(Z)-3-Hexenyl (R)-2-hydroxy-3-methylbutyrate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-Hexenyl (R)-2-hydroxy-3-methylbutyrate
• 英文别名: 3Z-Hexenyl 2R-hydroxy-3-methylbutyrate；[(Z)-hex-3-enyl] (2R)-2-hydroxy-3-methylbutanoate
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: DGPCWWZIQGEZER-WWQCOOJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  D-缬氨酸 在 硫酸 、 对甲苯磺酸 、 sodium nitrite 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (Z)-3-Hexenyl (R)-2-hydroxy-3-methylbutyrate
  参考文献：
  名称：

  Identification, synthesis, and bioactivity of a male-produced aggregation pheromone in assassin bug,Pristhesancus Plagipennis (Hemiptera: Reduviidae)

  摘要：

  Pristhesancus plagipennis, a large Australian assassin bug, possesses three pairs of dorsal abdominal glands (DAGs). In the male, the anterior and posterior glands are hypertrophied and secrete an attractant pheromone. Gas chromatography-mass spectrometry (GC-MS) analyses of male DAG extracts and airborne volatiles emitted from calling males showed the pheromone signature to be dominated by a novel component. Subsequent chemical manipulations, GC-MS, and chiral-column analyses established its identity as (Z)-3-hexenyl (R)-2-hydroxy-3-methylbutyrate. Minor components included 3-methylbutanol, 2-phenylethanol, (Z)-3-hexenol, decanal, (E)-2-hexenoic acid, and three minor hexenyl esters. Bioactivity studies using laboratory olfactometers and outdoor flight cages demonstrated attraction by female P. plagipennis to calling males, heptane extracts of male posterior DAGs and a synthetic formulation of the (Z)R enantiomer of the major ester, alone or in combination with other components of male anterior and posterior DAGs. Males were also attracted to the major ester. The racemate and S enantiomer of the ester were not attractive. Contamination of the (Z)R enantiomer with 30-60% of the E isomer also made the compound nonattractive. This is the first report of an aggregation pheromone in the Reduviidae. The prospects for pheromonal manipulation of P. plagipennis populations to enhance the value of this predator in horticultural ecosystems, are discussed.

  DOI：

  10.1007/bf02033726

文献信息

• Identification, synthesis, and bioactivity of a male-produced aggregation pheromone in assassin bug,Pristhesancus Plagipennis (Hemiptera: Reduviidae)
  作者：David G. James、Christopher J. Moore、Jeffrey R. Aldrich

  DOI：10.1007/bf02033726

  日期：1994.12

  Pristhesancus plagipennis, a large Australian assassin bug, possesses three pairs of dorsal abdominal glands (DAGs). In the male, the anterior and posterior glands are hypertrophied and secrete an attractant pheromone. Gas chromatography-mass spectrometry (GC-MS) analyses of male DAG extracts and airborne volatiles emitted from calling males showed the pheromone signature to be dominated by a novel component. Subsequent chemical manipulations, GC-MS, and chiral-column analyses established its identity as (Z)-3-hexenyl (R)-2-hydroxy-3-methylbutyrate. Minor components included 3-methylbutanol, 2-phenylethanol, (Z)-3-hexenol, decanal, (E)-2-hexenoic acid, and three minor hexenyl esters. Bioactivity studies using laboratory olfactometers and outdoor flight cages demonstrated attraction by female P. plagipennis to calling males, heptane extracts of male posterior DAGs and a synthetic formulation of the (Z)R enantiomer of the major ester, alone or in combination with other components of male anterior and posterior DAGs. Males were also attracted to the major ester. The racemate and S enantiomer of the ester were not attractive. Contamination of the (Z)R enantiomer with 30-60% of the E isomer also made the compound nonattractive. This is the first report of an aggregation pheromone in the Reduviidae. The prospects for pheromonal manipulation of P. plagipennis populations to enhance the value of this predator in horticultural ecosystems, are discussed.