甲基17-羟基硬脂酸酯 | 2380-14-5

• 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17-羟基硬脂酸酯
• 英文名称: methyl 17-hydroxystearate
• 英文别名: 17-hydroxy-octadecanoic acid methyl ester；17-Hydroxy-octadecansaeure-methylester；Methyl 17-hydroxyoctadecanoate
• CAS: 2380-14-5
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: ZHIMEDOBRMCAAO-UHFFFAOYSA-N

物化性质

• 保留指数：
  2448.2

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  甲基17-羟基硬脂酸酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 17-Hydroxystearic acid
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6
• 作为产物：
  描述：

  甲基15-溴十五烷酸酯 在 甲醇 、 硫酸 、 镍 、 potassium carbonate 、 2-戊酮 、 丙酮 、 sodium iodide 作用下， 150.0 ℃ 、14.71 MPa 条件下， 生成 甲基17-羟基硬脂酸酯
  参考文献：
  名称：

  Bergstroem et al., Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 1157,1160, 1169

  摘要：

  DOI：

文献信息

• Microbiological oxidation of long-chain aliphatic compounds. Part III. 1-Halogenoalkanes, 1-cyanohexadecane, and 1-alkoxyalkanes
  作者：D. F. Jones、R. Howe

  DOI：10.1039/j39680002816

  日期：——

  glucose, the yeast Torulopsis gropengiesseri effects the following transformations: (a) long-chain 1-halogenoalkanes to αω-alkanedioic acids; (b) 1-cyanohexadecane to the cyanohydrin derivative of 16-oxohexadecanoic acid; (c) long-chain 1-methoxyalkanes and 1-ethoxyalkanes to ω-hydroxyalkanoic acids; (d) long-chain 1-propoxyalkanes to ω- and ω-1-hydroxyalkoxyalkanoic acids. The transformation products

  在含有葡萄糖的培养基中，灰鹤菌酵母进行以下转化：（a）将长链1-卤代烷烃转变为αω-链烷二酸；（a）将长链1-卤代烷烃转化为αω-链烷二酸；（b）1-氰基十六烷为16-氧代十六烷酸的氰醇衍生物；（c）长链的1-甲氧基烷烃和1-乙氧基烷烃成ω-羟基链烷酸；（d）长链的1-丙氧基烷烃为ω-和ω-1-羟基烷氧基链烷酸。转化产物作为糖脂与培养基分离。提出了解释这些转化的代谢途径。
• Tandem Isomerization/Hydroformylation/Hydrogenation of Internal Alkenes to <i>n</i>-Alcohols Using Rh/Ru Dual- or Ternary-Catalyst Systems
  作者：Yamato Yuki、Kohei Takahashi、Yoshiyuki Tanaka、Kyoko Nozaki

  DOI：10.1021/ja407523j

  日期：2013.11.20

  A one-pot three-step reaction, isomerization/hydroformylation/hydrogenation of internal alkenes to n-alcohols, was accomplished by employing a Rh/Ru dual-catalyst system. By using a combination of Rh(acac)(CO)2/bisphosphite and Shvo's catalyst, (Z)-2-tridecene was converted to 1-tetradecanol in 83% yield with high normal/iso selectivity (n/i = 12). The method was applicable to other internal alkenes

  内烯烃异构化/加氢甲酰化/加氢生成正醇的一锅三步反应是通过使用Rh/Ru双催化剂体系完成的。通过使用 Rh(acac)(CO)2/二亚磷酸酯和 Shvo 催化剂的组合，(Z)-2-十三烯以 83% 的产率转化为 1-十四醇，具有高正/异选择性 (n/i = 12)。该方法适用于其他内部烯烃，包括功能化烯烃，如烯醇和烯酸酯。此外，第三种组分 Ru3(CO)12 的加入有效地提高了油酸甲酯串联异构化/加氢甲酰化/氢化中的 n/i 比（从 n/i = 1.9 到 4.4）。对照实验表明异构化是由 Rh 和 Ru 介导的，并且 Rh 和 Ru 的共存对于 H2/CO 下醛的加氢是必不可少的。
• Microbiological oxidation of long-chain aliphatic compounds. Part V. Mechanism of hydroxylation
  作者：D. F. Jones

  DOI：10.1039/j39680002827

  日期：——

  [(17D)-17-3H1]stearate, and methyl [(17DL)-17-3H1]stearate have been prepared. Each of these compounds, mixed with methyl [U-14C]stearate, has been incubated with Torulopsis gropengiesseri, to give, after work-up, methyl 17-L-hydroxystearate and dimethyl octadecane-1,18-dioate. Determination of the 3H : 14C ratios of the latter compounds has established (a) that ω-hydroxylation and ω-1-hydroxylation of stearic acid

  甲基[（17大号）-17- 3 ħ 1 ]硬脂酸酯，甲基[（17 d）-17- 3 ħ 1 ]硬脂酸酯，以及甲基[（17 DL）-17- 3 ħ 1 ]硬脂酸已经制备。这些化合物中的每一种都与[U- 14 C]硬脂酸甲酯混合，已与Torulopsis gropengiesseri孵育，在后处理后得到17- L-羟基硬脂酸甲酯和十八烷基二甲基-1,18-二酸酯。3 H：14的测定后一种化合物的C比值已确定（a）硬脂酸的ω-羟基化和ω-1-羟基化是独立的反应，涉及氢原子总体上被羟基直接取代，（b）ω-硬脂酸的1-羟基化是立体有择方法，该方法发生与配置的保持力，以及（c）一个动力学同位素效应[（17的羟基化过程中可能操作大号）-17- 3 ħ 1 ]硬脂酸。1-溴的混合物[（16 DL）-16- 3 ħ 1 ]十七烷和1-溴[U- 14 C]十七烷被氧化以T. gropengiesseri后处理后得到1
• Engineering a Highly Regioselective Fungal Peroxygenase for the Synthesis of Hydroxy Fatty Acids
  作者：Patricia Gomez de Santos、Alejandro González‐Benjumea、Angela Fernandez‐Garcia、Carmen Aranda、Yinqi Wu、Andrada But、Patricia Molina‐Espeja、Diana M. Maté、David Gonzalez‐Perez、Wuyuan Zhang、Jan Kiebist、Katrin Scheibner、Martin Hofrichter、Katarzyna Świderek、Vicent Moliner、Julia Sanz‐Aparicio、Frank Hollmann、Ana Gutiérrez、Miguel Alcalde

  DOI：10.1002/anie.202217372

  日期：2023.2.20

  The biocatalytic hydroxylation of fatty acids is an appealing reaction, but the generation of over-oxidation by-products and the lack of selectivity hampers its transfer to industry. Now a highly selective and efficient peroxygenase has been engineered for the production of hydroxy fatty acids through a synthetic procedure that can be rapidly adapted to the preparative scale.

  脂肪酸的生物催化羟基化是一个吸引人的反应，但过度氧化副产物的产生和选择性的缺乏阻碍了它向工业的转移。现在，一种高选择性和高效的过氧化酶已被设计用于通过可快速适应制备规模的合成程序来生产羟基脂肪酸。
• Clickable Lipids: Azido and Alkynyl Fatty Acids and Triacylglycerols
  作者：Jonathan A. Zerkowski、Alberto Nuñez、Gary D. Strahan、Daniel K. Y. Solaiman

  DOI：10.1007/s11746-009-1442-z

  日期：2009.11

  AbstractHydroxy fatty acids (FAs), which were isolated from glycolipids that can be prepared fermentatively from fats and oils, have been synthetically modified to contain azide and alkyne functional groups. These particular functional groups were chosen because they can participate in a copper‐catalyzed reaction that combines them to form a 1,4‐triazole, known as a “click” reaction, which has been widely used in a variety of fields but remains underutilized in FA chemistry. Depending on the starting hydroxy FA, these groups can be close to the carboxy unit (using 3‐hydroxydecanoate) and hence the polar glycerol group, or distant from it (using 17‐hydroxyoctadecanoate). These structural alternatives will impart different properties to the triacylglycerols that are subsequently prepared from the modified FA. Finally, the click reaction was used to conjugate triacylglycerols to each other and to other molecules such as a glycolipid or a protected amine.