α,β-glycerol diundecenoate | 1222191-68-5

• 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: α,β-glycerol diundecenoate
• 英文别名: 1,2-di-10-undecenoylglycerol；glycerol α,β-diundecenoate；α,β-GDU；(3-Hydroxy-2-undec-10-enoyloxypropyl) undec-10-enoate
• CAS: 1222191-68-5
• 化学式: C₂₅H₄₄O₅
• 分子量: 424.621
• InChiKey: HNOJSYCUUNANIX-UHFFFAOYSA-N

物化性质

• 沸点：
  514.3±30.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-((4-methoxybenzyl)oxy)propane-1,2-diyl bis(undec-10-enoate) 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 α,α'-glycerol diundecenoate 、 α,β-glycerol diundecenoate
  参考文献：
  名称：

  Next generation macrocyclic and acyclic cationic lipids for gene transfer: Synthesis and in vitro evaluation

  摘要：

  Previously we reported the synthesis and in vitro evaluation of four novel, short-chain cationic lipid gene delivery vectors, characterized by acyclic or macrocyclic hydrophobic regions composed of, or derived from, two 7-carbon chains. Herein we describe a revised synthesis of an expanded library of related cationic lipids to include extended chain analogues, their formulation with plasmid DNA (pDNA) and in vitro delivery into Chinese hamster ovarian (CHO-K1) cells. The formulations were evaluated against each other based on structural differences in the hydrophobic domain and headgroup. Structurally the library is divided into four sets based on lipids derived from two 7- or two 11-carbon hydrophobic chains, C7 and C11 respectively, which possess either a dimethylamine or a trimethylamine derived headgroup. Each set includes four cationic lipids based on an acyclic or macrocyclic, saturated or unsaturated hydrophobic domain. All lipids were co-formulated with the commercial cationic lipid 1,2-dimyristoyl-sn-glycero-3-ethylphosphocholine (EPC) in a 1:1 molar ratio, along with one of two distinct neutral co-lipids, cholesterol or 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) in an overall cationic-to-neutral lipid molar ratio of 3:2. Binding of lipid formulations with DNA, and packing morphology associated with the individual lipid-DNA complexes were characterized by gel electrophoresis and small angle X-ray diffraction (SAXD), respectively. As a general trend, lipoplex formulations based on mismatched binary cationic lipids, composed of a shorter C7 lipid and the longer lipid EPC (C14), were generally associated with higher transfection efficiency and lower cytotoxicity than their more closely matched C11/EPC binary lipid formulation counterparts. Furthermore, the cyclic lipids gave transfection levels as high as or greater than their acyclic counterparts, and formulations with cholesterol exhibited higher transfection and lower cytotoxicity than those formulated with DOPE. A number of the lipid formulations with cholesterol as co-lipid performed as well as, or better than Lipofectamine 2000 (TM) and EPC, the two positive controls employed in these studies. These results suggest that our novel cyclic and acyclic cationic lipid vectors are effective nonviral gene transfer agents that warrant further investigation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.032

文献信息

• Structural Analysis of Partial and Total Esters of Glycerol Undecenoate and Diglycerol Undecenoate
  作者：Gildas Nyame Mendendy Boussambe、Romain Valentin、Zéphirin Mouloungui

  DOI：10.1007/s11746-015-2725-1

  日期：2015.12

  composition of esters of undecylenic acid formed with glycerol or diglycerol as a function of their reaction conditions, which constitute a highly complex system. We purified undecylenic acid esters from each polyol family to allow the structural identification of each ester of glycerol and each ester of diglycerol with undecylenic acid. We found that the polarity of these non‐ionic amphiphilic esters directly

  甘油和十一碳烯酸之间或二甘油和十一碳烯酸之间的直接酯化反应产生所有可能类型的甘油或二甘油酯。通过硅胶色谱法纯化，从而以纯净形式分离出每种类型的酯。通过质谱，1 H NMR，13表征并鉴定了分离出的化合物的分子结构C NMR和DEPT-135。然后，我们研究了与甘油或二甘油形成的十一碳烯酸酯的组成，并根据它们的反应条件而定，它们构成了一个高度复杂的系统。我们从每个多元醇家族中纯化十一碳烯酸酯，以使每个甘油酯和二甘油与十一碳烯酸酯的结构鉴定成为可能。我们发现这些非离子两亲酯的极性直接影响它们对有机和无机溶剂的亲和力，并且这些酯的行为与阴离子两亲分子（如十一碳烯酸）有很大不同。
• Phosphorus-containing renewable polyester-polyols via ADMET polymerization: Synthesis, functionalization, and radical crosslinking
  作者：Lucas Montero de Espinosa、Michael A. R. Meier、Juan C. Ronda、Marina Galià、Virginia Cádiz

  DOI：10.1002/pola.23887

  日期：2010.4.1

  acyclic diene metathesis copolymerization (ADMET) of this monomer with a phosphorus‐containing α,ω‐diene (DOPO II), also plant oil derived, afforded a series of phosphorus containing linear polyesters, which have been fully characterized. The backbone hydroxyls of these polyesters have been acrylated and radically polymerized to produce crosslinked polymers. The thermomechanical and mechanical properties

  由植物油衍生的平台化学品制备了含羟基的α，ω-二烯。该单体与也由植物油衍生的含磷α，ω-二烯（DOPO II）的无环二烯复分解共聚（ADMET）提供了一系列含磷线性聚酯，这些聚酯已得到充分表征。这些聚酯的主链羟基已被丙烯酸酯化并自由基聚合以产生交联的聚合物。对这些磷基热固性塑料的热机械和机械性能，热稳定性和阻燃性进行了研究。此外，在选定的ADMET聚合反应中，将10-十一碳烯酸甲酯用作链终止剂，以研究预聚物分子量对最终材料不同性能的影响。分级为4 +©2010 Wiley Periodicals，Inc.
• US4333987A
  申请人：——

  公开号：US4333987A

  公开（公告）日：1982-06-08
• Next generation macrocyclic and acyclic cationic lipids for gene transfer: Synthesis and in vitro evaluation
  作者：Emile Jubeli、Amanda B. Maginty、Nada Abdul Khalique、Liji Raju、Mohamad Abdulhai、David G. Nicholson、Helge Larsen、Michael D. Pungente、William P.D. Goldring

  DOI：10.1016/j.bmc.2015.08.032

  日期：2015.10

  Previously we reported the synthesis and in vitro evaluation of four novel, short-chain cationic lipid gene delivery vectors, characterized by acyclic or macrocyclic hydrophobic regions composed of, or derived from, two 7-carbon chains. Herein we describe a revised synthesis of an expanded library of related cationic lipids to include extended chain analogues, their formulation with plasmid DNA (pDNA) and in vitro delivery into Chinese hamster ovarian (CHO-K1) cells. The formulations were evaluated against each other based on structural differences in the hydrophobic domain and headgroup. Structurally the library is divided into four sets based on lipids derived from two 7- or two 11-carbon hydrophobic chains, C7 and C11 respectively, which possess either a dimethylamine or a trimethylamine derived headgroup. Each set includes four cationic lipids based on an acyclic or macrocyclic, saturated or unsaturated hydrophobic domain. All lipids were co-formulated with the commercial cationic lipid 1,2-dimyristoyl-sn-glycero-3-ethylphosphocholine (EPC) in a 1:1 molar ratio, along with one of two distinct neutral co-lipids, cholesterol or 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) in an overall cationic-to-neutral lipid molar ratio of 3:2. Binding of lipid formulations with DNA, and packing morphology associated with the individual lipid-DNA complexes were characterized by gel electrophoresis and small angle X-ray diffraction (SAXD), respectively. As a general trend, lipoplex formulations based on mismatched binary cationic lipids, composed of a shorter C7 lipid and the longer lipid EPC (C14), were generally associated with higher transfection efficiency and lower cytotoxicity than their more closely matched C11/EPC binary lipid formulation counterparts. Furthermore, the cyclic lipids gave transfection levels as high as or greater than their acyclic counterparts, and formulations with cholesterol exhibited higher transfection and lower cytotoxicity than those formulated with DOPE. A number of the lipid formulations with cholesterol as co-lipid performed as well as, or better than Lipofectamine 2000 (TM) and EPC, the two positive controls employed in these studies. These results suggest that our novel cyclic and acyclic cationic lipid vectors are effective nonviral gene transfer agents that warrant further investigation. (C) 2015 Elsevier Ltd. All rights reserved.