(7Z,10Z)-hexadecadienoic acid methyl ester | 18829-90-8

• 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: (7Z,10Z)-hexadecadienoic acid methyl ester
• 英文别名: methyl (7Z,10Z)-hexadeca-7,10-dienoate
• CAS: 18829-90-8
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: UEDJSCQXZFTMLQ-NQLNTKRDSA-N

物化性质

• 沸点：
  346.1±21.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  19.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (7Z,10Z)-hexadecadienoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以64%的产率得到(7Z,10Z)-7,10-十六碳二烯酸
  参考文献：
  名称：

  Synthesis of the ω6 (5Z,8Z)-Tetradecadienoic and (7Z,10Z)-Hexadecadienoic Polyene Fatty Acids

  摘要：

  采用并优化了一种使用乙炔的方法来合成稀有天然ω6聚烯烃脂肪酸。关键的合成步骤是在等摩尔量的Cu(I)存在下，将丙炔衍生物与末端乙炔进行交叉耦合。

  DOI：

  10.1007/s10600-015-1195-x
• 作为产物：
  描述：

  2-辛炔酸 在 sodium tetrahydroborate 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 氢气 、 nickel(II) acetate tetrahydrate 、 potassium carbonate 、 乙二胺 、 sodium iodide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 17.5h， 生成 (7Z,10Z)-hexadecadienoic acid methyl ester
  参考文献：
  名称：

  Synthesis of the ω6 (5Z,8Z)-Tetradecadienoic and (7Z,10Z)-Hexadecadienoic Polyene Fatty Acids

  摘要：

  采用并优化了一种使用乙炔的方法来合成稀有天然ω6聚烯烃脂肪酸。关键的合成步骤是在等摩尔量的Cu(I)存在下，将丙炔衍生物与末端乙炔进行交叉耦合。

  DOI：

  10.1007/s10600-015-1195-x

文献信息

• Anti-tumour-promoting glyceroglycolipids from the green alga, Chlorella vulgaris
  作者：Takashi Morimoto、Akito Nagatsu、Nobutoshi Murakami、Jinsaku Sakakibara、Harukuni Tokuda、Hoyoku Nishino、Akio Iwashima

  DOI：10.1016/0031-9422(95)00458-j

  日期：1995.11

  Two new monogalactosyl diacylglycerols were isolated from the freshwater green alga, Chlorella vulgaris, as anti-tumour promoters, together with three monogalactosyl diacylglycerols and two digalactosyl diacylglycerols. The new monogalactosyl diacylglycerol containing (7Z,10Z)-hexadecadienoic acid showed a more potent inhibitory effect toward tumour promotion than the other glycerolipids isolated.
• 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.