(甲基亚胺)二-2,1-乙二基二十六烷酸酯 | 88703-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (甲基亚胺)二-2,1-乙二基二十六烷酸酯
• 中文别名: N-[2-(二甲氨基)乙基]-5-[(Z)-(5-氟-2-羰基-1,2-二氢-3H-吲哚-3-亚基)甲基]-2,4-二甲基-1H-吡咯-3-甲酰胺
• 英文名称: N-methyl-di-O-palmitoylethanolamine
• 英文别名: (Methylimino)diethane-2,1-diyl dipalmitate；2-[2-hexadecanoyloxyethyl(methyl)amino]ethyl hexadecanoate
• CAS: 88703-86-0
• 化学式: C₃₇H₇₃NO₄
• 分子量: 595.991
• InChiKey: CBNRTKLQURDWHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  42
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  (甲基亚胺)二-2,1-乙二基二十六烷酸酯 、 碘甲烷 以 乙腈 为溶剂， 反应 1.0h， 生成 N,N-di(2-hexadecanoyloxyethyl)dimethylammonium iodide
  参考文献：
  名称：

  Preparation and Characterization of Phase-Segregated Vesicles of Photopolymerizable Diacetylene Mixed with Nonpolymerizable Amphiphiles

  摘要：

  将 1,2-二（十六烷氧基羰基）乙烷磺酸钠（2C16S）与可光聚合的 1,2-二（10,12-三缩水甘油酰）-sn-甘油 3-磷酸胆碱（DTPC）按 2:100 的比例混合，通过改良薄膜水合法处理，得到一种聚合体，在 254 纳米波长的照射下，聚合体变成了巨囊（GVs）。用激光共聚焦扫描显微镜分析了 GVs 横截面上的自发荧光，发现其呈直径为 3.8 微米的环形，环内存在约 1 微米的暗色部分。当十八烷基罗丹明 B（RhB）作为两亲性荧光探针加入龙胆紫时，RhB 的荧光从整个环中发射出来。因此，2C16S 与 DTPC 的相分离得到了证实。同样，在 N,N-二（2-十六碳酰氧基乙基）二甲基碘化铵与 DTPC 的混合囊泡中发现，相分离囊泡的直径为 3.7 微米，在横截面图像中，环上有约 1 微米的暗色部分。另一方面，与 1,2-二（十二烷氧基羰基）乙磺酸盐、N,N-二（2-十二烷酰氧乙基）二甲基碘化铵和 N,N-二（2-十四烷酰氧乙基）二甲基碘化铵混合的 DTPC 囊泡形成了球状结构，充满了囊泡内部。每种双亲化合物主要相变温度的差异解释了分离机制。

  DOI：

  10.1246/bcsj.20100192
• 作为产物：
  描述：

  N-甲基二乙醇胺 、 棕榈酰氯 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (甲基亚胺)二-2,1-乙二基二十六烷酸酯
  参考文献：
  名称：

  Novel Series of Non-Glycerol-Based Cationic Transfection Lipids for Use in Liposomal Gene Delivery

  摘要：

  A novel series of nontoxic and non-glycerol-based simple monocationic transfection lipids containing one or two hydroxyethyl groups directly linked to the positively charged nitrogen atom were synthesized. The in vitro transfection efficiencies of these new liposomal gene delivery reagents were better than that of lipofectamine, a widely used transfection agent in cationic lipid-mediated gene transfer. The most efficient transfection formulation was observed to be a 1:1:0.3 mol ratio of DHDEAB (N,N-di-n-hexadecyl-N,N-dihydroxyethylammonium bromide): cholesterol:HDEAB (N-n-hexadecyl-N,N-dihydroxyethylammonium bromide) using a DHDEAB-to-DNA charge ratio (+/-) of 0.3:1. Observation of good transfection at charge ratios lower than 1 suggests that the amphiphile-DNA complex may have net negative charge. Our results reemphasize the important point that in cationic lipid-mediated gene delivery, the overall charge of the lipid-DNA complex need not always be positive. In addition, our transfection results also imply that favorable hydrogen-bonding interactions between the lipid headgroups and the cell surface of biological membranes may have some role for improving the transfection efficiency in cationic lipid-mediated gene delivery.

  DOI：

  10.1021/jm9806446

文献信息

• [EN] POLYAMINE-FATTY ACID DERIVED LIPIDOIDS AND USES THEREOF<br/>[FR] LIPIDOÏDES DÉRIVÉS DE POLYAMINE-ACIDE GRAS ET LEURS UTILISATIONS
  申请人：MASSACHUSETTS INST TECHNOLOGY

  公开号：WO2016004202A1

  公开（公告）日：2016-01-07

  The present disclosure provides polyamine-fatty acid derived lipidoids (e.g., compounds of Formula (I) or (II)) and methods of preparing the lipidoids. A described lipidoid includes R-C(=0)-0- moieties (where R is a lipid moiety), which may be hydrolyzed into non-toxic fatty acids. Also provided are compositions including a described lipidoid and an agent (e.g., polynucleotide, small molecule, peptide, or protein). The present disclosure also provides methods, kits, and uses that involve the lipidoids or compositions for delivering an agent to a subject, tissue, or cell and/or for treating and/or preventing a range of diseases, such as genetic diseases, proliferative diseases, hematological diseases, neurological diseases, immunological diseases, gastrointestinal diseases, respiratory diseases, painful conditions, psychiatric disorders, and metabolic disorders.

  本公开提供了聚胺脂肪酸衍生的脂质体（例如，化合物的化学式（I）或（II））以及制备脂质体的方法。所述脂质体包括R-C(=0)-0-基团（其中R是脂质基团），可以水解为无毒脂肪酸。还提供了包括所述脂质体和药剂（例如，多核苷酸、小分子、肽或蛋白质）的组合物。本公开还提供了涉及脂质体或组合物用于将药剂传递给受体、组织或细胞和/或用于治疗和/或预防一系列疾病的方法、试剂盒和用途，例如遗传疾病、增殖性疾病、血液疾病、神经系统疾病、免疫系统疾病、胃肠道疾病、呼吸系统疾病、疼痛症状、精神障碍和代谢性疾病。
• Synthesis, Surface Properties, and Antibacterial Activity of Novel Ester‐Containing Cationic Silicone Surfactants and Their Utilization as Fabric‐Finishing Agents
  作者：Yuan Wei、Cheng Zheng、Zhenqiang Zhang、Zhaowen Zeng、Taoyan Mao、Shikang Long、Hui Ling

  DOI：10.1002/jsde.12211

  日期：2019.3

  In this study, a series of cationic silicone surfactants SiQCnCl containing ester groups and double long‐chain alkyls (n = 9, 11, 13, 15, and 17) were synthesized by microwave irradiation and characterized using infrared Fourier transform (FTIR), 1H nuclear magnetic resonance (1H NMR), and thermogravimetric analysis (TGA). Surface activity and adsorption of these surfactants were investigated by measuring

  在这项研究中，通过微波辐射合成了一系列包含酯基和双长链烷基（n = 9、11、13、15和17）的阳离子硅表面活性剂SiQC n Cl ，并使用红外傅里叶变换（FTIR）进行了表征，1 H核磁共振（1 H NMR）和热重分析（TGA）。通过测量平衡表面张力来研究这些表面活性剂的表面活性和吸附。临界胶束浓度（CMC）随着SiQC的烷基长度减小Ñ在25℃Cl和所以没有在CMC中的对应的表面张力（γ CMC）。还通过透射电子显微镜（TEM）和动态光散射（DLS）系统研究了水溶液中的聚集行为。观察到直径为300至900 nm的球形或椭圆形聚集体。研究还表明，阳离子有机硅表面活性剂对金黄色葡萄球菌表现出一定的抗菌作用，但对大肠杆菌的作用稍差。SiQC 15的形态结构使用扫描电子显微镜（SEM）观察了用Cl处理过的棉织物，结果表明表面变得整洁光滑。而且，成品棉织物保持了一些抗菌性能并改善了柔软度，可以
• Polymeric surfactant vesicles. Synthesis and characterization by nuclear magnetic resonance spectroscopy and dynamic laser light scattering
  作者：Donald Kippenberger、Kenneth Rosenquist、Lars Odberg、Pietro Tundo、Janos H. Fendler

  DOI：10.1021/ja00343a011

  日期：1983.3

  3/(CH/sub 2/)/sub 17/)NCOCH==CHCO/sub 2/H(4) have been synthesized. Sonication of these surfactants led to the formation of vesicles. Vesicles could be polymerized by exposure to ultraviolet radiation or by the use of azoisobutyronitrile (AIBN) as an initiator. Vesicles prepared from 1 polymerized in their bilayers. Vesicles prepared from 2, 3, and 4 have double bonds on their headgroups and could, therefore

  (CH/sub 3/(CH/sub 2/)/sub 15/)(CH/sub 2/==CH(CH/sub 2/)/sub 8/CONH(CH/sub 2/)/sub 6/ )(CH/sub 3/)/sub 2/N/sup +/Br/sup -/(1),(CH/sub 3/(CH/sub 2/)/sub 14/CO/sub 2/(CH) /sub 2/)/sub 2/)/sub 2/(CH/sub 3/)(CH/sub 2/CH==CH/sub 2/)N/sup +/Br/sup -/(2), (CH/sub 3/(CH/sub 2/)/sub 14/CO/sub 2/(CH/sub 2/)/sub 2/)/sub 2/NCOCH==CHCO/sub 2/H(3) , 和 (CH/sub 3/(CH/sub 2/)/sub 17/)NCOCH==CHCO/sub 2/H(4) 已经合成。这些表
• Production of N‐methyldiethanolamine di‐ester via heterogeneous transesterification of palm methyl ester over modified calcium oxide catalyst by metal oxides
  作者：Haliza Abdul Aziz、Rozita Yusoff、Ngoh Gek Cheng、Zainab Idris、Nur Aainaa Syahirah Ramli

  DOI：10.1002/jsde.12648

  日期：——

  through catalyst reuse. Calcium oxide (CaO)-based catalysts which include pure CaO and modified CaO by other metal oxides were employed in this study for the production of alkanolamine ester, a precursor of esterquats. The basicity and textural properties of these catalysts were characterized using TPD-CO2 and N2 physisorption, respectively. Transesterification activity of CaO-based catalysts successfully

  用于生产酯季铵盐前体的甲酯和烷醇胺的非均相催化酯交换反应的生产循环可以被认为是一种更清洁和可持续的工艺。与传统的均相催化相比，该过程是一种重要的替代路线，因为它可以消除废水的形成，消耗较少的有毒化学品，并通过催化剂的重复使用来降低生产成本。本研究采用氧化钙 (CaO) 基催化剂（包括纯 CaO 和其他金属氧化物改性的 CaO）来生产链烷醇胺酯（酯季铵盐的前体）。使用 TPD-CO 2和 N 2表征这些催化剂的碱度和结构性质分别为物理吸附。CaO基催化剂的酯交换活性在160°C、80 mbar、催化剂用量4 wt%、反应时间6 h、棕榈酸甲酯与N-甲基二乙醇胺摩尔比为2时成功表现出超过85%的高二酯收率：1且搅拌速度为150rpm。ZnO/CaO 催化剂呈现出最佳的耐久性特性，因为它在后续的三个运行中表现出恒定的活性，二酯产率为 85%。ZnO/CaO 显示出与纯 CaO 催化剂相似的高催化活性，Ca
• POLYAMINE-FATTY ACID DERIVED LIPIDOIDS AND USES THEREOF
  申请人：Massachusetts Institute of Technology

  公开号：US20160002178A1

  公开（公告）日：2016-01-07

  The present disclosure provides polyamine-fatty acid derived lipidoids (e.g., compounds of Formula (I) or (II)) and methods of preparing the lipidoids. A described lipidoid includes R—C(═O)—O— moieties (where R is a lipid moiety), which may be hydrolyzed into non-toxic fatty acids. Also provided are compositions including a described lipidoid and an agent (e.g., polynucleotide, small molecule, peptide, or protein). The present disclosure also provides methods, kits, and uses that involve the lipidoids or compositions for delivering an agent to a subject, tissue, or cell and/or for treating and/or preventing a range of diseases, such as genetic diseases, proliferative diseases, hematological diseases, neurological diseases, immunological diseases, gastrointestinal diseases, respiratory diseases, painful conditions, psychiatric disorders, and metabolic disorders.