methyl cis,cis-9,11-octadecadienoate | 822-10-6

• 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: methyl cis,cis-9,11-octadecadienoate
• 英文别名: cis,cis-Methyloctadecadienoat；(9Z,11Z)-9,11-Octadecadienoic acid methyl ester；methyl (9Z,11Z)-octadeca-9,11-dienoate
• CAS: 822-10-6
• 化学式: C₁₉H₃₄O₂
• 分子量: 294.478
• InChiKey: KVIWYYOMPLJRMC-XESWYYRISA-N

物化性质

• 熔点：
  54 °C
• 沸点：
  378.5±21.0 °C(Predicted)
• 密度：
  0.884±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：可溶；乙醇：可溶；己烷：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  -20°C，密封保存，置于干燥处。

制备方法与用途

9(Z),11(Z)-共轭亚油酸甲酯被用作通过气相色谱-质谱法量化共轭亚油酸甲酯的标准。

反应信息

• 作为产物：
  描述：

  methyl ricinoleate 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 methyl cis,cis-9,11-octadecadienoate
  参考文献：
  名称：

  由蓖麻油酸甲酯大规模合成顺式9-9，反式十八十八碳二烯酸甲酯

  摘要：

  AbstractThe conjugated linoleic acid methyl cis‐9,trans‐11‐octadecadienoate has been prepared on a large scale from methyl ricinoleate. Methyl ricinoleate was purified from castor esters by a partition method. It was converted to the mesylate, which was reacted with a base (1,8‐diazabicyclo[5,4,0]‐undec‐7‐ene) to give a product that contained 66% of the desired ester. Two urea crystallizations produced a product containing 83% methyl cis‐9,trans‐11‐octadecadienoate, the identity of which was confirmed by gas chromatography linked to mass spectrometry and by Fourier transform infrared spectroscopy. The remaining impurities were methyl cis‐9,cis‐11‐ and cis‐9‐,trans‐12‐octadecadienoate.

  DOI：

  10.1007/s11746-997-0018-z

文献信息

• Suppression of carcinoma using high purity conjugated fatty acid
  申请人：——

  公开号：US20010018453A1

  公开（公告）日：2001-08-30

  Treatment of carcinoma in a human is disclosed, including administering a therapeutically effective amount of a fatty acid having four carbons with two conjugated double bonds formed by reacting an ester of a fatty acid with a tosyl chloride or a mesyl chloride, the fatty acid having four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four. The tosylate or mesylate of the ester of the fatty acid having the chain of four carbon atoms such that carbon one bears one hydrogen and one hydroxyl group, carbon two bears two hydrogens, and a double bond is positioned between carbon three and four is reacted with diazabicyclo-undecene. The method includes administering to a human a highly purified fatty acid in accordance with the present invention.

  本发明公开了治疗人类癌症的方法，包括施用治疗有效量的脂肪酸，该脂肪酸具有四个碳原子，通过脂肪酸酯与甲苯磺酰氯或甲磺酰氯反应形成两个共轭双键，该脂肪酸具有四个碳原子，其中碳一含有一个氢和一个羟基，碳二含有两个氢，双键位于碳三和碳四之间。具有四个碳原子链的脂肪酸酯的对甲苯磺酸盐或甲磺酸盐与重氮双环十一烯反应，其中碳一含有一个氢和一个羟基，碳二含有两个氢，双键位于碳三和碳四之间。该方法包括向人类施用符合本发明的高纯度脂肪酸。
• Elucidation of Structural Isomers from the Homogeneous Rhodium-Catalyzed Isomerization of Vegetable Oils
  作者：Dejan D. Andjelkovic、Byungrok Min、Dong Ahn、Richard C. Larock

  DOI：10.1021/jf0612124

  日期：2006.12.1

  The structural isomers formed by the homogeneous rhodium-catalyzed isomerization of several vegetable oils have been elucidated. A detailed study of the isomerization of the model compound methyl linoleate has been performed to correlate the distribution of conjugated isomers, the reaction kinetics, and the mechanism of the reaction. It has been shown that [RhCl(C8H8)(2)](2) is a highly efficient and selective isomerization catalyst for the production of highly conjugated vegetable oils with a high conjugated linoleic acid (CLA) content, which is highly desirable in the food industry. The combined fraction of the two major CLA isomers [(9Z, 11E)-CLA and (10E, 12Z)-CLA] in the overall CLA mixture is in the range from 76.2% to 93.4%. The high efficiency and selectivity of this isomerization method along with the straightforward purification process render this approach highly promising for the preparation of conjugated oils and CLA. Proposed improvements in catalyst recovery and reusability will only make this method more appealing to the food, paint, coating, and polymer industries in the future.
• SEKI, KATSURA;KANEKO, RYOHEI;KOBAYASHI, KATSUO, YUKAGAKU, 38,(1989) N1, S. 949-954
  作者：SEKI, KATSURA、KANEKO, RYOHEI、KOBAYASHI, KATSUO

  DOI：——

  日期：——
• US5892074A
  申请人：——

  公开号：US5892074A

  公开（公告）日：1999-04-06
• US6160141A
  申请人：——

  公开号：US6160141A

  公开（公告）日：2000-12-12