ethyl 5Z,9Z,12Z-octadecatrienoate | 493015-74-0

• 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: ethyl 5Z,9Z,12Z-octadecatrienoate
• 英文别名: pinolenic acid ethyl ester；ethyl pinolenate；pinolenic acid(18:3)ethyl ester；ethyl (5Z,9Z,12Z)-octadeca-5,9,12-trienoate
• CAS: 493015-74-0
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: VNRWOSFYACMRHX-UCVSHGSNSA-N

物化性质

• 沸点：
  390.6±31.0 °C(Predicted)
• 密度：
  0.893±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL；乙醇：100mg/mL；乙醇:PBS (pH 7.2) (1:1): .5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-oxo-5-nonenoic acid ethyl ester 、 1,3-bis(triphenylphosphino)propane dibromide 、 正己醛 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 以12.0 mg的产率得到ethyl 5Z,9Z,12Z-octadecatrienoate
  参考文献：
  名称：

  5Z，9Z，12Z-十八碳三烯酸乙酯（松油酸乙酯）和12Z，15Z-十八碳二烯酸甲酯的合成

  摘要：

  AbstractPinolenic acid (5Z,9Z,12Z‐octadecatrienoic acid, 1a), one of the most abundant trienoic fatty acids in nature, is very difficult to obtain in quantity in a pure state from the highly complex mixture of unsaturated tall oil fatty acids. For this reason its chemistry has been little studied when compared to linolenic or linoleic acids. A simple synthesis of esters of 1a and of 12Z,15Z‐octadecadienoic acid 3 using the one pot double Wittig procedure is described here. The products of double Wittig reactions were purified by argentation chromatography, and their structural purity was established by 1H‐, 13C‐NMR and 2D‐NMR spectroscopies.

  DOI：

  10.1007/s11746-008-1226-x

文献信息

• Synthesis of Ethyl 5Z,9Z,12Z-octadecatrienoate (ethyl pinolenate) and Methyl 12Z,15Z-octadecadienoate
  作者：Seppo Kaltia、Jorma Matikainen、Maija Ala-Peijari、Tapio Hase

  DOI：10.1007/s11746-008-1226-x

  日期：2008.6

  AbstractPinolenic acid (5Z,9Z,12Z‐octadecatrienoic acid, 1a), one of the most abundant trienoic fatty acids in nature, is very difficult to obtain in quantity in a pure state from the highly complex mixture of unsaturated tall oil fatty acids. For this reason its chemistry has been little studied when compared to linolenic or linoleic acids. A simple synthesis of esters of 1a and of 12Z,15Z‐octadecadienoic acid 3 using the one pot double Wittig procedure is described here. The products of double Wittig reactions were purified by argentation chromatography, and their structural purity was established by 1H‐, 13C‐NMR and 2D‐NMR spectroscopies.