methyl 9-methoxyoctadecanoate | 29647-23-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 9-methoxyoctadecanoate
• 英文别名: Methyl-9-methoxy-stearate
• CAS: 29647-23-2
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: PBGIQXFYPBIGEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-Hode 在 吡啶 、 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、275.8 kPa 条件下， 反应 98.5h， 生成 methyl 9-methoxyoctadecanoate
  参考文献：
  名称：

  9-羟基硬脂酸衍生物的合成及其对 HT 29 癌细胞的抗增殖活性

  摘要：

  9-羟基硬脂酸 (9-HSA) 是一种内源性细胞脂质，对癌细胞具有抗增殖和选择性作用。为了研究第 9 位取代基和甲基酯官能度对生物活性的影响，合成了一系列衍生物。9-羟基硬脂酸甲酯和9-氨基硬脂酸甲酯的两种不同的对映异构体对HT29细胞系显示出抗增殖活性。这表明第 9 位基团能够与分子靶标形成氢键的重要性。此外，当 9-HSA 的羧基被酯化时，必须保持这种效果。生物试验表明，与甲酯相反，胺会导致细胞毒性。

  DOI：

  10.3390/molecules24203714

文献信息

• Application of metal triflate catalysts for the trans-esterification of Jatropha curcas L. oil with methanol and higher alcohols
  作者：Louis Daniel、Carolus B. Rasrendra、Arjan Kloekhorst、Antonius A. Broekhuis、Robert Manurung、Hero J. Heeres

  DOI：10.1007/s11746-013-2364-3

  日期：2014.2

  This paper describes an experimental study on the application of metal triflate salts for the (trans‐) esterification of fatty esters (triolein, methyl oleate, methyl linoleate), fatty acid (oleic acid), as well as Jatropha curcas L. oil with methanol and higher alcohols (ethanol, n‐propanol, iso‐propanol, iso‐butanol, tert‐butanol). The effect of the metal type (scandium, bismuth, aluminium, lanthanum

  本文描述了金属三氟甲磺酸盐在脂肪酯（三油精，油酸甲酯，亚油酸甲酯），脂肪酸（油酸）以及麻风树油与甲醇的（反式）酯化中的应用的实验研究。以及高级醇（乙醇，正丙醇，异丙醇，异丁醇，叔丁醇）。评估了金属类型（scan，铋，铝，镧，铜，锌）和工艺条件对反应性能的影响。使用Al（OTf）3获得最高的转化率。三油精与甲醇的反应在165°C下进行1小时的转化率为99 mol％，主要产物为甲酯。此外，尽管在混合物中的分数小于20摩尔％，但观察到脂肪酸链中碳-碳双键的部分甲氧基化。所述反式-esterification反应还成功地使用高级醇，得到> 95％的转化为乙醇进行，Ñ丙醇，异丙醇和异丁醇，而叔丁醇不具有反应性。对于油酸与甲醇的反应，观察到定量酯化，碳-碳双键的部分甲氧基化以及少量内酯的形成。使用的Al的方法（OTF）3被成功所执行的反式JO的-esterification反应（2.1重量％的FFA含
• Novel liquid fatty acid derivatives
  申请人：NEW JAPAN CHEMICAL CO.,LTD.

  公开号：EP0713855A1

  公开（公告）日：1996-05-29

  A fatty acid derivative of formula (1) wherein each of X, Y and Z, which are the same or different, is a C₁-C₁₀ alkyloxy group or a C₃-C₁₀ cycloalkyloxy group, at least one of X, Y and Z being a C₁-C₁₀ alkyloxy group or a C₃-C₁₀ cycloalkyloxy group, each of a, b, c and d, which are the same or different, is an integer of 0 to 17 and the value of a + b + c + d is from 13 to 17; and salts thereof.

  式（1）的脂肪酸衍生物，其中X、Y和Z分别为C₁-C₁₀烷氧基或C₃-C₁₀环烷氧基，可以相同也可以不同，X、Y和Z中至少有一个为C₁-C₁₀烷氧基或C₃-C₁₀环烷氧基，a、b、c和d分别为0到17的整数，且a + b + c + d的值为13到17；以及其盐。
• Neighboring methoxyl participation in the acid catalyzed methoxylation of methylene-interrupted fatty acids
  作者：Néstor M. Carballeira、Marı́a V. González、Mayra Pagán

  DOI：10.1016/s0009-3084(97)00062-5

  日期：1997.10

  The boron trifluoride-methanol derivatization of methyl 9,12-octadecadienoate was studied. This methylene-interrupted diene was reacted with 50% BF3-MeOH for 15 h at 0-5 degrees C and the four monomethoxy and two dimethoxy derivatives thus obtained were analyzed by gas chromatography-mass spectrometry. The only dimethoxy adducts observed were characterized as methyl 9,12-dimethoxyoctadecanoate and methyl 10,13-dimethoxyoctadecanoate. The complete regiospecificity observed in the formation of the dimethoxy adducts is best explained by a common O-methyltetrahydrofuranium ion as the only intermediate under these reaction conditions. (C) 1997 Elsevier Science Ireland Ltd.
• Ansari,F.H. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 1053 - 1054
  作者：Ansari,F.H. et al.

  DOI：——

  日期：——
• Methoxylation of methyl oleate in the presence of dealuminated Y faujasites in their protonic form
  作者：Clément Lansalot-Matras、Paul Lozano、Daniel Pioch、Annie Finiels、Claude Moreau、Sylvain Claude

  DOI：10.1007/s11746-006-5030-1

  日期：2006.8

  AbstractMethoxylation of methyl oleate into methyl methoxy stearate was carried out in a batch reactor at temperatures ranging from 150 to 190°C in the presence of dealuminated H‐Y faujasites as catalysts. In the presence of an excess of methanol, the H‐Y faujasite with a Si/Al ratio of 15 was shown to achieve the title reaction with a yield of methyl methoxy stearate that does not exceed 40% because of the parallel formation, at comparable rates, of methyl oleate isomers identified as methyl elaidate, methyl trans‐vaccenate, and methyl cis‐vaccenate. Isomerization reactions were confirmed to occur rapidly in an independent manner. FFA are also present in small amounts owing to the in situ dehydration of methanol and subsequent hydrolysis of the esters. Finally, starting from pure oleic acid leads to results similar to those obtained with methyl oleate as the starting material.