10-hydroxyoctadecanoic acid | 67042-09-5

• 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: 10-hydroxyoctadecanoic acid
• 英文别名: (10S)-10-hydroxyoctadecanoic Acid；10-(S)-hydroxyoctadecanoic acid；(S)-10-hydroxyoctadecanoic acid；10-hydroxystearic acid；(S)-10-hydroxystearic acid；10-Hydroxystearic acid, (10S)-；(10S)-10-hydroxyoctadecanoic acid
• CAS: 67042-09-5
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: PAZZVPKITDJCPV-KRWDZBQOSA-N

物化性质

• 沸点：
  436.3±18.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-hydroxyoctadecanoic acid 在 重氮甲烷 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl (S)-10-((R)-2-acetoxy-2-phenylacetoxy)octadecanoate
  参考文献：
  名称：

  Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation

  摘要：

  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.

  DOI：

  10.1016/j.molcatb.2012.06.017
• 作为产物：
  描述：

  10,11-dibromo-undecanoic acid 在 titanium(IV) isopropylate 、 氧气 、 sodium hydride 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 苏丹红 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 39.67h， 生成 10-hydroxyoctadecanoic acid
  参考文献：
  名称：

  通过不对称催化合成“手性” 10-羟基硬脂酸的构型分配

  摘要：

  报道了（S）-10-羟基硬脂酸（1）的不对称催化全合成，用于比较其绝对构型与通过油酸发酵水合获得的样品的绝对构型。合成涉及两个催化关键步骤，即Ru催化的9-癸癸酸（7）到10-氧代十二烷酸（5）的反马尔科夫尼科夫水合，然后是钛介导的不对称催化的二辛基锌（25）到5 in手性配体N，N' -（（（1 R，2 R）-环己烷-1,2-二基）双（1,1,1-三氟甲磺酰胺）的存在（6）。合成是短而有效的，并且避免使用保护基。将10-十一碳烯酸（9）臭氧分解为5可以为合成路线提供一个替代的入口点。以10,11-二溴代正癸酸（11）为模型底物，并使用qNMR定量分析所有反应产物，研究了在各种条件下（ω，ω -1）-二溴链烷酸向ω-链烷酸的双脱氢溴化反应。本文介绍的合成方法有可能被推广到各种n-羟基脂肪酸的不对称催化合成中。

  DOI：

  10.1002/hlca.201600242

文献信息

• 光学活性なヒドロキシ脂肪酸の製造方法
  申请人：アサヒグループホールディングス株式会社

  公开号：JP2017100988A

  公开（公告）日：2017-06-08

  【課題】多様な構造を有する生成物に適用でき、且つ低製造コスト及び高立体選択性である、光学活性なヒドロキシ脂肪酸を製造する手段を提供することを課題とする。【解決手段】本発明は、式（I-1）：で表される化合物の製造方法であって、炭素鎖連結工程、第二酸化工程、立体選択的還元工程、及び第三酸化工程を含む、前記方法に関する。本発明はまた、式（I-2）：で表される化合物の製造方法であって、炭素鎖連結工程、速度論的光学分割工程、及び第三酸化工程を含む、前記方法に関する。【選択図】なし

  The task is to provide a method for producing optically active hydroxy fatty acids that can be applied to products with various structures, have low manufacturing costs, and high stereoselectivity. The solution involves a method for producing compounds represented by formula (I-1) comprising carbon chain linking, a second oxidation process, stereoselective reduction process, and a third oxidation process. The invention also includes a method for producing compounds represented by formula (I-2) comprising carbon chain linking, a kinetically controlled optical resolution process, and a third oxidation process. No figures are included.
• Saturated Hydroxy Fatty Acids Exhibit a Cell Growth Inhibitory Activity and Suppress the Cytokine-Induced β-Cell Apoptosis
  作者：Maroula G. Kokotou、Alexandros C. Kokotos、Dimitrios Gkikas、Olga G. Mountanea、Christiana Mantzourani、Abdulaziz Almutairi、Xiaoyong Lei、Sasanka Ramanadham、Panagiotis K. Politis、George Kokotos

  DOI：10.1021/acs.jmedchem.0c00844

  日期：2020.11.12

  families of previously unrecognized saturated hydroxy fatty acids (SHFAs), namely, hydroxystearic and hydroxypalmitic acids, consisting of isomers with the hydroxyl group at different positions, were identified in milk. Among the various regio-isomers synthesized, those carrying the hydroxyl at the 7- and 9-positions presented growth inhibitory activities against various human cancer cell lines, including

  生物活性脂质的领域不断扩大，发现了促进人类健康的新型脂质分子。通过脂质组学方法，在牛奶中鉴定了两个新的先前无法识别的饱和羟基脂肪酸（SHFA）家族，即羟基硬脂酸和羟基棕榈酸，它们由羟基位置不同的异构体组成。在合成的各种区域异构体中，那些在7和9位带有羟基的异构体表现出针对各种人类癌细胞系（包括A549，Caco-2和SF268细胞）的生长抑制活性。此外，7-和9-羟基硬脂酸能够抑制促炎性细胞因子诱导的β细胞凋亡，从而增加了它们在抵抗自身免疫性疾病（例如1型糖尿病）中的可能性。7-（R）-羟基硬脂酸在抑制细胞生长和抑制β细胞死亡方面均显示出最高的效力。我们建议，这种天然存在的SHFA可能在促进和保护人类健康中发挥作用。
• 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.
• Configurational Assignment of ‘Cryptochiral’ 10-Hydroxystearic Acid Through an Asymmetric Catalytic Synthesis
  作者：Andreas Brunner、Lukas Hintermann

  DOI：10.1002/hlca.201600242

  日期：2016.12

  An asymmetric catalytic total synthesis of (S)‐10‐hydroxystearic acid (1) for comparison of its absolute configuration to that of samples obtained by fermentative hydration of oleic acid is reported. The synthesis involves two catalytic key‐steps, namely Ru‐catalyzed anti‐Markovnikov hydration of 9‐decynoic acid (7) to 10‐oxodecanoic acid (5), followed by titanium‐mediated asymmetric catalytic addition

  报道了（S）-10-羟基硬脂酸（1）的不对称催化全合成，用于比较其绝对构型与通过油酸发酵水合获得的样品的绝对构型。合成涉及两个催化关键步骤，即Ru催化的9-癸癸酸（7）到10-氧代十二烷酸（5）的反马尔科夫尼科夫水合，然后是钛介导的不对称催化的二辛基锌（25）到5 in手性配体N，N' -（（（1 R，2 R）-环己烷-1,2-二基）双（1,1,1-三氟甲磺酰胺）的存在（6）。合成是短而有效的，并且避免使用保护基。将10-十一碳烯酸（9）臭氧分解为5可以为合成路线提供一个替代的入口点。以10,11-二溴代正癸酸（11）为模型底物，并使用qNMR定量分析所有反应产物，研究了在各种条件下（ω，ω -1）-二溴链烷酸向ω-链烷酸的双脱氢溴化反应。本文介绍的合成方法有可能被推广到各种n-羟基脂肪酸的不对称催化合成中。