(Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester | 84799-82-6

• 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: (Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester
• 英文别名: methyl (S)-ricinoleate；methyl ricinoleate；Ricinolsaeure-methylester；methyl (Z,12S)-12-hydroxyoctadec-9-enoate
• CAS: 84799-82-6
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: XKGDWZQXVZSXAO-GFBZKKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  (Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester 在 甲醇 、 potassium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以1.98 g的产率得到(Z)-(S)-12-hydroxyoctadec-9-enoic acid
  参考文献：
  名称：

  Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid

  摘要：

  (R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.06.005
• 作为产物：
  描述：

  (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester 在 甲醇 、 sodium methylate 作用下， 反应 50.5h， 生成 (Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid

  摘要：

  (R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2014.06.005

文献信息

• Antimicrobial Potential of Chiral Amide Derivatives of Ricinoleic and 3‐Hydroxynonanoic Acid
  作者：Sylwia Matysiak、Julia Zabielska、Józef Kula、Alina Kunicka‐Styczyńska

  DOI：10.1002/aocs.12292

  日期：2020.1

  obtained compounds showed antimold potential; however, the tested species of molds were more susceptible to derivatives of 3‐hydroxynonanoic acid than to amides obtained from ricinoleic acid (RA). Interestingly, hydroxamic acids derived from RA exhibited the best activity against Candida albicans and Candida tropicalis. On the other hand, hydroxamic acids derived from 3‐hydroxynonanoic acid showed the

  最近已经观察到脂肪酸酰胺在药物化学中的作用越来越大。因此，使用简单快速的方法，可以得到一系列蓖麻油酸和3-羟基壬酸的手性酰胺衍生物（24种化合物），产率为31–95％。然后，评估了它们对代表革兰氏阳性和革兰氏阴性细菌，酵母菌和霉菌的13种微生物的抗菌活性。所获得的化合物显示出抗霉变的潜力。但是，测试过的霉菌种类对3-羟基壬酸衍生物的敏感性要高于从蓖麻油酸（RA）获得的酰胺。有趣的是，源自RA的异羟肟酸对白色念珠菌和热带念珠菌表现出最好的活性。。另一方面，衍生自3-羟基壬酸的异羟肟酸对其余测试微生物，尤其是对雪松假单胞菌具有最佳的抗菌潜力。所获得的衍生物可以被认为是具有潜在药理学意义的化合物，由于日益增加的微生物抗性问题，这是重要的。
• Chiral amide derivatives of ricinoleic acid and 3-hydroxynonanoic acid synthesis and cytotoxic activity
  作者：Sylwia Matysiak、Józef Kula、Alina Błaszczyk

  DOI：10.1007/s00044-019-02348-y

  日期：2019.7

  series of chiral ricinoleic and 3-hydroxynonanoic acid derivatives were synthesized in this study using various chemical and biochemical procedures. An effective method for preparation of methyl esters of 3-hydroxynonanoic acid from castor oil or methyl ricinoleate by ozonolysis and oxidation was developed. Simple, fast, and efficient procedures were applied to obtain different primary and secondary

  在这项研究中，使用各种化学和生化方法合成了一系列手性蓖麻油酸和3-羟基壬酸衍生物。提出了一种通过臭氧分解和氧化从蓖麻油或蓖麻油酸酯中制备3-羟基壬酸甲酯的有效方法。应用简单，快速和有效的程序来获得不同的伯和仲，环状和无环酰胺，包括异羟肟酸。在蓖麻油酸和3-羟基壬酸的24种合成衍生物（即甲酯，酰胺和异羟肟酸）中，首次获得并描述了16种化合物。合成的化合物对被测癌细胞具有活性，但对3-羟基壬酸衍生的异羟肟酸具有最佳的细胞毒性作用（11）对抗HeLa细胞。通常，大多数测试化合物对HT29的毒性都比HeLa癌细胞高。结果还表明，特定衍生物的（R）-和（S）-对映体的活性之间没有显着差异。
• Synthesis of (<i>R</i>)- and (<i>S</i>)-Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity
  作者：Sylwia Matysiak、Julia Zabielska、Józef Kula、Alina Kunicka-Styczyńska

  DOI：10.1002/aocs.12013

  日期：2018.1

  fatty acid amides derived from (R)‐ and (S)‐ricinoleic acid and 4 cyclic and acyclic amines were synthesized in a proecological solvent‐free process with yields ranging from 43 to 88%. All S‐configured compounds and both enantiomers of amide with 2‐amino‐2‐methyl‐1‐propanol were obtained and studied in terms of biological activity for the first time. The evaluation of antimicrobial activity of (R)‐ and

  在无保护性溶剂的过程中合成了一系列衍生自（R）和（S）蓖麻油酸的脂肪酸酰胺和4个环胺和无环胺，收率范围为43％至88％。首次获得了所有S构型的化合物以及酰胺与2-氨基-2-甲基-1-丙醇的两种对映异构体，并首次就生物学活性进行了研究。（R）和（S）-蓖麻油酸衍生物对代表革兰氏阴性和革兰氏阳性细菌，酵母和霉菌的13种不同微生物的抗菌活性评估显示出对革兰氏阳性细菌特别是黄球菌和微球菌的显着抑制活性。枯草芽孢杆菌，并针对选定的霉菌。乙醇胺和吡咯烷衍生的酰胺显示出最有希望的抗菌和抗霉菌潜力。蓖麻油酸和吡咯烷的衍生物对选择的两种霉菌，巴西曲霉和扩张青霉的活性最高。而且，R-构型的类似物对枯草芽孢杆菌最有效。蓖麻油酸与乙醇胺的酰胺对金黄色葡萄球菌显示出显着的潜力，这使它们与该细菌具有很高抗性的其余测试衍生物区分开来。
• Synthesis and cytotoxicity of (<i>R</i>)- and (<i>S</i>)-ricinoleic acid amides and their acetates
  作者：Sylwia Matysiak、Agnieszka Chmiel、Janusz Skolimowski、Jozef Kula、Beata Pasternak、Alina Blaszczyk

  DOI：10.1002/chir.22733

  日期：2017.10

  An environment‐friendly, free of solvent, process for the synthesis of (R)‐ and (S)‐ricinoleic acid amides has been developed. Starting from methyl ricinoleates and pyrrolidine or ethanolamine, the corresponding amides were obtained with yields ranging from 83–88%. Among 12 synthesized derivatives of ricinoleic acid, including the starting methyl esters, amides, and their acetates, nine compounds were

  环保，无溶剂的合成（R）和（S的方法）-蓖麻油酰胺已被开发出来。从蓖麻油酸甲酯和吡咯烷或乙醇胺开始，可获得相应的酰胺，产率为83-88％。在12种合成的蓖麻油酸衍生物中，包括起始的甲基酯，酰胺及其乙酸酯，首次获得了9种化合物并进行了测试。对蓖麻油酸衍生物的细胞毒性研究表明，甲酯是最不具细胞毒性的化合物，其结构的改变导致所得产物对癌细胞和正常淋巴细胞的细胞毒性增加。乙醇胺衍生的酰胺的两种对映体均显示出最有希望的抗癌潜力。
• BoC₂O Mediated Macrolactonisation: Syntheses of R-(+)-Ricinoleic Acid Lactone and (±)-12-OH-Stearic Acid Lactone
  作者：M. Nagarajan

  DOI：10.1080/00397919908086253

  日期：1999.7

  An efficient chemoenzymatic synthesis of R-(+)-ricinoleic acid lactone and (+/-)-12-OH-stearic acid lactone using Boc(2)O mediated macrolactonisation is reported.

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