(Z,E)-11,13-hexadecadienyl acetate | 73784-69-7

• 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,E)-11,13-hexadecadienyl acetate
• 英文别名: (11Z,13E)-11,13-hexadecadienyl acetate；(11Z,13E)-11,13-hexadecadien-1-yl acetate；(11Z,13E)-11,13-Hexadecadienylacetat；(11Z,13E)-hexadecadien-1-yl acetate；11Z,13E-Hexadecadienolacetat；11Z,13E-Hexadecadienyl acetate；[(11Z,13E)-hexadeca-11,13-dienyl] acetate
• CAS: 73784-69-7
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: JDEZPVDDXSKIMP-DEQVHDEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (Z)-12-tert-Butoxy-1-iodo-dodec-1-ene 在 四(三苯基膦)钯 、 三氯化铁 作用下， 以 乙醚 为溶剂， 生成 (Z,E)-11,13-hexadecadienyl acetate
  参考文献：
  名称：

  The hydroalumination of ω-terbutoxy alkynes an easy access to ω-hydroxy alkenyl iodides application to the synthesis of dienic insect pheromones

  摘要：

  DOI：

  10.1016/s0040-4039(00)82315-1

文献信息

• Pheromone XXXIV. Synthese konjugiert-ungesättigter Lepidopterenpheromone und Analoga
  作者：Hans Jürgen Bestmann、Joachim Süß、Otto Vostrowsky

  DOI：10.1002/jlac.198119811205

  日期：1981.12.24

  Nach Art eines “Baukastensystems” werden konjugiert-ungesättigte Alkadienylacetate, Alkadienole und Alkadienale, wie sie als Sexualpheromone weiblicher Schmetterlinge bekannt sind, mit unterschiedlichen Positionen und Geometrien der Doppelbindungen synthetisiert.

  以“模块系统”的方式，合成了共轭-不饱和乙酸链二烯基乙酸酯，链二烯醇和链二烯醛，它们被称为雌性蝴蝶的性信息素，其双键的位置和几何结构不同。
• (11Z,13E)-Hexadecadien-1-yl Acetate: Sex Pheromone of the Grass Webworm Herpetogramma licarsisalis—Identification, Synthesis, and Field Bioassays
  作者：Andrew R. Gibb、D. Max Suckling、Ashraf M. El-Sayed、Björn Bohman、C. Rikard Unelius、Jennifer J. Dymock、Michelle L. Larsen、Bruce E. Willoughby

  DOI：10.1007/s10886-007-9259-4

  日期：2007.3.13

  The grass webworm Herpetogramma licarsisalis (Lepidoptera: Crambidae), which has recently established in pasture in Northland, New Zealand, is an important pest of many tropical and subtropical grasses. Two pheromone components, (Z)-11-hexadecen-1-yl acetate (Z11–16:Ac) and (11Z,13E)-hexadecadien-1-yl acetate (Z11,E13–16:Ac), were identified in pheromone gland extracts of female moths by gas chromatography (GC), GC-electroantennographic detection, and GC-mass spectrometry in conjunction with microchemical tests (dimethyldisulfide and 4-methyl-1,2,4-triazoline-3,5-dione derivatizations). Z11,E13–16:Ac and its geometric isomer (11E,13Z)-hexadecadien-1-yl acetate (E11,Z13–16:Ac) were synthesized via stereoselective Wittig reactions, and the identity of the diene present in the pheromone glands was confirmed to be Z11,E13–16:Ac. Field bioassays at Indooroopilly in Brisbane, Australia, established that Z11,E13–16:Ac was necessary and sufficient for attraction of male grass webworm moths and that the corresponding alcohol, (11Z,13E)-hexadecadien-1-ol (Z11,E13–16:OH), had a strong inhibitory effect on trap catches at the ratios tested. When mixed with Z11,E13–16:Ac in various ratios, Z11–16:Ac had no effect on the attractiveness of lures.

  草网虫Herpetogramma licarsisalis（鳞翅目：稻蝇科）最近在新西兰北地的牧场建立，是许多热带和亚热带草类的重要害虫。通过气相色谱（GC）、气相色谱-电极嗅觉检测（GC-EAD）和气相色谱-质谱（GC-MS）结合微化学测试（亚砜和4-甲基-1,2,4-三唑啉-3,5-二酮衍生化），在雌蛾的信息素腺提取物中确定了两种信息素成分，分别是（Z）-11-己十烯-1-基乙酸（Z11–16:Ac）和（11Z,13E）-己二烯-1-基乙酸（Z11,E13–16:Ac）。Z11,E13–16:Ac及其几何异构体（11E,13Z）-己二烯-1-基乙酸（E11,Z13–16:Ac）通过立体选择性Wittig反应合成，确认信息素腺中存在的二烯为Z11,E13–16:Ac。在澳大利亚布里斯班的Indooroopilly进行的田间生物测定表明，Z11,E13–16:Ac是吸引雄性草网虫蛾所必需和充分的，而相应的醇（11Z,13E）-己二烯-1-醇（Z11,E13–16:OH）在测试的比例下对捕捉具有强抑制作用。当与Z11,E13–16:Ac以不同比例混合时，Z11–16:Ac对诱捕器的吸引力没有影响。
• AGRICULTURAL PHEROMONE COMPOSITIONS COMPRISING POSITIONAL ISOMERS
  申请人：PROVIVI, INC.

  公开号：US20170135343A1

  公开（公告）日：2017-05-18

  The present disclosure provides pheromone compositions. In some aspects, the compositions taught herein comprise a pheromone chemically corresponding to the pheromone naturally produced by a given insect, along with at least one positional isomer of said pheromone. In various aspects, pheromone compositions of the present disclosure are able to modulate the response of the insect based on the ratio of natural pheromone to its positional isomer.

  本公开提供信息素组合物。在某些方面，本文所教授的组合物包括一种与某种昆虫自然产生的信息素在化学上相对应的信息素，以及至少一种该信息素的位置异构体。在各个方面，本公开的信息素组合物能够通过自然信息素与其位置异构体的比例来调节昆虫的反应。
• MULTI-SUBSTRATE METABOLISM FOR IMPROVING BIOMASS AND LIPID PRODUCTION
  申请人：Provivi, Inc.

  公开号：EP3564377A1

  公开（公告）日：2019-11-06

  The present application relates to methods to improve biomass or lipid production in a microorganism from one or more fatty acid and one or more simple carbon co-substrates. Produced lipids may include unsaturated C6-C24 fatty acids, alcohols, aldehydes, and acetates which may be useful as final products or precursors to insect pheromones, fragrances, flavors, and polymer intermediates. The application further relates to recombinant microorganisms modified for improved production of biomass or lipid, or improved lipid selectivity. Also provided are methods of producing one or more lipid using the recombinant microorganisms, as well as compositions comprising the recombinant microorganisms and/or optionally one or more of the product lipid.

  本申请涉及提高微生物中一种或多种脂肪酸和一种或多种单碳共底物的生物量或脂质产量的方法。生产的脂质可包括不饱和 C6-C24 脂肪酸、醇、醛和乙酸酯，它们可用作昆虫信息素、香料、香精和聚合物中间体的最终产品或前体。本申请还涉及为改进生物质或脂质的生产或改进脂质选择性而改良的重组微生物。还提供了使用重组微生物生产一种或多种脂质的方法，以及包含重组微生物和/或一种或多种产品脂质的组合物。
• SUSTAINED RELEASE PHEROMONE PREPARATION AND METHOD FOR CONTROLLING INSECT PEST USING THE SAME
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP3888460A1

  公开（公告）日：2021-10-06

  There is provided a sustained release pheromone preparation including a mixture containing a first unsaturated aliphatic acetate compound having one carbon-carbon double bond and a second unsaturated aliphatic acetate compound having two carbon-carbon double bonds in a mass ratio of 0.5:99.5 to 99.5:0.5, each compound having the same total number of carbon atoms; and a container containing the mixture therein and including, as a part or whole of the container, a membrane of a linear aliphatic polyester containing one or more selected from the following repeating unit (I); wherein the preparation targets at at least one type of insect pest whose sex pheromone substances contains both of the first and second compounds, or targets at at least one type of insect pest whose sex pheromone substance contains one of them and at least one type of insect pest sex pheromone substance or substances contains the other or both of them.

  本发明提供了一种缓释信息素制剂，包括一种混合物，其中含有具有一个碳碳双键的第一种不饱和脂肪族醋酸酯化合物和具有两个碳碳双键的第二种不饱和脂肪族醋酸酯化合物，其质量比为 0.5:99.5 至 99.5:0.5。5，每种化合物具有相同的碳原子总数；以及 一个容器，其中装有混合物，作为容器的一部分或整体，包括一层线性脂肪族聚酯膜，该膜含有选自以下重复单元 (I) 的一个或多个；其中制剂针对至少一种昆虫害虫，其性信息素物质含有第一和第二种化合物，或针对至少一种昆虫害虫，其性信息素物质含有其中一种，而至少一种昆虫害虫性信息素物质含有另一种或两种化合物。