Δ5-hexadecenol | 106463-48-3

• 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: Δ5-hexadecenol
• 英文别名: (Z)-5-Hexadecen-1-ol；Z-5-hexadecen-1-ol；5-hexadecenol, Z；(Z)-hexadec-5-en-1-ol
• CAS: 106463-48-3
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: KNVDHWATXBATDE-QXMHVHEDSA-N

物化性质

• 沸点：
  338.3±21.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)
• 保留指数：
  1867

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  Δ5-hexadecenol 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以95%的产率得到(Z)-1-bromohexadec-5-ene
  参考文献：
  名称：

  哺乳动物外分泌分泌物十五。雄性侏儒仓鼠（Phodopus sungorus sungorus）腹腺分泌成分。

  摘要：

  在一项旨在对雄性矮仓鼠（Phodopus sungorus sungorus）腹腺分泌成分进行化学表征的研究中，共有48种化合物，包括饱和醇，饱和和不饱和酮，饱和和不饱和直链羧酸，异和前异羧酸分泌物中鉴定出酸，3-苯基丙酸，羟基酯，2-哌啶酮和一些类固醇。无法确定γ-异二十二烯基-γ-丁内酯和γ-异二十二烯基-γ-丁内酯中双键的位置，以及在七个C16-C21饱和酮中的甲基支化位置。具有类固醇质谱的几种成分也仍未确定。雌性矮仓鼠

  DOI：

  10.1023/a:1010328331891
• 作为产物：
  描述：

  十六碳-5-炔-1-醇 在 sodium hydroxide 、 五氯化钽 、 锌 作用下， 生成 Δ5-hexadecenol
  参考文献：
  名称：

  Selective reduction of alkynes to (Z)-alkenes via niobium- or tantalum-alkyne complexes

  摘要：

  DOI：

  10.1021/jo00031a057

文献信息

• PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
  申请人：PROVIVI, INC.

  公开号：US20170137365A1

  公开（公告）日：2017-05-18

  In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R 1 is independently selected from H, C 1-18 alkyl, and C 2-18 alkenyl; R 2b is C 1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

  在一个方面，该发明提供了一种合成脂肪烯衍生物的方法。该方法包括：a）在存在一种烯烃催化剂的条件下，将符合式I的烯烃与符合式IIb的交换反应伙伴接触，以形成符合式IIIb的交换产物；并b）将交换产物转化为脂肪烯衍生物。每个R1独立地选择自H、C1-18烷基和C2-18烯基；R2为C1-8烷基；下标y为0至17之间的整数；下标z为0至17之间的整数。在某些实施方式中，交换催化剂为钨催化剂或钼催化剂。在各种实施方式中，脂肪烯衍生物为信息素。还描述了信息素组合物及其使用方法。
• [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。