(ω5Z)-etherolenic acid methyl ester | 151675-37-5

• 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: (ω5Z)-etherolenic acid methyl ester
• 英文别名: methyl (9Z,11E)-12-[(1Z,3Z)-hexa-1,3-dienoxy]dodeca-9,11-dienoate
• CAS: 151675-37-5
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: OSVPXLNNMZEANH-XKJKOEOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (ω5Z)-etherolenic acid methyl ester 在 氢气 作用下， 生成 13-oxanonadecanoic 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：

  linolipin B 、 sodium methylate 以 甲醇 为溶剂， 生成 (ω5Z)-etherolenic acid methyl ester
  参考文献：
  名称：

  Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves

  摘要：

  Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(omega 5Z)-etherolenoyl-2-O-dinor-(omega 5Z)-etherolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z, 10Z)-hexadecadienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-0-(omega 5Z)-etherolenoyl-2-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, and 1-O-(omega 5Z)-etherolenoyl-2-O-palmitoyl-3-O-(alpha-galactopyranosyl-1-6-beta-D-galactopyranosyl)-sn-glycerol. The trivial names "linolipins E, F, G, H and I," respectively, have been ascribed to these novel complex oxylipins.

  DOI：

  10.1016/j.phytochem.2018.10.030

文献信息

• 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，
• Detection and identification of complex oxylipins in meadow buttercup (Ranunculus acris) leaves
  作者：Ivan R. Chechetkin、Alexander S. Blufard、Andrey Y. Yarin、Evgenia O. Fedina、Bulat I. Khairutdinov、Alexander N. Grechkin

  DOI：10.1016/j.phytochem.2018.10.030

  日期：2019.1

  Screening of linolipins, i.e. galactolipids containing esterified residues of divinyl ether oxylipins, in the leaves of several higher plants revealed the presence of these complex oxylipins in the meadow buttercup leaves. The rapid accumulation of linolipins occurred in the injured leaves of meadow buttercup, while intact leaves possessed no linolipins. These oxylipins were isolated from the injured leaves, separated and purified by HPLC. The structural analyses of linolipins by UV, mass-spectroscopy and NMR spectroscopy resulted in the identification of eight molecular species. Three of them were identical to linolipins B-D found earlier in the leaves of flax (Linum usitatissimum L.). Other molecular species were identified as 1-O-(omega 5Z)-etherolenoyl-2-O-dinor-(omega 5Z)-etherolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z,10Z,13Z)-hexadecatrienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-O-(omega 5Z)-etherolenoyl-2-O-(7Z, 10Z)-hexadecadienoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, 1-0-(omega 5Z)-etherolenoyl-2-O-alpha-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol, and 1-O-(omega 5Z)-etherolenoyl-2-O-palmitoyl-3-O-(alpha-galactopyranosyl-1-6-beta-D-galactopyranosyl)-sn-glycerol. The trivial names "linolipins E, F, G, H and I," respectively, have been ascribed to these novel complex oxylipins.