13-oxo-trideca-9Z,11E-dienoic acid methyl ester | 120728-18-9

• 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: 13-oxo-trideca-9Z,11E-dienoic acid methyl ester
• 英文别名: methyl (9Z,11E)-13-oxotrideca-9,11-dienoate
• CAS: 120728-18-9
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: KKONPTBIPYXILW-BABZSUFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-oxo-trideca-9Z,11E-dienoic acid methyl ester 在 porcine liver esterase 、 phosphate buffer 作用下， 反应 1.0h， 生成 (9Z,11E)-13-oxotrideca-9,11-dienoic acid
  参考文献：
  名称：

  硅藻中α，β，γ，δ-不饱和醛的合成及生物活性

  摘要：

  自从旋转硅藻Thalassiosira rotula分离出2,4-癸二烯醛和2,4,7-十二碳烯醛并表征其为细胞抗增殖代谢产物以来，α，β，γ，δ-不饱和醛类受到越来越多的关注。在该藻类以及其他硅藻物种中发现了与结构相关的α，β，γ，δ-不饱和醛。我们提供了该化合物类别的简短而通用的合成方法，以及对抑制海胆卵裂的潜力的结构活性研究。Pd 0-或Co II介导的5-碘-戊-2,4-二烯醛与有机锌的交叉偶联可从该通用前体快速灵活地合成许多醛。前体双键系统的立体化学在偶联过程中得以保留。生物测定法表明，与短链脂族同系物和共轭双系统的ω-氧代酸相比，侧链的极性对于抗增殖活性非常重要，其中2,4-癸二烯是最活泼的化合物。相反，双键几何形状对生物活性没有影响。α，β-不饱和2 E-癸烯也具有很高的活性，而在类似链长的饱和醛的情况下，活性降低。1-癸醇，2-癸酮和癸酸没有活性。

  DOI：

  10.1016/s0040-4020(03)00382-x
• 作为产物：
  描述：

  (9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid methyl ester 在 iron(II) sulfate 作用下， 生成 13-oxo-trideca-9Z,11E-dienoic acid methyl ester
  参考文献：
  名称：

  The rapid oxidative degradation of a phosphatidylcholine bearing an oxidatively modified acyl chain with a 2,4-dienal terminal

  摘要：

  Phosphatidyleholines (PCs) having an acyl chain with a 2,4-dienal terminal are expected to be important bioactive compounds formed during lipid peroxidation in vivo. However, they have not been isolated from biological tissues. Here we used electrospray mass spectroscopy to investigate whether a high autoxidative instability may contribute to the difficulty in detecting one such compound, 13-oxo-9,11-tridecadienoyl PC (OTDA-PC, 1). Although we found that pure, synthetic OTDA-PC was very stable, OTDA-PC formed during the decomposition of a PC bearing the 13-hydroperoxide of alpha-linolenic acid (PC-LNA-OOH, 2) was readily converted (i) anaerobically to its corresponding acid PC, 13-carboxy-9,11-tridecadienoyl PC, 3; (ii) aerobically to other bioactive aldehyde (or acid) PC species that have been detected in atherosclerotic tissues. We attribute the high oxidative instability of OTDA-PC to a high vulnerability of its carbonyl hydrogen [H-C(=O)R] to abstraction by lipid-derived radicals, and propose mechanisms for its conversion to the other oxidised PC species (vide supra). (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.04.004

文献信息

• First synthesis of phosphatidylcholine and cholesteryl derivatives bearing an unsaturated aldehyde residue
  作者：Arnold N. Onyango、Teruhiko Nitoda、Takao Kaneko、Mitsuyoshi Matsuo、Shuhei Nakajima、Naomichi Baba

  DOI：10.1039/b206231n

  日期：——

  The first synthesis of phosphatidylcholine and cholesteryl esters bearing a shortened acyl chain with a 2,4-dienal terminal is described.

  首次合成了具有2,4-二烯醛末端的短链酰基的磷脂酰胆碱和胆固醇酯。
• Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms
  作者：Sven Adolph、Serge A Poulet、Georg Pohnert

  DOI：10.1016/s0040-4020(03)00382-x

  日期：2003.4

  α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with

  自从旋转硅藻Thalassiosira rotula分离出2,4-癸二烯醛和2,4,7-十二碳烯醛并表征其为细胞抗增殖代谢产物以来，α，β，γ，δ-不饱和醛类受到越来越多的关注。在该藻类以及其他硅藻物种中发现了与结构相关的α，β，γ，δ-不饱和醛。我们提供了该化合物类别的简短而通用的合成方法，以及对抑制海胆卵裂的潜力的结构活性研究。Pd 0-或Co II介导的5-碘-戊-2,4-二烯醛与有机锌的交叉偶联可从该通用前体快速灵活地合成许多醛。前体双键系统的立体化学在偶联过程中得以保留。生物测定法表明，与短链脂族同系物和共轭双系统的ω-氧代酸相比，侧链的极性对于抗增殖活性非常重要，其中2,4-癸二烯是最活泼的化合物。相反，双键几何形状对生物活性没有影响。α，β-不饱和2 E-癸烯也具有很高的活性，而在类似链长的饱和醛的情况下，活性降低。1-癸醇，2-癸酮和癸酸没有活性。
• The rapid oxidative degradation of a phosphatidylcholine bearing an oxidatively modified acyl chain with a 2,4-dienal terminal
  作者：Arnold N Onyango、Shuhei Nakajima、Takao Kaneko、Mitsuyoshi Matsuo、Naomichi Baba

  DOI：10.1016/j.chemphyslip.2004.04.004

  日期：2004.8

  Phosphatidyleholines (PCs) having an acyl chain with a 2,4-dienal terminal are expected to be important bioactive compounds formed during lipid peroxidation in vivo. However, they have not been isolated from biological tissues. Here we used electrospray mass spectroscopy to investigate whether a high autoxidative instability may contribute to the difficulty in detecting one such compound, 13-oxo-9,11-tridecadienoyl PC (OTDA-PC, 1). Although we found that pure, synthetic OTDA-PC was very stable, OTDA-PC formed during the decomposition of a PC bearing the 13-hydroperoxide of alpha-linolenic acid (PC-LNA-OOH, 2) was readily converted (i) anaerobically to its corresponding acid PC, 13-carboxy-9,11-tridecadienoyl PC, 3; (ii) aerobically to other bioactive aldehyde (or acid) PC species that have been detected in atherosclerotic tissues. We attribute the high oxidative instability of OTDA-PC to a high vulnerability of its carbonyl hydrogen [H-C(=O)R] to abstraction by lipid-derived radicals, and propose mechanisms for its conversion to the other oxidised PC species (vide supra). (C) 2004 Elsevier Ireland Ltd. All rights reserved.