methyl ricinoleate | 41989-07-5

• 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 ricinoleate
• 英文别名: 12-hydroxy-cis-9-octadecenoic acid methyl ester；methyl-12-hydroxy-Z-9-octadecenoate；ricinol acid methylester；ricinoleic acid methyl ester；Ricinolsaeure-methylester；methyl riconoleate；methyl (Z)-12-hydroxyoctadec-9-enoate
• CAS: 41989-07-5
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: XKGDWZQXVZSXAO-RAXLEYEMSA-N

物化性质

• 沸点：
  412.0±28.0 °C(Predicted)
• 密度：
  0.926±0.06 g/cm3(Predicted)

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
• 安全说明：
  S,S10,S21,S8

反应信息

• 作为反应物：
  描述：

  methyl ricinoleate 在 镍 氢氧化钾 、 氢气 作用下， 生成 12-羟基硬脂酸
  参考文献：
  名称：

  强碱中的有机反应-III：酮酸和羟基酸的裂变

  摘要：

  用合适的脂肪酸衍生物进行的研究澄清了醇和酮在浓碱中的许多反应。

  DOI：

  10.1016/0040-4020(60)80033-6
• 作为产物：
  描述：

  蓖麻油酸 在 conjugated linoleic acid dehydrogenase 、 nicotinamide adenine dinucleotide 、 还原型辅酶Ⅰ 、 bovine serum albumin 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 methyl ricinoleate
  参考文献：
  名称：

  Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

  摘要：

  Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD(+)-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with alpha- or beta-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 mu M with a k(cat) of 7.6 x 10(-3) s(-1). The apparent K-m value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 mu M with a k(cat) of 5.7 x 10(-1) s(-1). In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.03.020

文献信息

• On the mechanism and synthetic applications of the thermal and alkaline degradation of c-18 castor oil
  作者：S. Ranganathan、Raaj Kumar、V. Maniktala

  DOI：10.1016/s0040-4020(01)99322-6

  日期：1984.1

  c-8 via unique sequence involving a primary reaction which is associated with three different types of redox systems as well as with uncoupled oxidation, the overall change amounting to a milieu of hydride transfer, π -migration, retro-Michael, retro-aldol, Meerwein-Pondorff-Verley as well as Cannizzaro type of reactions. These findings which constitute the core of the present work, are of significance

  由π蓖麻油片段的C-18骨架，热至C-11 + C-7 2 S +π 2 S +Ò 2s过程，并通过独特的顺序将热碱转化为c-10 + c-8，该过程涉及与三种不同类型的氧化还原系统以及未偶联的氧化有关的主要反应，总体变化相当于氢化物转移的环境π -迁移，迈克·怀特（Michael），怀特·阿尔多（Retro-aldol），Meerwein-Pondorff-Verley以及Cannizzaro型反应。这些发现构成了本研究的核心，不仅对于了解蓖麻油的两个最重要的反应具有重要意义，而且在利用这些知识来引导和优化所需产品方面也具有重要意义。此外，它们为机械有机化学增加了一个独特的方面。蓖麻油C-18→C-11 + C-7变化的协调性质的令人信服的证据是，将12-羟基十八烷基9-壬酸甲酯干净地转化为新型有用的烯丙基酯，十一碳烯酸9,10-讨人喜欢。对不同的α-取代的γδ-不饱和醇进行的模型研究表明，π2个S
• The synthesis of PGF1α by re-structuring of castor oil
  作者：D. Ranganathan、S. Ranganathan、M.M. Mehrotra

  DOI：10.1016/0040-4020(80)80089-5

  日期：1980.1

  oil has been transformed—via methyl ricinoleate—to PGF1α by strategy wherein 16 of the 18 carbons of the castor oil backbone are incorporated in the C-20 PGF1α, involving, inter alia, a novel procedure for the regiospecific functionalisation of terminal olefins, a novel degradation of aldehyde to lower acid and strategies useful for the generation of the highly functionalised prostanoid system, which

  蓖麻油已被改造-经由蓖麻油酸甲酯到PGF 1个α由策略，其中所述18个碳原子的蓖麻油骨架的16中的C-20 PGF并入1 α，涉及，除其他外，对于区域专一性官能一种新颖的过程末端烯烃的合成，醛向低级酸的新降解以及可用于生成高度官能化的类前列腺素系统的策略，这些方法特别说明了MEM保护基在多种化学转化中的效用。此外，此工作描述了具有潜在效用和新颖的均PGP的合成合成子的制备1 α。
• Pyridinium Dichromate in Organic Chemistry: A New Synthesis of Enedicarbonyl Compounds
  作者：Maurizio D'Auria、Antonella De Mico、Franco D'Onofrid、Arrigo Scettri

  DOI：10.1055/s-1985-31419

  日期：——

  Enedicarbonyl compounds (2-alkene-1,4-diones) are prepared by oxidation of 1-substituted 3-alkenols (homoallylic alcohols) with pyridinium dichromate in dimethylformamide. The reaction proceeds via 3-alkenyl ketones as intermediates which can in some cases be isolated after short reaction times.

  乙二酮化合物（2-烯-1,4-二酮）通过以吡啶二铬酸盐在二甲基甲酰胺中氧化1-取代的3-烯醇（同烯丙醇）来制备。该反应经过3-烯基酮作为中间体进行，在某些情况下，反应时间较短时可以分离得到这些中间体。
• Synthesis and biological evaluation of ricinoleic acid-based lipoamino acid derivatives
  作者：Y. Mohini、R.B.N. Prasad、M.S.L. Karuna、Y. Poornachandra、C. Ganesh Kumar

  DOI：10.1016/j.bmcl.2016.09.063

  日期：2016.11

  A series of novel ricinoleic acid based lipoamino acid derivatives were synthesized from (Z)-methyl-12-aminooctadec-9-enoate and different l-amino acids (glycine, alanine, phenyl alanine, valine, leucine, isoleucine, proline and tryptophan). The structures of all the prepared compounds were characterized by 1H NMR, 13C NMR and mass spectral studies. The title compounds were evaluated for their antimicrobial

  由（Z）-甲基-12-氨基十八烷基-9-烯酸酯和不同的1-氨基酸（甘氨酸，丙氨酸，苯基丙氨酸，缬氨酸，亮氨酸，异亮氨酸，脯氨酸和色氨酸）合成了一系列基于蓖麻油酸的脂氨基酸衍生物。。通过1 H NMR，13 C NMR和质谱研究表征所有制备的化合物的结构。评价标题化合物的抗微生物和抗生物膜活性。在所有衍生物中，化合物7a（Z）-甲基-12-（2-氨基乙酰胺基）octadec-9-烯酸酯显示出有希望的抗菌活性（MIC，3.9–7.8μg/ mL）和化合物7b（Z）-甲基12-（2-氨基丙酰胺基）octadec-9-烯酸酯和7g（Z）-甲基-12-（吡咯烷-2-甲酰胺基）octadec-9-烯酸酯具有中等活性（MIC，7.8–31.2μg/ mL）选择性地针对四种不同的革兰氏阳性细菌菌株，例如金黄色葡萄球菌MTCC 96，枯草芽孢杆菌MTCC 121，金黄色葡萄球菌MLS-16 MTCC 294
• Synthesis and desaturation of monofluorinated fatty acids 1
  作者：Peter H. Buist、Kostas A. Alexopoulos、Behnaz Behrouzian、Brian Dawson、Bruce Black

  DOI：10.1039/a701571b

  日期：——

  A series of monofluoro C16 and C18 fatty acids have been synthesized and used as mechanistic probes for fatty acid desaturation. Only fluoroolefinic products are obtained when these compounds are processed by an in vivo Saccharomyces cerevisiae ω9 desaturating system as determined by 1H-decoupled 19F NMR and GC–MS analysis. No evidence for fluorohydrin formation has been found when either methyl (R,S)-9- or 10-fluoropalmitate (stearate) 3a,b and 5a,b was incubated with the ω9 desaturase. On desaturation α- and β-fluorine substituent effects (kH/kF) of magnitude 6.2 and 2.4, respectively, have been measured by direct competition experiments between 3a and 3b and between methyl 16-fluoropalmitate 3c and 3b. These results do not support the involvement of discrete hydroxylated and carbocationic intermediates in fatty acid desaturation. Substantial apparent steric effects have been observed for monofluorostearoyl substrates 5c–f bearing a fluorine distal from the site of initial oxidation. In the case of (R,S)-methyl 12-fluorostearate 5f, we show that both enantiomers are desaturated at comparable rates.

  一系列单氟代的C16和C18脂肪酸已被合成并作为机制探针用于脂肪酸脱饱和的研究。当这些化合物经过体内酿酒酵母ω9脱饱和系统处理后，根据1H去耦19F核磁共振和气相色谱-质谱分析，仅得到了含氟烯烃的产物。无论是甲基（R,S）-9-还是10-氟代棕榈酸（硬脂酸）3a,b和5a,b与ω9脱饱和酶共孵育时，均未发现形成氟醇的迹象。在脱饱和过程中，通过3a与3b以及甲基16-氟代棕榈酸3c与3b之间的直接竞争实验，分别测得α-和β-氟代取代基效应（kH/kF）大小为6.2和2.4。这些结果不支持脂肪酸脱饱和过程中涉及离散的羟基化和碳正离子中间体。对于远离初始氧化位点的氟代硬脂酰基底物5c–f，观察到了显著的表观立体效应。就（R,S）-甲基12-氟代硬脂酸5f而言，我们证明了两种对映体以相近速率进行脱饱和。