(±)-cis-12-oxo-10-phytoenoic acid

• 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: (±)-cis-12-oxo-10-phytoenoic acid
• 英文别名: (±)-cis-12-OPEA；cis-12-oxo-10-phytoenoic acid；(1S,2S)-4-oxo-5-pentyl-2-cyclopentene-1-octanoic acid；8-[(1S,5S)-4-oxo-5-pentylcyclopent-2-en-1-yl]octanoic acid
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: DYAIBFMALFTKBR-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-cis-12-oxo-10-phytoenoic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以97%的产率得到8-((1S,2S)-3-Oxo-2-pentyl-cyclopentyl)-octanoic acid
  参考文献：
  名称：

  Biological activity and biosynthesis of pentacyclic oxylipins: The linoleic acid pathway

  摘要：

  The relevance of the postulated pathway from linoleic acid to dihydrojasmonic acid is analysed. Pentacyclic oxylipins having pentenyl or pentyl side chains were tested for their secondary metabolite inducing activity in seven different plant cell culture species which all responded well to 12-oxo-phytodienoic acid and jasmonic acid. The response towards the dihydro-derivatives 15,16-dihydro-12-oxo-phytodienoic acid and 9,10-dihydrojasmonic acid ranged from strong activity in Eschscholzia californica to no activity in Lycopersicon esculentum. 15,16-Dihydro-12-oxo-phytodienoic acid can be formed from linoleic acid (18:2) by a linseed acetone powder enzyme preparation. Application experiments with linoleic (18:2) and linolenic acid (18:3) showed that the bottleneck of the 18:2 pathway is most likely the cyclization of the intermediate allene oxide when compared to the ease by which 15,16-dihydro-12-oxo-phytodienoic acid is converted to dihydrojasmonic acid in plant systems. The metabolism of potential precursors of jasmonic and dihydrojasmonic acid was extensively studied in various cell cultures. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(97)00572-4
• 作为产物：
  描述：

  13(S)--过氧羟基-9,11-十八碳二烯酸 在 N,O-双三甲硅基乙酰胺 、 K-Pi buffer 、 linseed Me₂CO 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以0.7 mg的产率得到(±)-cis-12-oxo-10-phytoenoic acid
  参考文献：
  名称：

  Biological activity and biosynthesis of pentacyclic oxylipins: The linoleic acid pathway

  摘要：

  The relevance of the postulated pathway from linoleic acid to dihydrojasmonic acid is analysed. Pentacyclic oxylipins having pentenyl or pentyl side chains were tested for their secondary metabolite inducing activity in seven different plant cell culture species which all responded well to 12-oxo-phytodienoic acid and jasmonic acid. The response towards the dihydro-derivatives 15,16-dihydro-12-oxo-phytodienoic acid and 9,10-dihydrojasmonic acid ranged from strong activity in Eschscholzia californica to no activity in Lycopersicon esculentum. 15,16-Dihydro-12-oxo-phytodienoic acid can be formed from linoleic acid (18:2) by a linseed acetone powder enzyme preparation. Application experiments with linoleic (18:2) and linolenic acid (18:3) showed that the bottleneck of the 18:2 pathway is most likely the cyclization of the intermediate allene oxide when compared to the ease by which 15,16-dihydro-12-oxo-phytodienoic acid is converted to dihydrojasmonic acid in plant systems. The metabolism of potential precursors of jasmonic and dihydrojasmonic acid was extensively studied in various cell cultures. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(97)00572-4

文献信息

• Biosynthesis of Jasmonates from Linoleic Acid by the Fungus <i>Fusarium oxysporum</i> . Evidence for a Novel Allene Oxide Cyclase
  作者：Ernst H. Oliw、Mats Hamberg

  DOI：10.1002/lipd.12180

  日期：2019.9

  13(S)‐12‐oxophytoenoic acid, the 15,16‐dihydro analog of 12‐OPDA, was formed upon incubation of unlabeled or d5‐18:2n‐6. Appearance of the α‐ketol, 12‐oxo‐13‐hydroxy‐9‐octadecenoic acid following incubation of unlabeled or [13C18]‐labeled 13(S)‐hydroperoxy‐9(Z),11(E)‐octadecadienoic acid confirmed the involvement of AOS and the biosynthesis of the allene oxide 12,13(S)‐epoxy‐9,11‐octadecadienoic acid. The lack

  尖孢镰刀菌f。sp 。郁金香（FOT）会向生长培养基分泌（+）-7-异茉莉单酰基-（S）-异亮氨酸（（+）-JA-Ile）以及约10倍的9,10-二氢-（+）-7 -异-ja-ILE。植物和真菌从18：3n-3通过12-氧代苯二酸（12-OPDA ）形成（+）-JA-Ile ，其依次由13 S-脂氧合酶，氧化烯合酶（AOS）和氧化烯环化酶（ AOC）。植物AOC不接受亚油酸（18：2n-6）衍生的烯丙基氧化物，二氢茉莉酮酸酯在植物中不常见。这就提出了一个问题：18：2n-6是否在镰刀菌中用作9,10-dihydro-JA-Ile的前体，或者后者是否由在（+）-JA-Ile或其前体之一的n-3双键上起作用的假定还原酶活性引起。pentadeuterated（d孵育5）18：3N-3导致d的形成菌丝体5 - （+） - JA-ILE而d 5 -9,10-二氢JA-ILE是不可检测的。相反，在[17
• Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots
  作者：Anna V. Ogorodnikova、Larisa R. Latypova、Fahima K. Mukhitova、Lucia S. Mukhtarova、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2008.09.011

  日期：2008.11

  Incubations of linoleic acid with cell-free preparations from Lily-of-the-Valley (Convallaria majalis L, Ruscaceae) roots revealed the presence of 13-lipoxygenase and divinyl ether synthase (DES) activities. Exogenous linoleic acid was metabolized predominantly into (9Z,11E,1'E)-12-(1'-hexenyloxy)-9,11-dodecadienoic (etheroleic) acid. Its identification was confirmed by the data of ultraviolet spectroscopy, mass spectra, H-1 NMR, COSY, catalytic hydrogenation. The isomeric divinyl ether (8E,1'E,3'Z)-1 2-(1',3'-nonadienyloxy)-8-nonenoic (colneleic) acid was detected as a minor product. Incubations with linoleic acid hydroperoxides revealed that 13-hydroperoxide was a preferential substrate, while the 9-hydroperoxide was utilized with lesser efficiency. (C) 2008 Elsevier Ltd. All rights reserved.
• Biological activity and biosynthesis of pentacyclic oxylipins: The linoleic acid pathway
  作者：Heidrun Gundlach、Meinhart H. Zenk

  DOI：10.1016/s0031-9422(97)00572-4

  日期：1998.2

  The relevance of the postulated pathway from linoleic acid to dihydrojasmonic acid is analysed. Pentacyclic oxylipins having pentenyl or pentyl side chains were tested for their secondary metabolite inducing activity in seven different plant cell culture species which all responded well to 12-oxo-phytodienoic acid and jasmonic acid. The response towards the dihydro-derivatives 15,16-dihydro-12-oxo-phytodienoic acid and 9,10-dihydrojasmonic acid ranged from strong activity in Eschscholzia californica to no activity in Lycopersicon esculentum. 15,16-Dihydro-12-oxo-phytodienoic acid can be formed from linoleic acid (18:2) by a linseed acetone powder enzyme preparation. Application experiments with linoleic (18:2) and linolenic acid (18:3) showed that the bottleneck of the 18:2 pathway is most likely the cyclization of the intermediate allene oxide when compared to the ease by which 15,16-dihydro-12-oxo-phytodienoic acid is converted to dihydrojasmonic acid in plant systems. The metabolism of potential precursors of jasmonic and dihydrojasmonic acid was extensively studied in various cell cultures. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.