(11Z,13E)-11,13-hexadecadien-1-ol | 111872-80-1

• 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: (11Z,13E)-11,13-hexadecadien-1-ol
• 英文别名: (11Z,13E)-hexadecadien-1-ol；11Z,13E-Hexadecadien-1-ol；(11Z,13E)-hexadeca-11,13-dien-1-ol
• CAS: 111872-80-1
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: GKFQVSXEEVMHMA-ICWBMWKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (11Z,13E)-11,13-hexadecadien-1-ol 在 吡啶 作用下， 以80%的产率得到(Z,E)-11,13-hexadecadienyl acetate
  参考文献：
  名称：

  Lo, Veng Meng; Shiao, Min-Jen, Synthetic Communications, 1986, vol. 16, # 13, p. 1647 - 1656

  摘要：

  DOI：
• 作为产物：
  描述：

  11-十二炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 bis(cyclohexanyl)borane 、 二乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 (11Z,13E)-11,13-hexadecadien-1-ol
  参考文献：
  名称：

  Arai, Koshi; Ando, Tetsu; Sakurai, Akira, Agricultural and Biological Chemistry, 1982, vol. 46, # 9, p. 2395 - 2398

  摘要：

  DOI：

文献信息

• (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。
• [EN] SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION<br/>[FR] SYNTHÈSE D'ALCOOLS OLÉFINIQUES PAR L'INTERMÉDIAIRE DE L'HYDROXYLATION TERMINALE ENZYMATIQUE
  申请人：PROVIVI INC

  公开号：WO2015176020A1

  公开（公告）日：2015-11-19

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了一种通过将不饱和或饱和碳氢基质与羟化酶酶接触来生产末端羟基化烯烃和炔烃的方法。用于执行本发明方法的示例末端羟化酶对碳氢基质的一个末端碳具有很强的选择性，包括但不限于非血红素双铁脂烷单氧酶、细胞色素P450（例如，CYP52和CYP153家族的细胞色素P450）以及长链烷烃羟化酶。在某些实施例中，末端羟基化的烯烃或炔烃进一步转化为末端烯醛。在某些实施例中，末端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素。在其他实施例中，末端羟基化的烯烃和炔烃是通过乙酰化或氧化醇基团来生产信息素的有用中间体。
• 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。
• SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
  申请人：Provivi, Inc.

  公开号：US20160108436A1

  公开（公告）日：2016-04-21

  In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.

  在某些方面，本发明提供了一种通过将不饱和或饱和的碳氢基质与一种羟化酶酶接触来生产端羟基化烯烃和炔烃的方法。用于执行本发明方法的示例端羟化酶对碳氢基质中的一个端碳具有强选择性，包括但不限于非血红素二铁烷烃单加氧酶、细胞色素P450（例如CYP52和CYP153家族的细胞色素P450）以及长链烷烃羟化酶。在某些实施例中，端羟基化的烯烃或炔烃进一步转化为端烯醛。在某些实施例中，端羟基化的烯烃和炔烃可用作改变昆虫行为的昆虫信息素。在其他实施例中，端羟基化的烯烃和炔烃是通过醋酸化或氧化醇基团来产生信息素的有用中间体。
• 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。