmed by comparisons of the (R)-methoxy(trifluoromethyl)phenylacetic acid esters of insect-derived and synthetic samples.