1-O-十二烷基-rac-甘油 | 1561-07-5

• 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-O-十二烷基-rac-甘油
• 英文名称: 3-dodecyloxypropane-1,2-diol
• 英文别名: 1-dodecyl glycerol ether；rac-1-O-dodecylglycerol；3-(dodecyloxy)-1,2-propanediol；3-dodecoxypropane-1,2-diol
• CAS: 1561-07-5
• 化学式: C₁₅H₃₂O₃
• 分子量: 260.417
• InChiKey: GBXRUYNQDDTQQS-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  390.5±22.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• WGK Germany：
  3
• 储存条件：
  密封储存于阴凉、干燥的库房中。冷藏时温度应保持在-20°C。

制备方法与用途

十二烷基-赖氨酸-甘油是一种生物化学试剂，可用作生物材料或有机化合物，广泛应用于生命科学相关研究。

反应信息

• 作为反应物：
  描述：

  1-O-十二烷基-rac-甘油 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.0h， 生成 [1-[Tert-butyl(dimethyl)silyl]oxy-3-dodecoxypropan-2-yl] hexadecanoate
  参考文献：
  名称：

  Nucleoside Conjugates. 14. Synthesis and Antitumor Activity of 1-.beta.-D-Arabinofuranosylcytosine Conjugates of Ether Lipids with Improved Water Solubility

  摘要：

  A series of ara-CDP-rac-1-O-alkyl-2-O-acylglycerol (9a-f), analogues of highly active ara-CDP-rac-1-O-hexadecyl-2-O-palmitoylglycerol (1) and Cytoros(2) (2), was prepared, and solubility, lipophilicity, and structure-activity relationships of these conjugates were investigated. Conjugates 9a-f containing sn-1 alkyl (C-16) and the sn-2 fatty acyl (>C-16) such as conjugate 1 were sparingly soluble. Conjugates 9a-c,e were almost completely solubilized in water by shaking. However, a large portion of conjugates 9d and 9f in water by shaking exist in micelles with mean diameters ranging 7.0-55.2 nm. The partition coefficients (1-octanol/PBS) of the water-soluble conjugates were about 9-18 times greater than that of ara-C. A single dose (300 mg/kg) of conjugates 9d and 9f produced a significant increase in life span (ILS 206 to >543%) with 17-67% long-term survivors (>45 days) in mice bearing ip-implanted L1210 lymphoid leukemia. These results were comparable to those of the previous conjugate 1 and Cytoros (2). In contrast, conjugates 9a-c,e at single doses were less effective (ILS 69-178% with no long-term survivors). However, two (qd, 1, 7) or three (qd 1, 5, 9) divided doses of these conjugates were found to be as effective as a single dose of the previous conjugates. The three divided doses (150 mg/kg per day) of conjugates 9d, 9e, and 9f produced a remarkable antitumor activity in L1210 leukemic mice (ILS >350% with >50% long-term survivors). Because of the convenient formulation and the significant antitumor activities, the water-soluble conjugates 9d, 9e, and 9f warrant further investigation.

  DOI：

  10.1021/jm00010a006
• 作为产物：
  描述：

  溴代十二烷 在 盐酸 、 sodium hydride 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 2.0h， 生成 1-O-十二烷基-rac-甘油
  参考文献：
  名称：

  嵌合厄洛替尼-烷基磷脂杂种的设计，合成和细胞毒性。

  摘要：

  制备了两个系列的厄洛替尼-烷基磷脂杂种，并使用厄洛替尼和米替福辛作为参考标准，评估了它们对代表肺癌，乳腺癌，肝癌和皮肤癌的四种细胞系的抗增殖活性。酰胺类似物比类似酯引起的细胞毒性活性更高。酰胺衍生物8d和8e表现出有希望的广谱抗增殖活性，并且比参考厄洛替尼和米替福辛具有更高的疗效。对于8e和8d，它们的细胞GI50值分别在24.7-46.9μM和26.8-43.1μM的范围内。与统计相关分析相结合，制得的化合物对EGFR激酶反应和Akt磷酸化的抑制活性的测定结果表明，其他机制可能有助于其引起的细胞毒性。此外，统计相关分析表明，酰胺系列引发细胞毒性的机制可能与酯系列不同。另外，相关分析表明，根据细胞系类型的不同，机制也有所不同。

  DOI：

  10.1016/j.bioorg.2018.11.021

文献信息

• 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: catalytic reductive alkylation and transesterification/reduction
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1039/c3gc36907b

  日期：——

  esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters

  从可用的和生物来源的甲酯中， 甘油单酸酯或油酸向日葵精制油，通过两种不同途径以高收率和选择性获得了相应的1- O-烷基（二）甘油醚。对于甲酯，在1mol％的Pd / C和酸助催化剂的存在下，在50巴的氢气压力下，实现了与（二）甘油的还原性烷基化。从甲酯或三油精 包括第一次酯交换反应成相应的 甘油单酸酯与BaO / Al 2 O 3 催化剂，然后 减少在H 2压力下，用可循环利用的非均相催化体系Pd / C和Amberlyst 35合成所需的甘油单醚。另外，还提出了反应机理。
• METHOD FOR PREPARING GLYCEROL ETHER AND GLYCOL ETHER
  申请人：RHODIA OPERATIONS

  公开号：US20150080613A1

  公开（公告）日：2015-03-19

  The present invention concerns a method for preparing glycerol ether or glycol ether comprising the reaction of a compound of formula (II) with a compound of formula (III) in the presence of a heterogeneous acid catalyst of formulas (II) and (III).

  本发明涉及一种制备甘油醚或乙二醇醚的方法，包括在异相酸催化剂的存在下，将式（II）化合物与式（III）化合物反应。
• Method of treating hepatitis virus infections
  申请人：Wake Forest University

  公开号：US05770584A1

  公开（公告）日：1998-06-23

  A method of treating hepatitis virus infection is disclosed. The method comprising administering to a human subject in need of such treatment an effective hepatitis virus-combatting amount of an alkyl lipid or alkyl lipid derivative.

  揭示了一种治疗肝炎病毒感染的方法。该方法包括向需要此类治疗的人类主体施用一种有效的抗肝炎病毒量的烷基脂质或烷基脂质衍生物。
• Selective Synthesis of 1-<i>O</i>-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1002/cssc.201200447

  日期：2012.12

  (Poly)glycerol monoethers were synthesized in good yield and selectivity by the catalytic reductive alkylation of glycerol, diglycerol, and triglycerol with readily available, cheap and/or bio‐sourced carboxylic acids. The reaction was catalyzed by 1 mol % of Pd/C under 50 bar H2 using an acid ion‐exchange resin as a recyclable cocatalyst. The catalytic system was recycled several times, and a mechanism

  （聚）甘油单醚是通过甘油，二甘油和三甘油与现成的廉价和/或生物来源的羧酸的催化还原烷基化反应而合成的，具有良好的收率和选择性。使用酸性离子交换树脂作为可循环助催化剂，在50 bar H 2下以1 mol％的Pd / C催化反应。催化系统被回收了几次，并提出了这种转化的机理。
• Glycerin derivatives and process for producing the same
  申请人：KAO CORPORATION

  公开号：EP0624563A1

  公开（公告）日：1994-11-17

  Glycerine derivatives represented by formula (1A), (2A) and (3A): wherein R1a, R2a, R1b, R2b, R1c, and R2c are as defined in the disclosure, and process for producing glycerin derivatives, including the glycerin derivatives (1A), (2A) and (3A), are disclosed. The glycerin derivatives have satisfactory physical properties and are applicable as lubricants or polar oils and also have mutual effects with water and are applicable as emulsifying agents or moisture retaining agents. The process makes it possible to synthesize glycerin derivatives from easily and economically available aldehydes or ketones in high yields.

  公式（1A）、（2A）和（3A）代表的甘油衍生物：其中R1a、R2a、R1b、R2b、R1c和R2c如披露中所定义，并公开了生产甘油衍生物的方法，包括甘油衍生物（1A）、（2A）和（3A）。这些甘油衍生物具有令人满意的物理性质，可用作润滑剂或极性油，并且与水有相互作用，可用作乳化剂或保湿剂。该方法使得可以从易于获得且经济可行的醛类或酮类高产率地合成甘油衍生物。

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