E-11-hydroxy-octadeca-12-enoic acid | 308847-94-1

• 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: E-11-hydroxy-octadeca-12-enoic acid
• 英文别名: (E)-11-hydroxyoctadec-12-enoic acid
• CAS: 308847-94-1
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: ONAMALXVRDKFRJ-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 E-11-hydroxy-octadeca-12-enoic acid 以 乙醚 、 二氯甲烷 为溶剂， 以2.05 mg的产率得到(E)-methyl 11-hydroxyoctadec-12-enoate
  参考文献：
  名称：

  Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile

  摘要：

  从埃及地中海海岸采集的海洋绿藻Ulva fasciata Delile的二氯甲烷提取物中，分离出三种新的脂肪酸，分别是(E)-11-氧代十八碳十二烯酸（1a）、(E)-11-羟基十八碳十二烯酸（2a）和6-羟基辛-7-烯酸（3a），以及胆固醇。使用GC-MS分析提取物的非极性部分检测到另外十种化合物的存在，分别是二甲基亚砜、二甲基砜、苯乙酰胺、6,10,14-三甲基十五烷-2-酮、8-庚十七烯、十二烷、十三烷、4-氧代戊酸、十六烷酸和天然新的1,1'-双环己基。通过光谱分析，包括质谱（EI-MS，HR/ESIMS）、1D和2D NMR实验，以及合成转化为相应的甲酯1b-3b，确认了分离化合物1a-3a的结构。对海藻提取物及其组分进行了抗多种病原微生物和对溴盐虾的细胞毒性的比较研究。

  DOI：

  10.1515/znb-2009-1014
• 作为产物：
  描述：

  methyl 11-oxoundecanoate 在 二异丁基氢化铝 、 sodium hydroxide 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 5.0h， 生成 E-11-hydroxy-octadeca-12-enoic acid
  参考文献：
  名称：

  赤藻Tricleocarpa jejuensis的杀藻羟基化的C18不饱和脂肪酸：鉴定，合成和生物学活性。

  摘要：

  通过监测针对赤潮浮游植物沙门氏菌的拟南芥活性，生物测定指导的济州毛Tri甲醇提取物的分离导致分离出由四种异构体组成的活性部分。活性化合物鉴定为（E）-9-羟基十八碳烯-10 （1），（E）-10-羟基十八碳烯-8（2），（E）-11-羟基-12-12烯酸（3）和（E）-12-羟基十八烷基-10-烯酸（4NMR，IR和质谱数据）。结构通过与那些真实样品的NMR和MS数据的比较确认1 - 4由明确的合成而获得。合成的羟基酸1 - 4和相关化合物进行了评估针对杀藻活性C.蝇并且发现的所有1 - 4具有高的活性（> 80％的死亡率在第24小时）在20微克/ mL的浓度。使用11种相关化合物进行的结构-活性关系研究表明，羟基的存在对于活性很重要，双键可能被三键取代。

  DOI：

  10.1016/j.fitote.2020.104639

文献信息

• CHEMICAL AND BIOLOGICAL AGENTS FOR THE CONTROL OF MOLLUSCS
  申请人：Asolkar Ratnakar

  公开号：US20100266717A1

  公开（公告）日：2010-10-21

  Compositions and methods for controlling molluscs, members of the Gastropoda and Bivalvia classes which includes but is not limited to lactones, lactams, carbamates, amides, and/or carboxylic acid containing compounds as active ingredients and/or compounds derived from Pseudomonas and/or Erwinia . Also provided are methods and compositions for increasing the efficacy of chemical and biological control for invasive molluscs in open waters, power plants, and drinking water treatment facilities under coldwater conditions.

  用于控制软体动物的组合物和方法，该软体动物包括腹足纲和双壳纲的成员，其中包括但不限于内酯、内酰胺、氨基甲酸酯、酰胺和/或含有羧酸化合物作为活性成分和/或源自假单胞菌和/或厄尔文菌的化合物。还提供了用于在冷水条件下增加化学和生物控制对侵入性软体动物在开放水域、发电厂和饮用水处理设施中的功效的方法和组合物。
• Chemical and biological agents for the control of molluscs
  申请人：Marrone Bio Innovations, Inc.

  公开号：EP2601840A2

  公开（公告）日：2013-06-12

  Compositions and methods for controlling molluscs, members of the Gastropoda and Bivalvia classes which includes but is not limited to lactones, lactams, carbamates, amides, and/or carboxylic acid containing compounds as active ingredients and/ or compounds derived from Pseudomonas and/or Erwinia. Also provided are methods and compositions for increasing the efficacy of chemical and biological control for invasive molluscs in open waters, power plants, and drinking water treatment facilities under coldwater conditions.

  用于控制软体动物（腹足纲和双壳纲成员）的组合物和方法，包括但不限于内酯类、内酰胺类、氨基甲酸酯类、酰胺类和/或含羧酸的化合物作为活性成分和/或从假单胞菌和/或欧文氏菌衍生的化合物。此外，还提供了在冷水条件下提高对开放水域、发电厂和饮用水处理设施中入侵软体动物的化学和生物控制功效的方法和组合物。
• Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases
  作者：Ernst H. Oliw、Anneli Wennman、Inga Hoffmann、Ulrike Garscha、Mats Hamberg、Fredrik Jernerén

  DOI：10.1194/jlr.m018259

  日期：2011.11

  Seven Z-octadecenoic acids having the double bond located in positions 6Z to 13Z were photooxidized. The resulting hydroperoxy-E-octadecenoic acids [HpOME(E)] were resolved by chiral phase-HPLC-MS, and the absolute configurations of the enantiomers were determined by gas chromatographic analysis of diastereoisomeric derivatives. The MS/MS/MS spectra showed characteristic fragments, which were influenced by the distance between the hydroperoxide and carboxyl groups. These fatty acids were then investigated as substrates of cyclooxygenase-1 (COX-1), manganese lipoxygenase (MnLOX), and the (8R)-dioxygenase (8R-DOX) activities of two linoleate diol synthases (LDS) and 10R-DOX. COX-1 and MnLOX abstracted hydrogen at C-11 of (12Z)-18:1 and C-12 of (13Z)-18:1. (11Z)-18:1 was subject to hydrogen abstraction at C-10 by MnLOX and at both allylic positions by COX-1. Both allylic hydrogens of (8Z)-18:1 were also abstracted by 8R-DOX activities of LDS and 10R-DOX, but only the allylic hydrogens close to the carboxyl groups of (11Z)-18:1 and (12Z)-18:1. 8R-DOX also oxidized monoenoic C-14-C-20 fatty acids with double bonds at the (9Z) position, suggesting that the length of the omega end has little influence on positioning for oxygenation. We conclude that COX-1 and MnLOX can readily abstract allylic hydrogens of octadecenoic fatty acids from C-10 to C-12 and 8R-DOX from C-7 and C-12.-Oliw, E. H., A. Wennman, I. Hoffmann, U. Garscha, M. Hamberg, and F. Jerneren. Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases. J. Lipid Res. 2011. 52: 1995-2004.
• AGENTS FOR THE CONTROL OF LIMNOPERNA SP.
  申请人：Rackl Sarahann

  公开号：US20120121745A1

  公开（公告）日：2012-05-17

  Compositions and methods for controlling Limnoperna sp., particularly, golden mussels are provided using Pseudomonas sp. suspension or compounds and compositions derived from said suspension.
• CONTROL OF PHYTOPATHOGENIC MICROORGANISMS WITH PSEUDOMONAS SP. AND SUBSTANCES AND COMPOSITIONS DERIVED THEREFROM
  申请人：Marrone Bio Innovations, Inc.

  公开号：US20150030577A1

  公开（公告）日：2015-01-29

  Provided are compounds and compositions derived from Pseudomonas sp., particularly, Pseudomonas fluorescens or Pseudomonas protegens and more particularly strain having the identifying characteristics of Pseudomonas ATCC 55799 having antimicrobial properties and particularly, antibacterial properties.