7-hydroxyoctadecanoic acid

• 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: 7-hydroxyoctadecanoic acid
• 英文别名: (S)-7-hydroxyoctadecanoic acid；(7S)-7-hydroxyoctadecanoic acid
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: AROVHWXXFTUQIL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 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：

  7-hydroxyoctadecanoic acid 在 重氮甲烷 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl (7S)-7-{[(2R)-2-(acetyloxy)-2-phenylacetyl]oxy}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：

  8-(benzyloxy)octanal 在 吡啶 、 copper(l) iodide 、 Jones reagent 、 palladium 10% on activated carbon 、 2,3,4,5,6,6-六氯-2,4-环己二烯-1-酮 、 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one trifluoroacetate 、 氢气 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 51.25h， 生成 7-hydroxyoctadecanoic acid
  参考文献：
  名称：

  饱和羟基脂肪酸表现出细胞生长抑制活性并抑制细胞因子诱导的β细胞凋亡。

  摘要：

  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。

  DOI：

  10.1021/acs.jmedchem.0c00844

文献信息

• An Easy Route to Enantiomerically Enriched 7- and 8-Hydroxy­stearic Acids by Olefin-Metathesis-Based Approach
  作者：Patrizia Nitti、Carla Boga、Sara Drioli、Cristina Forzato、Gabriele Micheletti、Fabio Prati

  DOI：10.1055/s-0035-1561570

  日期：——

  The synthesis of enantiomerically enriched 7- and 8-hydroxy­stearic acids (7- and 8-HSA) has been successfully accomplished starting from chiral nonracemic 1-pentadecen-4-ol and 1-tetradecen-4-ol, respectively. Their Yamaguchi’s esterification with 4-pentenoic and 5-hexenoic acids, respectively, afforded the suitable dienic esters which were submitted to ring-closing metathesis reaction. After hydrogenation

  分别从手性非外消旋 1-十五碳烯-4-醇和 1-十四碳烯-4-醇开始，已成功合成富含对映异构体的 7-和 8-羟基硬脂酸（7-和 8-HSA）。它们分别与 4-戊烯酸和 5-己烯酸的 Yamaguchi 酯化反应得到合适的二烯酯，然后进行闭环复分解反应。在复杂反应混合物的氢化和碱水解后，以约 40% 的总产率获得手性非外消旋 7- 和 8-HSA。
• 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.
• 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。