9-oxo-cis-12-octadecenoic acid methyl ester | 34724-80-6

• 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: 9-oxo-cis-12-octadecenoic acid methyl ester
• 英文别名: Methyl-9-oxo-octadec-cis-12-enoat；methyl (Z)-9-oxooctadec-12-enoate
• CAS: 34724-80-6
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: QHDTWZCTFFLPPF-CLFYSBASSA-N

物化性质

• 沸点：
  408.8±28.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  22.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二甲基二硫 、 9-oxo-cis-12-octadecenoic acid methyl ester 在 吡啶 作用下， 以 正己烷 为溶剂， 生成 dimethyl disulfide adduct of 9-oxo-cis-12-octadecenoic acid FAME
  参考文献：
  名称：

  车前子种子脂质中含氧脂肪酸的鉴定与分布

  摘要：

  AbstractPlant oils rich in oxygenated fatty acids (FAs) are of interest as renewable raw materials for industry. Previous studies reported unusual oxygenated FAs in the seed lipids of Plantago major and P. ovata. To determine if oxygenated FAs are a common component of Plantago seed oils, seed fatty acyl quality and quantity were determined for 23 Plantago species. Fatty acyl content, as a percentage of dry weight, ranged from 4.9 % in P. sempervirens to 18.8 % in P. coronopus. Oxygenated FAs were a frequent, but not ubiquitous component of Plantago seed lipids, reaching a level of almost 15 % in the seeds of P. nivalis. The oxygenated FAs were identified as isoricinoleic acid (9‐hydroxy‐cis‐12‐octadecenoic acid, IR) and 9‐oxo‐cis‐12‐octadecenoic acid (OX). When present, most species contained both IR and OX. FAs containing oxo groups have not been reported as components of the seed oil of other plant species that synthesize IR or ricinoleic acid (12‐hydroxy‐cis‐9‐octadecenoic acid), suggesting unique aspects to the pathway of oxygenated FA biosynthesis in Plantago. Matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOF MS) demonstrated that IR and OX are components of triacylglycerol, and triacylglycerol estolides are a minor component of the seed oil of P. lanceolata with secondary acylation by oxygenated FAs.

  DOI：

  10.1007/s11746-014-2478-2
• 作为产物：
  描述：

  isoricinoleic acid methyl ester 在 chromium(VI) oxide 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以68 mg的产率得到9-oxo-cis-12-octadecenoic acid methyl ester
  参考文献：
  名称：

  车前子籽油中的一种新型氧代脂肪酸

  摘要：

  摘要 车前子籽油含有两种含氧脂肪酸，其中一种是已知的 9-羟基十八-顺式-12-烯酸。另一种是9-oxoact

  DOI：

  10.1016/s0031-9422(00)84595-1

文献信息

• A novel oxo fatty acid in Plantago ovata seed oil
  作者：Sajid Jamal、Ishtiaque Ahmad、Rajiv Agarwal、Mashood Ahmad、Sheikh Mohammad Osman

  DOI：10.1016/s0031-9422(00)84595-1

  日期：——

  Abstract Plantago ovata seed oil contains two oxygenated fatty acids one of which is the known 9-hydroxyoctadec- cis -12-enoic acid. The other is 9-oxoact

  摘要 车前子籽油含有两种含氧脂肪酸，其中一种是已知的 9-羟基十八-顺式-12-烯酸。另一种是9-oxoact
• Identification and Distribution of Oxygenated Fatty Acids in Plantago Seed Lipids
  作者：Mark A. Smith、Haixia Zhang、Randy W. Purves

  DOI：10.1007/s11746-014-2478-2

  日期：2014.8

  AbstractPlant oils rich in oxygenated fatty acids (FAs) are of interest as renewable raw materials for industry. Previous studies reported unusual oxygenated FAs in the seed lipids of Plantago major and P. ovata. To determine if oxygenated FAs are a common component of Plantago seed oils, seed fatty acyl quality and quantity were determined for 23 Plantago species. Fatty acyl content, as a percentage of dry weight, ranged from 4.9 % in P. sempervirens to 18.8 % in P. coronopus. Oxygenated FAs were a frequent, but not ubiquitous component of Plantago seed lipids, reaching a level of almost 15 % in the seeds of P. nivalis. The oxygenated FAs were identified as isoricinoleic acid (9‐hydroxy‐cis‐12‐octadecenoic acid, IR) and 9‐oxo‐cis‐12‐octadecenoic acid (OX). When present, most species contained both IR and OX. FAs containing oxo groups have not been reported as components of the seed oil of other plant species that synthesize IR or ricinoleic acid (12‐hydroxy‐cis‐9‐octadecenoic acid), suggesting unique aspects to the pathway of oxygenated FA biosynthesis in Plantago. Matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOF MS) demonstrated that IR and OX are components of triacylglycerol, and triacylglycerol estolides are a minor component of the seed oil of P. lanceolata with secondary acylation by oxygenated FAs.