1-oleoyl-2,3-dipalmitoyl-sn-glycerol | 53023-10-2

• 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-oleoyl-2,3-dipalmitoyl-sn-glycerol
• 英文别名: 1-Palmitoyl-2-palmitoyl-3-oleoyl-glycerol；[(2S)-2,3-di(hexadecanoyloxy)propyl] (Z)-octadec-9-enoate
• CAS: 53023-10-2
• 化学式: C₅₃H₁₀₀O₆
• 分子量: 833.373
• InChiKey: YHMDGPZOSGBQRH-OIVKDUIRSA-N

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

反应信息

• 作为产物：
  描述：

  1-O-benzyl-2,3-di-O-hexadecanoyl-sn-glycerol 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 2.0h， 生成 1-oleoyl-2,3-dipalmitoyl-sn-glycerol
  参考文献：
  名称：

  对映体结构化的三酰基甘油的合成

  摘要：

  描述了九种AAB型对映纯结构化的三酰基甘油（TAGs）的合成，它们都具有（S）绝对构型。其中六个具有一个饱和和两个相同的不饱和脂肪酰基链，而其余三个具有两个相同的饱和脂肪酸以及一个不饱和脂肪酸。前一组是通过五步化学酶法合成的，涉及从对映体（R）-solketal开始的高度区域选择性固定化南极假丝酵母脂肪酶。第二组是基于相同的手性前体，通过完全化学五步法制备的。强烈要求将此类对映纯TAG作为对油脂中完整TAG进行对映特异性分析的标准。

  DOI：

  10.1016/j.tetasy.2013.11.015

文献信息

• Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1039/b713246h

  日期：——

  acyl residue at the central carbon of the silylated synthons with a subsequent Et(3)N.3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment

  三氟乙酸催化带有三氟乙酸酐（TFAA）的带有烯丙基酰基或烷基官能团的缩水甘油基衍生物的环氧乙烷环的开环，可有效进入构型均质的1（3）-酰基-或1（3）-O-烷基-sn -甘油。在这些关键中间体的末端位置选择性引入叔丁基二甲基甲硅烷基-（TBDMS）或三异丙基甲硅烷基-（TIPS）瞬态保护可确保1（3）-酰基-或1（3）-O-烷基-3（1）- O-TBDMS（或TIPS）-sn-甘油作为1,2（2,3）-二酰基-，1（3）-O-烷基-2-酰基-和1,3-二酰基-sn-的一般双功能前体甘油和三酯等排体。通过三氯乙酸酐（TCAA）在甲硅烷基化的合成子的中央碳原子上引入必要的酰基残基，并随后进行Et（3）N.3HF促进的，直接的三氯乙酰化作用穿过硅烷氧基体系 然后裂解三氯乙酰基，得到各自的1,2（2,3）-二酰基-或1（3）-O-烷基-2-酰基-sn-甘油。可选择地，反应序列包括：（i）三氯乙酰基片段连接在单甲硅烷基化甘油酯的立体C
• METHOD FOR ANALYZING TRIGLYCERIDE, METHOD FOR SEPARATING OIL AND FAT, AND METHOD FOR MANUFACTURING TRIGLYCERIDE
  申请人：The Nisshin OilliO Group, Ltd.

  公开号：EP3783358A1

  公开（公告）日：2021-02-24

  An object of the present invention is to provide a method for analyzing an isomer of triglyceride, a method for sorting oils and fats having different contents of an isomer of triglyceride, and a method for producing triglyceride of which an isomer can be fractionated. The present invention is a method for analyzing triglyceride, including a step of analyzing an isomer of triglyceride by supercritical fluid chromatography, in which multiple types of stationary phases are used in the supercritical liquid chromatography, and at least two stationary phases among the stationary phases have different chiral selectors in each of which one or more chlorines are bound to a polysaccharide derivative.

  本发明的目的是提供一种分析甘油三酯异构体的方法、一种对具有不同甘油三酯异构体含量的油脂进行分选的方法，以及一种生产可对其异构体进行分馏的甘油三酯的方法。本发明是一种分析甘油三酯的方法，包括通过超临界流体色谱法分析甘油三酯异构体的步骤，在超临界液相色谱法中使用多种类型的固定相，其中至少两种固定相具有不同的手性选择器，每种手性选择器中都有一个或多个氯与多糖衍生物结合。
• Enantioselective chromatography in analysis of triacylglycerols common in edible fats and oils
  作者：Marika Kalpio、Matts Nylund、Kaisa M. Linderborg、Baoru Yang、Björn Kristinsson、Gudmundur G. Haraldsson、Heikki Kallio

  DOI：10.1016/j.foodchem.2014.09.135

  日期：2015.4

  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.
• Tattrie et al., Archives of Biochemistry, 1958, vol. 78, p. 319,320
  作者：Tattrie et al.

  DOI：——

  日期：——
• METHOD FOR ANALYZING TRIGLYCERIDE, METHOD FOR SORTING OIL AND FAT, AND METHOD FOR PRODUCING TRIGLYCERIDE
  申请人：THE NISSHIN OILLIO GROUP, LTD.

  公开号：US20210102923A1

  公开（公告）日：2021-04-08

  An object of the present invention is to provide a method for analyzing an isomer of triglyceride, a method for sorting oils and fats having different contents of an isomer of triglyceride, and a method for producing triglyceride of which an isomer can be fractionated. The present invention is a method for analyzing triglyceride, including a step of analyzing an isomer of triglyceride by supercritical fluid chromatography, in which multiple types of stationary phases are used in the supercritical liquid chromatography, and at least two stationary phases among the stationary phases have different chiral selectors in each of which one or more chlorines are bound to a polysaccharide derivative.