(E)-methyl 12-hydroxy-9-octadecenoate | 67529-83-3

• 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: (E)-methyl 12-hydroxy-9-octadecenoate
• 英文别名: Methyl (E)-12-hydroxyoctadec-9-enoate；ricinelaidic acid methyl ester；trans methyl ricinelaidate；methyl ricinoleate；Methyl-12-hydroxyoctadec-9-trans-enoat；Methyl-ricinelaidate；12-Hydroxy-9-octadecenoic acid methyl ester
• CAS: 67529-83-3
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: XKGDWZQXVZSXAO-JLHYYAGUSA-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

反应信息

• 作为反应物：
  描述：

  (E)-methyl 12-hydroxy-9-octadecenoate 在 palladium on activated charcoal 吡啶 、 氢气 、 氧气 、 亚甲兰 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 四氯化碳 、 甲苯 为溶剂， 反应 25.5h， 生成 硬酯酸甲酯C18
  参考文献：
  名称：

  Bascetta, Emanuele; Gunstone, Frank D.; Scrimgeour, Charles M. S., Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2199 - 2206

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl ricinoleate 在 二苯二硫醚 作用下， 以 环己烷 为溶剂， 反应 10.0h， 以83%的产率得到(E)-methyl 12-hydroxy-9-octadecenoate
  参考文献：
  名称：

  Synthesis of methyl 9,12‐epoxyoctadecanoate from castor oil

  摘要：

  摘要 我们在此报告 9,12-环氧十八烯酸甲酯（2-[7-甲氧羰基-庚基]-5-己基四氢呋喃）的合成。从蓖麻油甲酯中分离出的蓖麻油酸甲酯（12-羟基-9-顺式-十八烯酸甲酯）在紫外线辐射下以二苯基二硫化物作为自由基引发剂进行异构化，得到反式异构体蓖麻油酸甲酯。在二氯甲烷中缓慢加入 10%的溴溶液使后者环化，得到 10-溴-9,12-环辛基癸酸甲酯，在 Pd/C 催化剂作用下进行氢化，得到标题化合物--9,12-环辛基癸酸甲酯。

  DOI：

  10.1007/bf02540670

文献信息

• 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。
• Process for the synthesis of unsaturated alcohols
  申请人：Maughon R. Bob

  公开号：US20050080301A1

  公开（公告）日：2005-04-14

  A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

  一种制备不饱和醇（烯醇）的过程，例如，保护羟基取代的不饱和脂肪酸或脂肪酸酯，例如来自种子油的甲基蓖麻油酸甲酯，形成羟基保护的不饱和脂肪酸或脂肪酸酯; 同型交换或交叉交换羟基保护的不饱和脂肪酸或脂肪酸酯，以产生含有羟基保护的不饱和交换产物的产物混合物; 并在足以制备不饱和醇的条件下去除羟基保护的不饱和交换产物。优选地，通过交叉或同型交换将甲基蓖麻油酸甲酯转化为同型烯丙基单醇1-癸烯-4-醇或同型烯丙基多醇9-十八烯-7,12-二醇。
• Attempted synthesis of (9Z)-methyl 12-hydroperoxyoctadec-9-enoate
  作者：Emanuele Bascetta、Frank D. Gunstone

  DOI：10.1039/p19840002217

  日期：——

  The silver trifluoroacetate-assisted reaction of alkyl halides with hydrogen peroxide has been investigated. Methyl 12-bromostearate furnished, for the first time, methyl 12-hydroperoxystearate in 34% yield. Methyl 12-bromo-oleate, however, gave cyclopropane hydroperoxides (via a homoallylic cation rearrangement) and hydroperoxy epidioxides (presumably via methyl 12-hydroperoxyoleate which could not

  已经研究了三氟乙酸银与卤代烷与过氧化氢的辅助反应。12-溴硬脂酸甲酯首次以12％的产率提供了12-氢过氧硬脂酸甲酯。然而，12-溴-油酸甲酯产生了环丙烷氢过氧化物（通过均等阳离子重排）和氢过氧环氧乙烷（大概是通过12-氢过氧油酸甲酯无法分离）。在三氟乙酸银的存在下，通过使12-溴油酸甲酯与氢过氧化叔丁基反应，制得9，叔丁基过氧-10，11-亚甲基庚二酸甲酯。当三氟乙酸银被乙酸盐代替时，这些转化都没有发生。
• Yamada, Hiroshi; Ohsawa, Shoko; Sugai, Takeshi, Chemistry Letters, 1989, p. 1775 - 1776
  作者：Yamada, Hiroshi、Ohsawa, Shoko、Sugai, Takeshi、Ohta, Hiromichi、Yoshikawa, Sadao

  DOI：——

  日期：——
• Ahmad, Ishtiaque; Kathuria, Poonam; Singh, Sukhprit, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 8, p. 760 - 762
  作者：Ahmad, Ishtiaque、Kathuria, Poonam、Singh, Sukhprit

  DOI：——

  日期：——