9-L-Hydroxy-octadecansaeuremethylester | 23559-94-6

• 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: 9-L-Hydroxy-octadecansaeuremethylester
• 英文别名: methyl (9S)-9-hydroxyoctadecanoate
• CAS: 23559-94-6
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: QDFNTRIETZJNIC-SFHVURJKSA-N

物化性质

• 沸点：
  399.7±25.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-L-Hydroxy-octadecansaeuremethylester 在 吡啶 、 chromium(VI) oxide 、 硼氘化锂 、 硫酸 、 三氟化硼 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 methyl (9R)-[9-2H]-stearate
  参考文献：
  名称：

  Exploring the Hydroxylation−Dehydrogenation Connection:  Novel Catalytic Activity of Castor Stearoyl-ACP Δ⁹ Desaturase

  摘要：

  The novel product profile obtained by incubating chiral fluorinated substrate analogues with castor stearoyl-ACP Delta(9) desaturase has been rationalized through a series of labeling studies. It was found that the introduction of the Z-double bond between C-9 and C-10 of the parent substrate occurs with pro-R enantioselectivity-a result that accounts for the observed stereochemistry of oxidation products derived from (9R)- and (9S)-9-fluorostearoyl-ACP. Oxidation of (9R)-9-fluorostearoyl-ACP occurs via at least two rapidly interchanging substrate conformations in the active site as detected by reaction pathway branching induced by deuteration at C-10 and C-11. Hydroxylation and desaturation of this substrate share the same site of initial oxidative attack.

  DOI：

  10.1021/ja012252l
• 作为产物：
  描述：

  9-Hode 在 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 2.5h， 生成 9-L-Hydroxy-octadecansaeuremethylester
  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

• Oxygenated fatty acids of isano oil
  作者：Roger W. Miller、David Weisleder、Robert Kleiman、Ronald D. Plattner、Cecil R. Smith

  DOI：10.1016/s0031-9422(00)86701-1

  日期：1977.1

  Abstract Four new oxygenated acetylenic acid—8-oxo-octadeca-9,11-diynoic ( 1a ), 8-hydroxyoctadeca-10,12-diynoic ( 3a ), 8-oxo-octadeca-9,11-diyn-17-enoic

  摘要 四种新型含氧炔酸——8-oxo-octadeca-9,11-diynoic ( 1a ), 8-hydroxyoctadeca-10,12-diynoic ( 3a ), 8-oxo-octadeca-9,11-diyn-17-enoic
• Three Novel Polyacetylene Triglycendes, Lycogarides A-C, from the Myxomycetes Lycogala epidendrum.
  作者：Toshihiro HASHIMOTO、Kyoko AKAZAWA、Motoo TORI、Yukiko KAN、Takenori KUSUMI、Haruko TAKAHASHI、Yoshinori ASAKAWA

  DOI：10.1248/cpb.42.1531

  日期：——

  Three novel polyacetylene triglycerides, named lycogarides A-C (1-3), have been isolated from the Myxomycetes Lycogala epidendrum. Their relative structures have been established by a combination of two-dimension NMR spectroscopy and chemical degradation. The absolute structures of compounds 1 and 2 were deduced from the modified Mosher's and dibenzoate exiton chirality methods of their derivatives.

  从粘液菌Lycogala epidendrum中分离出三种新型聚乙炔甘油三酯，命名为lycogarides A-C（1-3）。通过二维核磁共振谱和化学降解的方法确定了它们的相对结构。化合物1和2的绝对结构是通过修正的Mosher法和二苯甲酸盐出口手性的方法推导出来的。
• Absolute configurations of 13-hydroxydocosanoic and 17-hydroxyoctadecanoic acids
  作者：A. P. Tulloch

  DOI：10.1139/v68-616

  日期：1968.12.1

  Methyl 13-D- and 13-L-hydroxydocosanoates have been synthesized from 9-D- and 9-L-hydroxy-octadecanoic acids. Comparison of these esters with the methyl ester of 13-hydroxydocosanoic acid, produced by Candida bogoriensis, shows that the natural product has the L-configuration. The known 2-D-octadecanol has been prepared from 17-hydroxyoctadecanoic acid, produced by Torulopsis apicola, showing that this acid also has the L-configuration. Most naturally occurring long-chain hydroxy acids, however, have the D-configuration.

  13-D-和13-L-羟基二十二酸甲酯已从9-D-和9-L-羟基十八烷酸合成。将这些酯与由波尔多曲霉产生的13-羟基二十二酸甲酯进行比较，结果显示天然产物具有L-构型。已从由顶芽酵母产生的17-羟基十八烷酸制备了已知的2-D-辛醇，表明该酸也具有L-构型。然而，大多数天然存在的长链羟基酸具有D-构型。
• Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation
  作者：Cynthia Ebert、Fulvia Felluga、Cristina Forzato、Marco Foscato、Lucia Gardossi、Patrizia Nitti、Giuliana Pitacco、Carla Boga、Paolo Caruana、Gabriele Micheletti、Natalia Calonghi、Lanfranco Masotti

  DOI：10.1016/j.molcatb.2012.06.017

  日期：2012.11

  Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas' rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned. (C) 2012 Elsevier B.V. All rights reserved.
• Exploring the Hydroxylation−Dehydrogenation Connection:  Novel Catalytic Activity of Castor Stearoyl-ACP Δ⁹ Desaturase
  作者：Behnaz Behrouzian、Christopher K. Savile、Brian Dawson、Peter H. Buist、John Shanklin

  DOI：10.1021/ja012252l

  日期：2002.4.1

  The novel product profile obtained by incubating chiral fluorinated substrate analogues with castor stearoyl-ACP Delta(9) desaturase has been rationalized through a series of labeling studies. It was found that the introduction of the Z-double bond between C-9 and C-10 of the parent substrate occurs with pro-R enantioselectivity-a result that accounts for the observed stereochemistry of oxidation products derived from (9R)- and (9S)-9-fluorostearoyl-ACP. Oxidation of (9R)-9-fluorostearoyl-ACP occurs via at least two rapidly interchanging substrate conformations in the active site as detected by reaction pathway branching induced by deuteration at C-10 and C-11. Hydroxylation and desaturation of this substrate share the same site of initial oxidative attack.