cis-12-oxo-10,15-phytodienoic acid methyl ester | 115510-01-5

• 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: cis-12-oxo-10,15-phytodienoic acid methyl ester
• 英文别名: Methyl-12-oxo-cis-10,15-phytodienoat；methyl 8-[(1S,5S)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoate
• CAS: 115510-01-5
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: AXDNONFPXLVMOY-IYZIGIFBSA-N

物化性质

• 沸点：
  404.8±24.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  cis-12-oxo-10,15-phytodienoic acid methyl ester 在 铂 氢气 作用下， 生成 (1S,2S)-3-oxo-2-pentylcyclopentane-1-octanoic acid methyl ester
  参考文献：
  名称：

  亚麻 (Linum usitatissimum L.) 叶中的脂氧合酶-二乙烯基醚合酶途径

  摘要：

  亚油酸与来自亚麻 (Linum usitatissimum L.) 叶的酶制剂一起孵育导致形成二乙烯基醚脂肪酸，即 (9Z,11E,1'Z)-12-(1'-己烯氧基)-9 ,11-dodecadienoic [(omega5Z)-etheroleic] 酸，以及少量的 13-hydroxy-9(Z),11(E)-octadecadienoic acid。亚油酸的 13-氢过氧化物提供了相同的产物，而 α-亚麻酸及其 13-氢过氧化物的孵育提供了二乙烯基醚 (9Z,11E,1'Z,3'Z)-12-(1', 3'-己二烯氧基)-9,11-十二碳二烯酸[(omega5Z)-etherolenic]作为主要产物。两种二乙烯基醚的鉴定均由它们的 UV、质量、(1)H NMR 和 COZY 光谱数据证实。除了这些结果证明的 13-脂肪氧化酶和二乙烯基醚合酶活性外，

  DOI：

  10.1016/j.phytochem.2008.04.012
• 作为产物：
  描述：

  Γ-十八碳三烯酸 在 氧气 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 cis-12-oxo-10,15-phytodienoic acid methyl ester
  参考文献：
  名称：

  Crombie, Leslie; Morgan, David O., Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 581 - 587

  摘要：

  DOI：

文献信息

• Synthesis of 12-oxophytodienoic acid (12-oxoPDA), metabolic parent of OPC-compounds and epi-jasmonic acid
  作者：Leslie Crombie、Kamlesh M. Mistry

  DOI：10.1039/c39880000537

  日期：——

  The first synthesis of (±)-12-oxophytodienoic acid, a compound widely distributed in plants, and the metabolic parent of OPC compounds including epi-jasmonic acid, is described; whilst structurally resembling prostaglandin PGA1, it belongs to the cis-series not found in mammals.

  （±）-12-oxophytodienoic酸的第一合成，化合物广泛分布于植物和OPC的代谢母体化合物包括外延-jasmonic酸，描述; 虽然在结构上类似于前列腺素PGA 1，但它属于在哺乳动物中未发现的顺式系列。
• Crombie, Leslie; Mistry, Kamlesh M., Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 1981 - 1991
  作者：Crombie, Leslie、Mistry, Kamlesh M.

  DOI：——

  日期：——
• Modular, Well-Behaved Reversible Polymers from DNA-Based Monomers
  作者：Elizabeth A. Fogleman、Wayne C. Yount、Jun Xu、Stephen L. Craig

  DOI：10.1002/1521-3773(20021104)41:21<4026::aid-anie4026>3.0.co;2-e

  日期：2002.11.4
• Oxylipins in the spikemoss Selaginella martensii: Detection of divinyl ethers, 12-oxophytodienoic acid and related cyclopentenones
  作者：Anna V. Ogorodnikova、Fakhima K. Mukhitova、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2015.08.003

  日期：2015.10

  Green tissues of spikemoss Selaginella martensii Spring possessed the complex oxylipins patterns. Major oxylipins were the products of linoleic and a-linolenic acids metabolism via the sequential action of 13-lipoxygenase and divinyl ether synthase (DES) or allene oxide synthase (AOS). AOS products were represented by 12-oxophytodienoic acid (12-oxo-PDA) isomers. Exceptionally, S. martensii possesses high level of 12-oxo-9(13),15-PDA, which is very uncommon in flowering plants. Separate divinyl ethers were purified after micro-preparative incubations of linoleic or alpha-linolenic acids with homogenate of S. martensii aerial parts. The NMR data allowed us to identify all geometric isomers of divinyl ethers. Linoleic acid was converted to divinyl ethers etheroleic acid, (11Z)-etheroleic acid and a minority of (omega 5Z)-etheroleic acid. With alpha-linolenate precursor, the specificity of divinyl ether biosynthesis was distinct. Etherolenic and (omega 5Z)-etherolenic acids were the prevailing products while (11Z)-etherolenic acid was a minor one. Divinyl ethers are detected first time in non-flowering land plant. These are the first observations of fatty acid metabolism through the lipoxygenase pathway in spikemosses (Lycopodiophyta). (C) 2015 Elsevier Ltd. All rights reserved.
• A lipoxygenase-divinyl ether synthase pathway in flax (Linum usitatissimum L.) leaves
  作者：Ivan R. Chechetkin、Alexander Blufard、Mats Hamberg、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2008.04.012

  日期：2008.7

  Incubation of linoleic acid with an enzyme preparation from leaves of flax (Linum usitatissimum L.) led to the formation of a divinyl ether fatty acid, i.e. (9Z,11E,1'Z)-12-(1'-hexenyloxy)-9,11-dodecadienoic [(omega5Z)-etheroleic] acid, as well as smaller amounts of 13-hydroxy-9(Z),11(E)-octadecadienoic acid. The 13-hydroperoxide of linoleic acid afforded the same set of products, whereas incubations

  亚油酸与来自亚麻 (Linum usitatissimum L.) 叶的酶制剂一起孵育导致形成二乙烯基醚脂肪酸，即 (9Z,11E,1'Z)-12-(1'-己烯氧基)-9 ,11-dodecadienoic [(omega5Z)-etheroleic] 酸，以及少量的 13-hydroxy-9(Z),11(E)-octadecadienoic acid。亚油酸的 13-氢过氧化物提供了相同的产物，而 α-亚麻酸及其 13-氢过氧化物的孵育提供了二乙烯基醚 (9Z,11E,1'Z,3'Z)-12-(1', 3'-己二烯氧基)-9,11-十二碳二烯酸[(omega5Z)-etherolenic]作为主要产物。两种二乙烯基醚的鉴定均由它们的 UV、质量、(1)H NMR 和 COZY 光谱数据证实。除了这些结果证明的 13-脂肪氧化酶和二乙烯基醚合酶活性外，