1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol | 2190-19-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol
• 英文别名: 2-linoleoyl-1,3-dioleoylglycerol；glyceryl 1,3-dioleo 2-linoleate；1,2-dioleoyl-3-linolein；1,3-dioleoyl-2-linolein；1,3-diolein-2-linolein；OLO；9Z,12Z-octadecadienoic acid, 2-[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]-1-[[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]methyl]ethyl ester；[2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• CAS: 2190-19-4
• 化学式: C₅₇H₁₀₂O₆
• 分子量: 883.433
• InChiKey: UBFOEWXGSAZLKS-FVCHKXIASA-N

物化性质

• 沸点：
  818.0±65.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：微溶； DMF：10mg/mL；乙醇：10mg/mL；乙醇:PBS (pH 7.2) (1:1): 0.5 mg/mL
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  21.7
• 重原子数：
  63
• 可旋转键数：
  52
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  glycidyl oleate 在 六甲基磷酰三胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol
  参考文献：
  名称：

  Stereospecific synthesis of selected triglycerides: comments on acyl migration and analysis of configuration

  摘要：

  Symmetrical and stereospecifically defined triglycerides have been prepared from racemic and (R)- and (S)-glycidol, respectively. The synthetic sequence allows the incorporation of sensitive fatty acids such as linolenic acid. Justification for retention of configuration and absence of acyl migrations during the synthesis is provided by the H-1-NMR spectra of triglycerides that are replaced at the sn-1 and sn-3 positions with enantiomers of alpha-methoxytrifluoromethylphenylacetic acid (bis-MTPA esters). Partial hydrolysis of synthetic symmetrical triglycerides catalyzed by the lipase of Rhizopus oryzae was used to demonstrate the homogeneity of these preparations.

  DOI：

  10.1016/0009-3084(94)90101-5

文献信息

• Regioisomeric Characterization of Triacylglycerols Using Silver-Ion HPLC/MS and Randomization Synthesis of Standards
  作者：Miroslav Lísa、Hana Velínská、Michal Holčapek

  DOI：10.1021/ac900150j

  日期：2009.5.15

  Silver-ion normal-phase high-performance liquid chromatography (HPLC) provides a superior separation selectivity for lipids differing in the number and position of double bonds in fatty acid chains including the resolution of triacylglycerol (TG) regioisomers under optimized conditions. Our silver-ion HPLC method is based on the coupling of three columns in the total length of 75 cm and a new mobile phase gradient consisting of hexane−acetonitrile−2-propanol which provides better resolution and also reproducibility in comparison to previously used mobile phases. In our work, the chemical interesterification (randomization) of single-acid TG standards is used for the generation of regioisomeric series of TGs, because it provides a random distribution of fatty acids in TGs at well-defined concentration ratios. The baseline separation of regioisomeric TG pairs containing up to three double bonds and the partial separation of TG regioisomers with four to seven double bonds are reported for the first time. Our silver-ion high-performance liquid chromatography/mass spectrometry (HPLC/MS) method is applied for the regioisomeric characterization of complex samples of plant oils and animal fat, where the results clearly demonstrate different preference of sn-2 occupation in plants (mainly unsaturated fatty acids) versus animal fat (mainly saturated fatty acids).

  银离子正相高效液相色谱（HPLC）为脂质提供了优越的分离选择性，这些脂质在脂肪酸链中双键的数量和位置上存在差异，包括在优化条件下对甘油三酯（TG）位置异构体的分辨。我们的银离子HPLC方法是基于三根总长度为75厘米的柱子耦合以及一个新的由己烷、乙腈和丙酮醇组成的移动相梯度，这相比于之前使用的移动相提供了更好的分辨率和重复性。在我们的工作中，利用单酸TG标准的化学酯交换（随机化）来生成TG的位置异构体系列，因为这可以在明确定义的浓度比下提供脂肪酸在TG中的随机分布。首次报道了含有最多三个双键的位置异构体TG对的基线分离以及含有四到七个双键的TG位置异构体的部分分离。我们的银离子高效液相色谱/质谱（HPLC/MS）方法应用于植物油和动物脂肪的复杂样品的位置异构体特性鉴定，结果清楚地展示了在植物（主要是不饱和脂肪酸）和动物脂肪（主要是饱和脂肪酸）中sn-2占位偏好的不同。
• Certain metathesized natural oil triacylglycerol polyols for use in polyurethane applications and their related properties
  申请人：Trent University

  公开号：US10000442B2

  公开（公告）日：2018-06-19

  Metathesized triacylglycerol polyols derived from certain natural oils, including canola oil, and their related physical properties are disclosed. Such metathesized triacylglycerol polyols are also used as a component of polyurethane applications, including polyurethane foams.

  公开了从某些天然油（包括菜籽油）中提取的元化三酰甘油多元醇及其相关物理性质。此类偏聚三酰甘油多元醇还可用作聚氨酯应用（包括聚氨酯泡沫）的成分。
• Metathesized triacylglycerol polyols for use in polyurethane applications and their related properties
  申请人：Trent University

  公开号：US10000601B2

  公开（公告）日：2018-06-19

  Metathesized triacylglycerol polyols and their related physical and thermal properties are disclosed. Such metathesized triacylglycerol polyols are also used as a component of polyurethane applications, including polyurethane foams.

  公开了偏聚三酰甘油多元醇及其相关的物理和热性能。这种偏聚三酰甘油多元醇还可用作聚氨酯应用（包括聚氨酯泡沫）的成分。
• Metathesized triacylglycerol green polyols from palm oil for use in polyurethane applications and their related properties
  申请人：Trent University

  公开号：US10000724B2

  公开（公告）日：2018-06-19

  Metathesized triacylglycerol green polyols and their related physical and thermal properties are disclosed. Such metathesized triacylglycerol green polyols are also used as a component of polyurethane applications, including polyurethane foams.

  公开了偏聚三酰甘油绿色多元醇及其相关的物理和热性能。这种偏聚三酰甘油绿色多元醇还可用作聚氨酯应用（包括聚氨酯泡沫）的成分。
• ——
  作者：Junko Onodera、Shigeru Matsuyama、Takahisa Suzuki、Koichi Fujii

  DOI：10.1023/a:1016285801824

  日期：——

  Host-recognizing kairomones for the stinging behavior of the parasitic wasp, Anisopteromalus calandrae, were identified on host azuki bean weevil larvae, Callosobruchus chinensis (L.). The kairomones were extracted with acetone from Chinese green beans, from which emerged wasps and host weevils had been removed. The kairomones are a mixture of triacylglycerols and fatty acids, each of which is separately active, and with no observable synergistic effect between them. These compounds are known to be constituents of an oviposition-marking pheromone of host azuki bean weevils. However, they differ from the previously reported saturated hydrocarbons and diacylglycerols of the kairomone that another parasitic wasp, Dinarmus basalis, uses for the host recognition of C. chinensis. Thus, A. calandrae and D. basalis selectively utilize different constituents of the oviposition-marking pheromone of C. chinensis as host-recognizing kairomones.