1,2-dipalmitoyl-3-oleoyl-rac-glycerol | 1867-91-0

• 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: 1,2-dipalmitoyl-3-oleoyl-rac-glycerol
• 英文别名: 1,2-dipalmitoyl-3-oleoylglycerol；1-Oleodipalmitin；2,3-Dipalmito-1-olein；2,3-di(hexadecanoyloxy)propyl (Z)-octadec-9-enoate
• CAS: 1867-91-0
• 化学式: C₅₃H₁₀₀O₆
• 分子量: 833.373
• InChiKey: YHMDGPZOSGBQRH-QPLCGJKRSA-N

物化性质

• 熔点：
  33-35°C
• 沸点：
  782.6±30.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（轻微）、二氯甲烷（轻微）、己烷（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  22.1
• 重原子数：
  59
• 可旋转键数：
  51
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

制备方法与用途

1,2-二棕榈酰-3-油酰甘油是一种主要的含磷三酰甘油，可以在棕榈油、棕榈硬脂、可可脂和猪油中找到。

反应信息

• 作为反应物：
  描述：

  1,2-dipalmitoyl-3-oleoyl-rac-glycerol 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 1,2-dipalmitoyl-3-(9,10-epoxystearoyl)-glycerol
  参考文献：
  名称：

  Structural analysis of hydroperoxy- and epoxy-triacylglycerols by liquid chromatography mass spectrometry

  摘要：

  Oxidation of triacylglycerols (TAGs) containing oleic acid leads to the formation of several products. This study characterizes hydroperoxy- and epoxy-TAGs including their regio-isomers. For this purpose, epoxy- and hydroperoxy-TAGs, formed by oxidation of 1,2-dipalmitoyl-3-oleoyl-glycerol (PPO) and 1,3-dipalmitoyl-2-oleoyl-glycerol (POP) under air and 1802, were analysed by reverse phase liquid chromatography-electrospray ionisation-mass spectrometry (LC-ESI-MS) using a triple quadrupole mass analyser, in positive ion mode. Post-column infusion of ammonium formiate was used to obtain intense molecular ion adducts. Pure 1,2-dipalmitoyl-3-epoxystearoyl-glycerol (PPEs) and 1,3-dipalmitoyl-2-epoxystearoyl-glycerol (PEsP), synthesized by epoxidation of the corresponding monounsaturated TAGs, were used to confirm MS/MS identification. The use of 1802 oxidation experiments permitted unambiguous identification of MS/MS fragmentation pathways of both hydroperoxide and epoxy-TAGs. Fragmentation. of hydroperoxy-TAGs are very distinct from their epoxy-TAGs homologues and consist of simultaneous losses of hydrogen peroxide (34 a.m.u.) and water (18 a.m.u.). (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.03.008
• 作为产物：
  描述：

  (2,2-二甲基-1,3-二氧戊环-4-基)甲基(9E)-9-十八碳烯酸酯 在 吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-dipalmitoyl-3-oleoyl-rac-glycerol
  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。
• FRACTIONATED PALM OIL AND PROCESS FOR PRODUCING THE SAME
  申请人：ASAHI DENKA KOGYO KABUSHIKI KAISHA

  公开号：EP1120455A1

  公开（公告）日：2001-08-01

  A fractionated palm oil is characterized by including linoleyldipalmitin (P2L) of 2~8 % by weight and oleoyldipalmitin (P2O) of 70% by weight or more. The fractionated palm oil of the present invention has a sharp melting property, and provides chocolates with an excellent heat resistance, snap property, sharp melting property in the palate, without blending with other fats and oil, and inhibits of the increase in viscosity during the tempering process.

  分馏棕榈油的特点是亚油酰二棕榈酸（P2L）的重量百分比为 2%至 8%，油酰二棕榈酸（P2O）的重量百分比为 70%或以上。本发明的分馏棕榈油具有极佳的熔融性，可为巧克力提供极佳的耐热性、咬合力和极佳的熔融性，且不会与其他油脂混合，并可抑制回火过程中粘度的增加。
• FAT-AND-OIL COMPOSITIONS FOR INHIBITING THE MIGRATION OF WATER IN FOOD AND FOODS MADE BY USING THE SAME
  申请人：Fuji Oil Company, Ltd.

  公开号：EP1787521A1

  公开（公告）日：2007-05-23

  The present invention aims at providing fat-and-oil compositions which can effectively inhibit the migration of water even when a low-water-content component is in contact with a high-water-content component and foods made by using the same. Namely, a fat-and-oil composition for inhibiting the migration of water in food wherein the fat-and-oil component contains a 1,2-saturated-3-unsaturated glyceride (SSU) in an amount of 15wt% or above but preferably below 50 wt% and a 1,3-saturated-2-unsaturated glyceride (SUS) in an amount of less than 50 wt%; fat-and-oil compositions as described above which further contain at least one member selected from among mono-diglycerides, sorbitan tristearate, and acetylated sucrose fatty acid esters, or a solid matter other than fats and oils; and foods containing, between low-water-content regions and high-water-content regions, the fat-and-oil compositions for inhibiting the migration of water.

  本发明旨在提供即使在低含水量成分与高含水量成分接触时也能有效抑制水分迁移的油脂组合物以及使用该组合物制成的食品。即，一种用于抑制食品中水分迁移的油脂组合物，其中的油脂成分含有1,2-饱和-3-不饱和甘油酯（SSU），含量为15wt%或以上，但最好低于50wt%，以及1,3-饱和-2-不饱和甘油酯（SUS），含量低于50wt%；如上所述的油脂组合物，其中还含有至少一种选自单甘油酯、山梨糖醇三硬脂酸酯和乙酰化蔗糖脂肪酸酯的成分，或油脂以外的固体物质；以及在低含水量区和高含水量区之间含有上述油脂组合物的食品，用于抑制水的迁移。
• PROCESS FOR PRODUCTION OF HARD BUTTER SUITABLE FOR CHOCOLATE PRODUCT
  申请人：The Nisshin Oillio, Ltd.

  公开号：EP2042607A1

  公开（公告）日：2009-04-01

  There is provided a process for preparing a fat and oil having a 1,3-disaturated long-chain fatty acid 2-monounsaturated long-chain fatty acid triglyceride (SUS)/1,2-disaturated long-chain fatty acid 3-monounsaturated long-chain fatty acid triglyceride (SSU) mass ratio of 9/1 or more, which comprises conducting transesterification of a fat and oil containing SUS of 50% by mass or more and SSU with an action of a 1,3-selective lipase selected from the group consisting of lipases derived from Thermomyces sp., Rhizopus oryzae and Rhizopus delemar. This process is an industrially suitable process for preparing a hard butter which has excellent properties as a cacao butter equivalent (CBE) or cacao butter improver (CBI).

  提供了一种用于制备 1,3-二饱和长链脂肪酸 2-单不饱和长链脂肪酸甘油三酯 （SUS）/1,2-二饱和长链脂肪酸 3-单不饱和长链脂肪酸甘油三酯（SSU）质量比为 9/1 或以上的油脂的工艺、其中包括在 1，3-选择性脂肪酶的作用下，对含有 SUS（质量分数为 50%或以上）和 SSU 的油脂进行酯交换反应，该脂肪酶选自热酵母菌（Thermomyces sp.,Rhizopus oryzae 和 Rhizopus delemar。该工艺是一种适用于工业化生产的硬黄油制备工艺，它作为可可黄油等同物（CBE）或可可黄油改良剂（CBI）具有极佳的特性。
• PROCESS FOR PRODUCING OIL-AND-FAT
  申请人：The Nisshin OilliO Group, Ltd.

  公开号：EP2404985A1

  公开（公告）日：2012-01-11

  The present invention discloses a method for producing fats and oils rich in a X2U triglyceride, which comprises the step of fractionating fats and oils which comprise 20 to 60 mass % of a di-saturated mono-unsaturated triglyceride (X2U triglyceride) consisting of two saturated fatty acid residues and one unsaturated fatty acid residue in total triglycerides in the presence of 1 to 50 mass % of a fatty acid lower alkyl ester comprising 10 to 100 mass % of an unsaturated fatty acid lower alkyl ester. This method is a more efficient and industrially suitable fractionation and production method of fats and oils rich in a di-saturated mono-unsaturated triglyceride (X2U triglyceride).

  本发明公开了一种生产富含 X2U 甘油三酯的油脂的方法、该方法包括以下步骤：在含有 1 至 50 质量％的脂肪酸低级烷基酯（其中 10 至 100 质量％为不饱和脂肪酸低级烷基酯）的情况下，分馏出在甘油三酯总量中含有 20 至 60 质量％的由两个饱和脂肪酸残基和一个不饱和脂肪酸残基组成的二饱和单不饱和甘油三酯（X2U 甘油三酯）的油脂。该方法是一种更高效、更适合工业化生产的富含二饱和单不饱和甘油三酯（X2U 甘油三酯）的油脂分馏和生产方法。