1-linoleoyl-2,3-dipalmitoylglycerol | 2535-35-5

• 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-linoleoyl-2,3-dipalmitoylglycerol
• 英文别名: 1,2-dihexadecanoyl-3-(9,12-octadecadienoyl)glycerol；1,2-dipalmitoyl-3-linoleoyl-rac-glycerol；dipalmitoyl-linoleoyl-rac-glycerol；α-Linoleoyl-β,α'-dipalmitin；glycerol-1,2-dipalmitate-3-linolate；Glycerin-1,2-dipalmitat-3-linolat；9Z,12Z-octadecadienoic acid, 2,3-bis[(1-oxohexadecyl)oxy]propyl ester；2,3-di(hexadecanoyloxy)propyl (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 2535-35-5
• 化学式: C₅₃H₉₈O₆
• 分子量: 831.358
• InChiKey: MTWYSKGJIDFSRC-DHSNEXAOSA-N

物化性质

• 熔点：
  36.5-38 °C
• 沸点：
  784.1±40.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：微溶；甲醇：微溶

计算性质

• 辛醇/水分配系数(LogP)：
  21.4
• 重原子数：
  59
• 可旋转键数：
  50
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-linoleoyl-2,3-dipalmitoylglycerol 以 甲醇 、 正己烷 、 异丙醇 为溶剂， 生成 2,3-dihexadecanoyl-1-cis-octadec-9,12-dienoyl-sn-glycerol 、 1,2-dipalmitoyl-3-linoleoylglycerol
  参考文献：
  名称：

  Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils

  摘要：

  Enantiomers of racemic triacylglycerol (TAG) mixtures were separated using two chiral HPLC columns with a sample recycling system and a UV detector. A closed system without sample derivatisation enabled separation and identification by using enantiopure reference compounds of eleven racemic TAGs with C12-C22 fatty acids with 0-2 double bonds. The prolonged separation time was compensated for by fewer pretreatment steps. Presence of one saturated and one unsaturated fatty acid in the asymmetric TAG favoured the separation. Enantiomeric resolution, at the same time with stronger retention of TAGs, increased with increasing fatty acid chain length in the sn-1(3) position. Triunsaturated TAGs containing oleic, linoleic or palmitoleic acids did not separate. The elution order of enantiomers was determined by chemoenzymatically synthesised enantiopure TAGs with a co-injection method. The method is applicable to many natural fats and oils of low unsaturation level assisting advanced investigation of lipid synthesis and metabolism. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2014.09.135
• 作为产物：
  描述：

  亚麻酰氯 在 吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-linoleoyl-2,3-dipalmitoylglycerol
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1016285801824

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。
• Practical Syntheses of Triacylglycerol Regioisomers Containing Long-chain Polyunsaturated Fatty Acids
  作者：Benjamin H. Fraser、Patrick Perlmutter、Chakra Wijesundera

  DOI：10.1007/s11746-006-1001-9

  日期：2007.1

  AbstractDocosahexaenoic acid (DHA, 22:6n‐3) is known to protect against a range of degenerative disease conditions and aid in the development of eye and brain function in infants. In dietary lipids DHA is found primarily in the triacylglycerol (TAG) form. However, the effects of the positional distribution of DHA in TAG on lipid functional properties such as bioactivity and oxidative stability are not clearly understood. Studies on this subject for the most part are limited by a lack of regioisomerically pure TAG model compounds containing DHA or similar long‐chain (LC)‐polyunsaturated fatty acids (PUFA). This paper reports on the development of a practical procedure, based on chemical and enzymatic reactions, for the syntheses of regioisomerically enriched, symmetrical and unsymmetrical TAG isomers containing two palmitic acid and one of linoleic acid, linolenic acid, or DHA. 1,3‐Selective acylation of glycerol with vinyl esters of fatty acids catalyzed by Candida antarctica lipase and direct coupling with fatty acids in the presence of the coupling agents 1‐(3‐dimethylaminopropyl)‐3‐ethylcarbodiimide hydrochloride and 4‐dimethylaminopyridine furnished 1,3‐dihexadecanoyl‐2‐docosahexaenoyl glycerol and its unsymmetrical isomer 1,2‐dihexadecanoyl‐3‐docosahexaenoyl glycerol in 99 and 60% yield, respectively. Critical to the success of the unsymmetrical TAG synthesis is the demonstration that PUFA‐containing glycerol acetonides can readily survive appropriately tailored acid‐catalyzed conditions. In this way, sufficient quantities of highly regioisomerically enriched PUFA‐containing unsymmetrical monoacylglycerols (MAG) and TAG have now become routinely accessible. The methods are amenable to scale‐up and could be adopted for regioenriched synthesis of a wide range of TAG.
• Synthesis and Physical Properties of Symmetrical and Non‐symmetrical Triacylglycerols Containing Two Palmitic Fatty Acids
  作者：R. O. Adlof、G. R. List

  DOI：10.1007/s11746-007-1173-y

  日期：2008.2

  AbstractA series of symmetrical (ABA) and non‐symmetrical (AAB) triacylglycerol (TAG) isomers containing “A,” palmitic (P; 16:0) acid, and “B,” either oleic (O; 9c‐18:1), elaidic (E; 9t‐18:1), linoleic (L; 9c,12c‐18:2) or linolenic (Ln; 9c,12c,15c‐18:3) fatty acids were synthesized by esterification of the thermodynamically more‐stable 1,3‐di‐ or 1(3)‐monoacylglycerols [1,3‐DAG or 1(3)‐MAG], respectively. 1,3‐dipalmitoylglycerol (1,3P‐DAG) was esterified with O, L or Ln acid to prepare the symmetrical TAG isomers POP, PLP and PLnP, while the O‐ E‐, L‐ and Ln‐1(3)MAG precursors, synthesized or obtained commercially, were esterified with P acid to prepare the non‐symmetrical TAG isomers OPP, EPP, LPP and LnPP, respectively. The drop point(s), solid fat content and melting point values of the synthesized TAG were determined. The 1,3‐dipalmitoylglycerol (1,3P‐DAG) and 1(3)P‐MAG precursors were prepared, in multi‐gram quantities, by partial glycerolysis (glycerol/p‐toluenesulfonic acid) of tripalmitin. After fractionation by silica gel chromatography, the 1(3)P‐MAG and 1,3P‐DAG isomers (ca. 80% of total MAG or DAG) were purified (>98%) by crystallization from acetone [silver ion‐HPLC was utilized to determine the structural purities of the DAG (or MAG) precursors, and the synthesized TAG]. Esterification of the appropriate, thermodynamically more‐stable MAG or DAG precursors was found to be a very versatile method for synthesis (in 80–90% yields) of multi‐gram (3–5 g) quantities of symmetrical and non‐symmetrical TAG isomers, in chemical and structural purities of >96 and 97–99%, respectively.
• Serebrennikova,G.A. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 2174 - 2176
  作者：Serebrennikova,G.A. et al.

  DOI：——

  日期：——
• ——
  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.