(S)-17-hydroxylinolenic acid methyl ester | 307524-20-5

• 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: (S)-17-hydroxylinolenic acid methyl ester
• 英文别名: methyl (9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoate
• CAS: 307524-20-5
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: XDHWBDHWZKWCCN-KJLTXNDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-17-hydroxylinolenic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以90%的产率得到(9Z,12Z,15Z,17S)-17-hydroxyoctadeca-9,12,15-trienoic acid
  参考文献：
  名称：

  Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

  摘要：

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02640-0
• 作为产物：
  描述：

  8-溴辛酸 在 P₂-Ni 正丁基锂 、 三甲基氯硅烷 、 乙基溴化镁 、 氢气 、 三溴化磷 、 potassium iodide 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (S)-17-hydroxylinolenic acid methyl ester
  参考文献：
  名称：

  Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

  摘要：

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02640-0

文献信息

• Synthesis of the (17<i>R</i>)- and (17<i>S</i>)-Isomers of Volicitin, an Elicitor of Plant Volatiles Contained in the Oral Secretion of the Beet Armyworm
  作者：Seiji ITOH、Shigefumi KUWAHARA、Morifumi HASEGAWA、Osamu KODAMA

  DOI：10.1271/bbb.66.1591

  日期：2002.1

  Both the (17R)- and (17S)-isomers of volicitin, which is contained in the oral secretion of the beet armyworm and induces corn seedlings to emit a blend of volatile compounds to attract the natural enemy of the herbivore, were synthesized via the semi-hydrogenation of an intermediary diyne and (Z)-selective olefination as the key steps. They were both obtained as crystalline compounds.

  甜菜夜蛾口腔分泌物中含有伏立替汀，它能诱导玉米幼苗释放出一种混合挥发性化合物以吸引食草动物的天敌。通过中间体二炔的半氢化和（Z）选择性烯化作为关键步骤，合成了伏立替汀的(17R)-和(17S)-异构体。它们都是晶体化合物。
• Absolute Configuration of Volicitin from the Regurgitant of Lepidopteran Caterpillars and Biological Activity of Volicitin-Related Compounds
  作者：Yoshitsugu SAWADA、Naoko YOSHINAGA、Kenji FUJISAKI、Ritsuo NISHIDA、Yasumasa KUWAHARA、Naoki MORI

  DOI：10.1271/bbb.60133

  日期：2006.9.23

  Volicitin [N-(17-hydroxylinolenoyl)-L-glutamine] and N-linolenoyl-L-glutamine are known as insect-produced plant volatile elicitors. The absolute configuration of the hydroxylinolenoyl moiety of volicitin from three noctuid species, Helicoverpa armigera, Mythimna separata and Spodoptera litura, was determined to be all 17S in high enantiomeric excess. When treated with 30 pmol of (17S)- and (17R)-volicitin, corn seedlings were induced to release volatiles, there being no significant difference in the amount released between the two isomers. On the other hand, N-linolenoyl-L-glutamine was only about 30% as active as volicitin. Among several synthesized N-linolenoylamino acid conjugates, only the L-glutamine conjugate induced the emission of volatile organic compounds. These results show that the L-glutamine moiety of volicitin played a more critical role than the hydroxyl moiety, although both moieties affected the elicitor activity inducing the release of volatiles.

  已知伏立替汀[N-（17-羟基亚麻酸酰基）-L-谷氨酰胺]和 N-亚麻酸酰基-L-谷氨酰胺是昆虫产生的植物挥发性激发剂。经测定，来自三种夜蛾（Helicoverpa armigera、Mythimna separata 和 Spodoptera litura）的伏立特素羟基亚麻酰基的绝对构型均为 17S，对映体过量。用 30 pmol 的（17S）- 和（17R）-伏立奎宁处理玉米幼苗，诱导其释放挥发性物质，两种异构体释放的量没有显著差异。另一方面，N-亚麻酸酰-L-谷氨酰胺的活性只有伏立替汀的 30%。在几种合成的 N-亚麻酸酰氨基共轭物中，只有 L-谷氨酰胺共轭物能诱导挥发性有机化合物的释放。这些结果表明，伏立替汀的 L-谷氨酰胺分子比羟基分子起着更为关键的作用，尽管这两个分子都会影响诱导剂释放挥发性有机化合物的活性。
• Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin
  作者：Han-Xun Wei、Christopher L. Truitt、Paul W. Paré

  DOI：10.1016/s0040-4039(02)02640-0

  日期：2003.1

  An efficient synthesis of N-(17S-hydroxylinolenOyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated. (C) 2003 Elsevier Science Ltd. All rights reserved.