2-(棕榈酰氧基)-1,3-丙烷二基(9E,9'E)二(-9-十八碳烯酸酯) | 1716-07-0

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 2-(棕榈酰氧基)-1,3-丙烷二基(9E,9'E)二(-9-十八碳烯酸酯)
• 中文别名: 1,3-二油酸-2-棕榈酸甘油三酯；1,3-二(十八烷-9-烯酸)-2-十六烷酸丙三醇酯
• 英文名称: 1,3-dioleoyl-2-palmitoylglycerol
• 英文别名: 1,3-olein-2-palmitin；[2-hexadecanoyloxy-3-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• CAS: 1716-07-0
• 化学式: C₅₅H₁₀₂O₆
• 分子量: 859.411
• InChiKey: PPTGNVIVNZLPPS-LBXGSASVSA-N

物化性质

• 熔点：
  19 °C
• 沸点：
  802.2±45.0 °C(Predicted)
• 密度：
  0.9046 g/cm3
• 溶解度：
  氯仿（微溶）、乙醇（微溶）、乙酸乙酯（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  22.2
• 重原子数：
  61
• 可旋转键数：
  52
• 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

安全信息

• WGK Germany：
  3
• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  2-(棕榈酰氧基)-1,3-丙烷二基(9E,9'E)二(-9-十八碳烯酸酯) 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Schuster, Journal de Pharmacie et de Chimie, 1932, vol. <8>16, p. 424,430,465

  摘要：

  DOI：
• 作为产物：
  描述：

  三棕榈酸甘油酯 在 rhizopus delemar lipase 、 lipozyme 、 乙醇 作用下， 以 正己烷 为溶剂， 反应 24.0h， 生成 2-(棕榈酰氧基)-1,3-丙烷二基(9E,9'E)二(-9-十八碳烯酸酯)
  参考文献：
  名称：

  脂肪酶催化合成甘油三酸酯反应条件的优化

  摘要：

  AbstractStructured triglycerides of the ABA‐type, containing one type of fatty acid (A) in the sn‐1 and sn‐3 positions and a second type of fatty acid (B) in the sn‐2 position of the glycerol, were synthesized using lipases. The highest yields and purities were achieved in a two‐step process, where a triglyceride of the B‐type was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn‐1,3‐regiospecific lipases yielding the corresponding 2‐monoglyceride (2‐MG). Using this strategy, e.g., 2‐monopalmitin (2‐MP) was obtained in up to 88% yield at >95% purity by crystallization. Esterification of 2‐MP with oleic acid resulted in the formation of 1,3‐oleyl‐2‐palmitoyl‐glycerol in up to 72% yield containing 94% palmitic acid in the sn‐2 position. The best lipases were from Rhizomucor miehei, Rhizopus delemar, and Rhizopus javanicus. Water activity, solvent, and carrier for lipase immobilization strongly influenced the yield and purity of the products in both steps. Furthermore, 2‐MG from fish oil were produced by alcoholysis in up to 84% yield at >95% purity.

  DOI：

  10.1007/s11746-998-0089-5

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。
• Atmospheric Pressure Covalent Adduct Chemical Ionization Tandem Mass Spectrometry for Double Bond Localization in Monoene- and Diene-Containing Triacylglycerols
  作者：Yichuan Xu、J. Thomas Brenna

  DOI：10.1021/ac062055a

  日期：2007.3.1

  We report a method to elucidate the structure of triacyl-glycerols (TAGs) containing monoene or diene fatty acyl groups by atmospheric pressure covalent adduct chemical ionization (APCACI) tandem mass spectrometry using acetonitrile as an adduct formation reagent. TAGs were synthesized with the structures ABB and BAB, where A is palmitate (C16:0) and B is an isomeric C18 monoene unsaturated at position

  我们报告了一种方法，通过使用乙腈作为加合物形成试剂的大气压共价加合物加成化学电离（APCACI）串联质谱法来阐明含有单烯或二烯脂肪酰基的三酰基甘油（TAG）的结构。TAGs的合成结构为ABB和BAB，其中A为棕榈酸酯（C16：0），B为9、11或13位不饱和的C18单烯异构体，或9、11、10和12位不饱和的二烯异构体。或9和12。除了在先前的CI研究中观察到的脂肪酸甲酯的m / z 54处的物种外，我们还发现m / z 42、81和95处的离子与包含双键的TAG进行共价反应在m / z 40、54、81和95单位处产生的离子比父TAG的离子大：[M + 40] +，[M + 54] +，[M + 81] +和[M + 95] +离子。当碰撞离解时，这些离子会碎裂以产生两个或三个诊断离子，这些离子将TAG中的双键定位。此外，由碰撞解离形成的离子[RCH = C = O + 40] +和[RCH
• Synthesis of triglycerides from 1,3-dibromopropan-2-ol
  作者：Asharam Bhati、Richard J. Hamilton、David A. Steven、Rajender Aneja、Frederick B. Padley

  DOI：10.1039/p29830001553

  日期：——

  1,3-Dibromopropan-2-ol (I) was converted into an acyl derivative (VI) by reaction with an appropriate acyl chloride in the presence of pyridine. The acyl derivative (VI) was subjected to nucleophilic substitution with 3 mol. equiv. tris(decyl)methylammonium carboxylate in refluxing hexane. This led to symmetrical diacid triglycerides in 90–94% yield. Substitution with an equimolar amount of the carboxylate

  通过在吡啶存在下与适当的酰氯反应，将1，3-二溴丙烷-2-醇（I）转化为酰基衍生物（VI）。对酰基衍生物（VI）进行3摩尔亲核取代。当量 在回流己烷中的羧酸三（癸基）甲基铵。这导致对称的二酸甘油三酯收率达到90-94％。用等摩尔量的羧酸取代，主要提供1,2-双酰氧基-3-溴丙烷（VII），可以轻松地将其分离并进一步取代，从而得到约不对称的二酸和三酸三甘油酯。产率96％。脂解显示合成的甘油三酸酯为约。纯度为99％。
• Functional associative coatings for nanoparticles
  申请人：Hainfeld James F.

  公开号：US20080089836A1

  公开（公告）日：2008-04-17

  Described herein are nanoparticles that are coated with a bilayer of molecules formed from surface binding molecules and amphiphatic molecules. The bilayer coating self assembles on the nanoparticles from readily available materials/molecules. The modular design of the bilayer coated nanoparticles provides a means for readily and efficiently optimizing the properties of the bilayer coated nanoparticle compositions. Also described herein are uses of such nanoparticles in medicine, laboratory techniques, industrial and commerical applications.

  本文描述了一种纳米颗粒，其表面涂覆有由表面结合分子和两亲分子形成的双层分子层。该双层涂层可以自组装在纳米颗粒上，使用易得的材料/分子。双层涂层纳米颗粒的模块化设计提供了一种方便和高效地优化其性质的方法。此外，本文还描述了这种纳米颗粒在医学、实验室技术、工业和商业应用中的用途。
• Synthesis of 1,3-olein-2-palmitin (OPO)
  申请人：SOCIETE DES PRODUITS NESTLE S.A.

  公开号：US11261401B2

  公开（公告）日：2022-03-01

  The present invention concerns a highly selective process for the preparation of an ingredient comprising 1,3-Olein-2-palmitin (OPO), a triglyceride present in human breast milk. The present invention also relates to 1,3-Olein-2-palmitin (OPO) ingredient obtainable by the process.

  本发明涉及一种制备成分的高度选择性过程，该成分包含1,3-油酸-2-棕榈酸甘油三酯（OPO），一种存在于人乳中的甘油三酯。本发明还涉及通过该过程获得的1,3-油酸-2-棕榈酸甘油三酯（OPO）成分。