sn-1,2-dioleoyl-3-palmitoylglycerol | 14863-26-4

• 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: sn-1,2-dioleoyl-3-palmitoylglycerol
• 英文别名: 3-hexadecanoyl-1,2-di(cis-octadec-9-enoyl)-sn-glycerol；1,2-dioleoyl-3-palmitoylglycerol；1,2-Dioleoyl-3-palmitoyl-sn-glycerol；[(2S)-3-hexadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• CAS: 14863-26-4
• 化学式: C₅₅H₁₀₂O₆
• 分子量: 859.411
• InChiKey: JFISYPWOVQNHLS-HMOYFKASSA-N

物化性质

• 沸点：
  802.2±45.0 °C(Predicted)
• 密度：
  0.919±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)
• 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

反应信息

• 作为反应物：
  描述：

  sn-1,2-dioleoyl-3-palmitoylglycerol 、 水 生成 oleate 、 1-oleoyl-3-palmitoyl-sn-glycerol 、 氢(+1)阳离子
  参考文献：
  名称：

  Studies on the Substrate and Stereo/Regioselectivity of Adipose Triglyceride Lipase, Hormone-sensitive Lipase, and Diacylglycerol-O-acyltransferases

  摘要：

  Adipose triglyceride lipase (ATGL) is rate-limiting for the initial step of triacylglycerol (TAG) hydrolysis, generating diacylglycerol (DAG) and fatty acids. DAG exists in three stereochemical isoforms. Here we show that ATGL exhibits a strong preference for the hydrolysis of long-chain fatty acid esters at the sn-2 position of the glycerol backbone. The selectivity of ATGL broadens to the sn-1 position upon stimulation of the enzyme by its co-activator CGI-58. sn-1,3 DAG is the preferred substrate for the consecutive hydrolysis by hormone-sensitive lipase. Interestingly, diacylglycerol-O-acyltransferase 2, present at the endoplasmic reticulum and on lipid droplets, preferentially esterifies sn-1,3 DAG. This suggests that ATGL and diacylglycerol-O-acyltransferase 2 act coordinately in the hydrolysis/re-esterification cycle of TAGs on lipid droplets. Because ATGL preferentially generates sn-1,3 and sn-2,3, it suggests that TAG-derived DAG cannot directly enter phospholipid synthesis or activate protein kinase C without prior isomerization.

  DOI：

  10.1074/jbc.m112.400416
• 作为产物：
  描述：

  1-Benzyl-glycerin-3-palmitinsaeureester 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 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、500.01 kPa 条件下， 反应 2.0h， 生成 sn-1,2-dioleoyl-3-palmitoylglycerol
  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

• 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.
• Kawasaki T.; Snyder F., J Biol Chem, 1988, 0021-9258, 2593-6
  作者：Kawasaki T.、Snyder F.

  DOI：——

  日期：——
• A human skin multifunctional O-acyltransferase that catalyzes the synthesis of acylglycerols, waxes, and retinyl esters
  作者：Chi-Liang Eric Yen、Charles H. Brown、Mara Monetti、Robert V. Farese

  DOI：10.1194/jlr.m500168-jlr200

  日期：2005.11

  Acyl-CoA-dependent O-acyltransferases catalyze reactions in which fatty acyl-CoAs are joined to acyl acceptors containing free hydroxyl groups to produce neutral lipids. In this report, we characterize a human multifunctional O-acyltransferase (designated MFAT) that belongs to the acyl-CoA: diacylglycerol acyltransferase 2/acyl-CoA: monoacylglycerol acyltransferase (MGAT) gene family and is highly expressed in the skin. Membranes of insect cells and homogenates of mammalian cells overexpressing MFAT exhibited significantly increased MGAT, acyl-CoA: fatty acyl alcohol acyltransferase (wax synthase), and acyl-CoA: retinol acyltransferase (ARAT) activities, which catalyze the synthesis of diacylglycerols, wax monoesters, and retinyl esters, respectively. Furthermore, when provided with the appropriate substrates, intact mammalian cells overexpressing MFAT accumulated more waxes and retinyl esters than control cells. We conclude that MFAT is a multifunctional acyltransferase that likely plays an important role in lipid metabolism in human skin.
• Saccharomyces cerevisiae phospholipid:diacylglycerol acyl transferase (PDAT) devoid of its membrane anchor region is a soluble and active enzyme retaining its substrate specificities
  作者：Alokesh Ghosal、Antoni Banas、Ulf Ståhl、Anders Dahlqvist、Ylva Lindqvist、Sten Stymne

  DOI：10.1016/j.bbalip.2007.10.007

  日期：2007.12

  A N-terminal deleted version of the Saccharomyces cerevisiae phospholipid:diacylglycerol acyltransferase (ScPDAT), lacking the predicted membrane-spanning region, was fused in frame with alpha-factor secretion signal and expressed in Pichia pastoris under the control of the methanol inducible alcohol oxidase promoter. This resulted in a truncated, soluble and highly active PDAT protein secreted into the culture medium of the recombinant cells. The soluble as well as native membrane bound enzymes was shown to be glycosylated and extensive deglycosylation severely lowered the activity. The production of a soluble and extracellular PDAT allowed us to investigate substrate preferences of the enzyme without interference of endogenous lipids and enzymes. Similar to the membrane bound counterpart, the highest activity was achieved with acyl groups at sn-2 position of phosphatidylethanolamine as acyl donor and 1,2-diacylglycerols as acyl acceptor. The soluble enzyme was also able to catalyze, at a low rate, a number of transacylation reactions between various neutral lipids and between polar lipids and neutral lipids others than diacylglycerols, including acylation of long chain alcohols. (c) 2007 Elsevier B.V. All rights reserved.