1.3-甘油二油酸酯 | 98168-52-6

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 1.3-甘油二油酸酯
• 中文别名: 二油酸甘油酯 9C 18:1；二油酸甘油酯9C18:1；二反油酸甘油酯 9C 18:1反；1,3-二发油酸甘油酯；二反油酸甘油酯；(Z)-9-十八烯酸与1,2,3-丙三醇的二酯；二油酸甘油酯；二反油酸甘油酯9C18:1反；二油酸甘油酯(游离油酸)
• 英文名称: 2-hydroxy-3-[(9E)-9-octadecenoyloxy]propyl (9E)-9-octadecenoate
• 英文别名: 1,3-dielaidin；[2-hydroxy-3-[(E)-octadec-9-enoyl]oxypropyl] (E)-octadec-9-enoate
• CAS: 98168-52-6；25637-84-7
• 化学式: C₃₉H₇₂O₅
• 分子量: 620.998
• InChiKey: DRAWQKGUORNASA-XPWSMXQVSA-N

物化性质

• 溶解度：
  DMF：10mg/mL；乙醇：10mg/mL；乙醇:PBS (pH 7.2) (1:1): 0.5 mg/mL
• 密度：
  0.89-0.92 g/cm3(Temp: 50 °C)
• 熔点：
  12 °C
• LogP：
  15.178 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  44
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

制备方法与用途

用途

二油酸甘油酯可用于治疗乳腺癌。

反应信息

• 作为反应物：
  描述：

  1.3-甘油二油酸酯 在 2,6-二甲基吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 51.0h， 生成 1,3-dielaidoyl-2-(4-iodobutanoyl)glycerol
  参考文献：
  名称：

  Symmetrical cationic triglycerides

  摘要：

  Some cationic triglycerides 1Aa-1Cb which have a symmetrical structure were effectively synthesized and formulated into cationic liposomes with the co-lipid dioleoylphosphatidylethanolamine (DOPE) and/or dilauroylphosphatidylcholine (DLPC). The plasmid encoding a luciferase was delivered into CHO cells by using these cationic liposomes. Our symmetrical cationic triglycerides showed high transfection activity when DOPE was used as a co-lipid. Among the symmetrical cationic triglycerides synthesized here, 1Ab and 1Ac, which have an oleoyl group at the 1- and 3-position in the glycerol backbone and also have a relatively long linker connecting the 2-hydroxy group in glycerol with the quaternary ammonium head group, were found to be the most suitable for gene delivery into cells. The transfection activity of the symmetrical cationic triglyceride 1Ab was comparable with that of its asymmetrical congener 6 and several times higher than that of Lipofectin(R). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00242-x
• 作为产物：
  描述：

  反油酸 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 20.33h， 生成 1.3-甘油二油酸酯
  参考文献：
  名称：

  Symmetrical cationic triglycerides

  摘要：

  Some cationic triglycerides 1Aa-1Cb which have a symmetrical structure were effectively synthesized and formulated into cationic liposomes with the co-lipid dioleoylphosphatidylethanolamine (DOPE) and/or dilauroylphosphatidylcholine (DLPC). The plasmid encoding a luciferase was delivered into CHO cells by using these cationic liposomes. Our symmetrical cationic triglycerides showed high transfection activity when DOPE was used as a co-lipid. Among the symmetrical cationic triglycerides synthesized here, 1Ab and 1Ac, which have an oleoyl group at the 1- and 3-position in the glycerol backbone and also have a relatively long linker connecting the 2-hydroxy group in glycerol with the quaternary ammonium head group, were found to be the most suitable for gene delivery into cells. The transfection activity of the symmetrical cationic triglyceride 1Ab was comparable with that of its asymmetrical congener 6 and several times higher than that of Lipofectin(R). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00242-x

文献信息

• 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。
• 一种1,2-二油酸甘油酯的制备方法
  申请人：南京威尔生物科技有限公司

  公开号：CN117623921A

  公开（公告）日：2024-03-01

  本发明涉及一种1,2‑二油酸甘油酯的制备方法。将油酸与甘油混合反应获取1,2‑二油酸甘油酯粗品后；将所述1,2‑二油酸甘油酯粗品投入硅胶层析柱中纯化，以正己烷‑乙酸乙酯作为洗脱液进行等度洗脱，收集洗脱液浓缩干燥，获取1,2‑二油酸甘油酯成品。本发明的制备方法工艺步骤简单，制得粗品后采用硅胶柱层析法精制纯化，并选用正己烷‑乙酸乙酯作为洗脱液，混合组分分离明显，收集1,2‑二油酸甘油酯洗脱部位，纯化得到的1,2‑二油酸甘油酯浓度不低于95％，方法容易操作且产物纯度高。
• Directed Interesterification in Glycerides. III. The Synthesis of Single-Fatty Acid 1,3-Diglycerides¹
  作者：Fred J. Baur、Willy Lange

  DOI：10.1021/ja01152a109

  日期：1951.8
• Synthesis and Physical Properties of EOE and EEO, Triacylglycerols Containing Elaidic and Oleic Fatty Acids
  作者：R. O. Adlof、G. R. List

  DOI：10.1007/s11746-007-1056-2

  日期：2007.5.10

  AbstractSymmetrical and non‐symmetrical triacylglycerols (TAG) containing oleic (O; 9c‐18:1) and elaidic (E; 9t‐18:1) acids were required as part of a study relating the physical characteristics and functionality of trans‐containing TAG with the mouth feel, taste characteristics and related characteristics desired by consumers in frying oils and pastries. To replace the trans isomers in frying oils—a significant part of frying oils prepared by partial hydrogenation of vegetable oils—without loss of the sensory properties desired by consumers, required the initiation of a study relating the structure of trans‐containing TAG with such characteristics as melting range, drop points, and other crystalline properties. Elaidic acid was esterified to trielaidin (EEE), and the EEE partially converted (glycerol/p‐toluenesulfonic acid) to a mixture containing ca. 40% DAG (the 1,3‐ and 1,2‐isomers). The DAG fraction was separated by silica gel chromatography, the 1,3‐dielaidylglycerol (1,3EE‐DAG) isomer isolated (structural purity >99%) by crystallization from acetone and esterified with oleic acid (O) to yield EOE. The 1(3)O‐MAG was purchased commercially and esterified with E acid to prepare OEE. Both syntheses yielded multi‐gram quantities of EOE and EEO, in 80–85% yields, and with structural purities >99%. Thus, by careful selection of the thermodynamically more‐stable MAG or DAG precursors, the symmetrical EOE and non‐symmetrical EEO isomers could be readily synthesized, and their drop point and melting point values determined.
• Carter; Malkin, Journal of the Chemical Society, 1947, p. 555
  作者：Carter、Malkin

  DOI：——

  日期：——