1,8-bis(dodecyloxymethyl)-3,6-dioxaoctane-1,8-diol | 180284-34-8

• 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: 1,8-bis(dodecyloxymethyl)-3,6-dioxaoctane-1,8-diol
• 英文别名: 1-Dodecoxy-3-[2-(3-dodecoxy-2-hydroxypropoxy)ethoxy]propan-2-ol；1-dodecoxy-3-[2-(3-dodecoxy-2-hydroxypropoxy)ethoxy]propan-2-ol
• CAS: 180284-34-8
• 化学式: C₃₂H₆₆O₆
• 分子量: 546.872
• InChiKey: SZDLSIHMPRKELR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  38
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,8-bis(dodecyloxymethyl)-3,6-dioxaoctane-1,8-diol 、 2,3,4,6-四-O-乙酰基-Β-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-[1-dodecoxy-3-[2-[3-dodecoxy-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropoxy]ethoxy]propan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  A Novel Type of Highly Effective Nonionic Gemini Alkyl O-Glucoside Surfactants: A Versatile Strategy of Design

  摘要：

  A novel type of highly effective gemini alkyl glucosides has, been rationally designed and synthesized The gemini surfactants have been readily prepared. by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery.

  DOI：

  10.1021/la401569n
• 作为产物：
  描述：

  乙二醇二缩水甘油醚 、 十二烷醇 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以360 mg的产率得到1,8-bis(dodecyloxymethyl)-3,6-dioxaoctane-1,8-diol
  参考文献：
  名称：

  用没食子酸和十二烷基双子链开发用于水包油乳液的双子界面抗氧化剂。

  摘要：

  在这项研究中，通过使用预填充柱和蠕动泵为基础的纯化系统，通过使用没食子酸和十二烷基双基尼链的Steglich酯化，开发了用于水包油（O / W）乳液的双基没食子酸酯（GG）界面抗氧化剂。制备的GG和单没食子酸酯（MG​​）的结构特征和纯度通过NMR，傅里叶变换红外光谱和高效液相色谱-质谱法得到证实。进一步的评价表明，相对于MG，GG在O / W乳液中具有优异的自由基清除活性和优异的抗氧化活性，尤其是在乳化剂的量减少的条件下。通过荧光探针和透射电子显微镜（TEM）进行的显微镜研究表明，由于独特的双子分子结构，O / W乳液中出色的抗氧化性能可能归因于优选的界面位置。双子抗氧化剂的优异抗氧化活性为O / W乳液中的抗氧化提供了广阔前景。

  DOI：

  10.1021/acs.jafc.0c00807

文献信息

• Development of a Gemini Interfacial Antioxidant for Oil in Water Emulsion with Gallic Acid and Dodecyl Gemini Chains
  作者：Peifei Wang、Songbai Liu

  DOI：10.1021/acs.jafc.0c00807

  日期：2020.9.16

  In this study, development of the gemini gallate (GG) interfacial antioxidant for oil in water (O/W) emulsion was performed employing Steglich esterification with gallic acid and dodecyl gemini chains through a prepacked column and peristaltic pump-based purification system. The structural identity and purity of the prepared GG and monogallate (MG) were confirmed by NMR, Fourier transform infrared

  在这项研究中，通过使用预填充柱和蠕动泵为基础的纯化系统，通过使用没食子酸和十二烷基双基尼链的Steglich酯化，开发了用于水包油（O / W）乳液的双基没食子酸酯（GG）界面抗氧化剂。制备的GG和单没食子酸酯（MG​​）的结构特征和纯度通过NMR，傅里叶变换红外光谱和高效液相色谱-质谱法得到证实。进一步的评价表明，相对于MG，GG在O / W乳液中具有优异的自由基清除活性和优异的抗氧化活性，尤其是在乳化剂的量减少的条件下。通过荧光探针和透射电子显微镜（TEM）进行的显微镜研究表明，由于独特的双子分子结构，O / W乳液中出色的抗氧化性能可能归因于优选的界面位置。双子抗氧化剂的优异抗氧化活性为O / W乳液中的抗氧化提供了广阔前景。
• A Novel Type of Highly Effective Nonionic Gemini Alkyl <i>O</i>-Glucoside Surfactants: A Versatile Strategy of Design
  作者：Songbai Liu、Ruocheng Sang、Shan Hong、Yujing Cai、Hua Wang

  DOI：10.1021/la401569n

  日期：2013.7.9

  A novel type of highly effective gemini alkyl glucosides has, been rationally designed and synthesized The gemini surfactants have been readily prepared. by glycosylation of the gemini alkyl chains that are synthesized with regioselective ring-opening of ethylene glycol epoxides by the alkyl alcohols. The new gemini alkyl glucosides exhibit significantly better surface activity than the known results. Then rheological, DLS, and TEM studies have revealed the intriguing self-assembly behavior of the novel gemini surfactants. This study has proved the effectiveness of the design of gemini alkyl glucosides which is modular, extendable, and synthetically simple. The new gemini surfactants have great potential as nano carriers in drug and gene delivery.