methyl (R)-9-hydroxystearate | 6114-37-0

• 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 (R)-9-hydroxystearate
• 英文别名: 9-D-Hydroxy-octadecansaeuremethylester；Methyl 9(r)-hydroxyoctadecanoate；methyl (9R)-9-hydroxyoctadecanoate
• CAS: 6114-37-0
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: QDFNTRIETZJNIC-GOSISDBHSA-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)：
  6.6
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  methyl (R)-9-hydroxystearate 在 吡啶 、 chromium(VI) oxide 、 硼氘化锂 、 硫酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 5.0h， 生成
  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 methyl (R)-9-hydroxystearate
  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

• Divinylcarbinol Desymmetrization Strategy: A Concise and Reliable Approach to Chiral Hydroxylated Fatty Acid Derivatives
  作者：Kenji Sugimoto、Ami Kobayashi、Aki Kohyama、Haruka Sakai、Yuji Matsuya

  DOI：10.1021/acs.joc.0c02821

  日期：2021.3.5

  By the aid of the catalytic desymmetrization of divinylcarbinol as one-pot asymmetric induction and protection of olefin, asymmetric total syntheses of two chiral hydroxylated fatty acid derivatives were successfully achieved. The desired stereoisomers could be concisely prepared in mild conditions in a highly convergent manner. Thus, this novel strategy can help stereochemical elucidations of natural

  借助于二乙烯基甲醇的催化去对称化作为一锅不对称诱导和保护烯烃，成功地实现了两种手性羟基化脂肪酸衍生物的不对称全合成。可以在温和条件下以高度收敛的方式简明地制备所需的立体异构体。因此，这种新颖的策略可以帮助对天然产物进行立体化学阐明，由于其在立体生成的仲羟基单元附近的局部对称性，在光谱立体化学分析中存在困难。
• 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。
• Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium
  作者：Patrick S.G. Tassignon、Dick de Wit、Theo C. de Rijk、Laurent F. De Buyck

  DOI：10.1016/0040-4020(95)00747-v

  日期：1995.10

  A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a ‘positive chlorine’ reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of ‘positive chlorine’. 1,9(R)-octadecanediol was

  开发了一种方便，低成本的方法，用于仲醇的选择性氧化，而伯醇的功能保持不变。由氯或甲醇中的三氯异氰尿酸生成的次氯酸甲酯在适当的缓冲剂存在下用作“正氯”试剂，该缓冲剂的酸性足以确保“正氯”的良好转移。将1，9（R）-十八烷二醇以98％的选择性转化为1-羟基-9-十八烷酮。
• 230. Fatty acids. Part I. 9-Hydroxyoctadec-12-enoic acid, a new hydroxy-acid occurring in strophanthus sarmentosus seed oil
  作者：F. D. Gunstone

  DOI：10.1039/jr9520001274

  日期：——
• Optical rotatory dispersion and absolute configuration of some long-chain hydroxy acids
  作者：Thomas H. Applewhite、Ronald G. Binder、William Gaffield

  DOI：10.1021/jo01279a071

  日期：1967.4