(S)-(+)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid | 162110-37-4

• 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)-(+)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid
• 英文别名: 13-S-hydroxy-2E,3E,8E-tetradecatrienoic acid；(2E,4E,8E,13S)-13-hydroxytetradeca-2,4,8-trienoic acid
• CAS: 162110-37-4
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: UZOXUKLWMRPYCQ-HIGNJNIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-(+)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (2E,4E,8E)-(S)-13-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradeca-2,4,8-trienoic acid methyl ester
  参考文献：
  名称：

  A new hydroxytetradecatrienoic acid and its glyceryl esters from Valsa ambiens

  摘要：

  A new hydroxytetradecatrienoic acid and its two glyceryl esters were isolated from a culture filtrate of Valsa ambiens. 1-Hydroxytetradecatrienoyl-sn-glycerol and 3-hydroxytetradecatrienoyl-sn-glycerol, only differing in the configuration of carbon 2', were separated as their corresponding MTPA esters. The absolute stereochemistry of the asymmetric centre of the acid and the two asymmetric centres of the esters were determined by using advanced Mosher methodology. The glyceryl esters exhibited an inhibitory effect on the growth of lettuce roots and hypocotyls.

  DOI：

  10.1016/0031-9422(94)00654-c
• 作为产物：
  描述：

  ethyl (S)-(+)-5-tert-butyldimethylsilyloxyhexanoate 在 盐酸 、 氢氧化钾 、 草酰氯 、 二苯硫醚 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 苯 为溶剂， 反应 23.07h， 生成 (S)-(+)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid
  参考文献：
  名称：

  Synthesis of (S)-13-Hydroxy (2E,4E,8E)- and (2E,4E,8Z)-Tetradecatrienoic Acids

  摘要：

  以维蒂希反应为关键步骤，合成了(S)-13-羟基-(2E,4E,8E)-十四碳三烯酸(1)和(2E,4E,8Z)-十四碳三烯酸(2)。研究了不饱和羟基脂肪酸的结构与它们对莴苣生长的抑制作用之间的关系。

  DOI：

  10.1271/bbb.59.1032

文献信息

• Synthesis of (<i>S</i>)-13-Hydroxy (2<i>E</i>,4<i>E</i>,8<i>E</i>)- and (2<i>E</i>,4<i>E</i>,8<i>Z</i>)-Tetradecatrienoic Acids
  作者：Ying Jiao、Teruhiko Yoshihara、Akitami Ichihara

  DOI：10.1271/bbb.59.1032

  日期：1995.1

  The syntheses of (S)-13-hydroxy-(2E,4E,8E)-tetradecatrienoic acid (1) and (2E,4E,8Z)-tetradecatrienoic acid (2) were carried out by using the Wittig reaction as the key step. The asymmetric center at C-13 and the double bond between C-8 and C-9 for natural compound 1 were reconfirmed as being of (S) configuration and E, respectively.The relationship between the structure of the unsaturated hydroxy fatty acids and their inhibitory effect on the growth of lettuce was investigated.

  以维蒂希反应为关键步骤，合成了(S)-13-羟基-(2E,4E,8E)-十四碳三烯酸(1)和(2E,4E,8Z)-十四碳三烯酸(2)。研究了不饱和羟基脂肪酸的结构与它们对莴苣生长的抑制作用之间的关系。
• A new hydroxytetradecatrienoic acid and its glyceryl esters from Valsa ambiens
  作者：Ying Jiao、Teruhiko Yoshihara、Masanobu Akimoto、Akitami Ichihara

  DOI：10.1016/0031-9422(94)00654-c

  日期：1995.1

  A new hydroxytetradecatrienoic acid and its two glyceryl esters were isolated from a culture filtrate of Valsa ambiens. 1-Hydroxytetradecatrienoyl-sn-glycerol and 3-hydroxytetradecatrienoyl-sn-glycerol, only differing in the configuration of carbon 2', were separated as their corresponding MTPA esters. The absolute stereochemistry of the asymmetric centre of the acid and the two asymmetric centres of the esters were determined by using advanced Mosher methodology. The glyceryl esters exhibited an inhibitory effect on the growth of lettuce roots and hypocotyls.