(8R)-hydroxystearic acid | 6807-91-6

• 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: (8R)-hydroxystearic acid
• 英文别名: 8-hydroxyoctadecanoic acid；(R)-8-hydroxyoctadecanoic acid；(R)-8-Hydroxy-octadecansaeure；(8R)-8-hydroxyoctadecanoic acid
• CAS: 6807-91-6
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: YYWHSFVJGXJTKD-QGZVFWFLSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  433.9±28.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 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：

  (8R)-hydroxystearic acid 在 吡啶 作用下， 以 溶剂黄146 为溶剂， 反应 55.0h， 生成 methyl (8S)-8-acetoxystearate
  参考文献：
  名称：

  Fahlstadius, Per; Hamberg, Mats, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2027 - 2030

  摘要：

  DOI：
• 作为产物：
  描述：

  Decylmagnesium bromide 在 sodium tetrahydroborate 、 Novozym 435 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 168.08h， 生成 (8R)-hydroxystearic acid
  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

文献信息

• A chemical study of the fruits of three south africanXimenia species, with special reference to the kernel oils
  作者：S. P. Ligthelm、D. H. S. Horn、H. M. Schwartz、M. M. Von Holdt

  DOI：10.1002/jsfa.2740050606

  日期：1954.6

  average composition of the fruits was found to be: fruit pulp 81%, hull 4% and kernel 15%. The high acidity of the fruit juice, 8.6%, was accounted for entirely by citric acid. The kernels contained 64-65% of oil, 18-20% of protein and 4% of fibre. In addition to the acids already found by other workers, a tetracosenoic and an octacosenoic acid were isolated from the kernel oils and a hydroxyoctadecanoic

  发现水果的平均成分为：果肉 81%、外壳 4​​% 和内核 15%。果汁的高酸度为 8.6%，完全由柠檬酸构成。籽粒含有 64-65% 的油、18-20% 的蛋白质和 4% 的纤维。除了其他工作人员已经发现的酸之外，还从仁油中分离出了二十碳烯酸和二十八碳烯酸，并且在一种物种的氢化酸混合物中发现了羟基十八烷酸。三种油类的组成酸组成相似，包括油酸（32.5-40.5%）、西门烯酸（22-24.3%）、二十四烯酸（3.0-7.0%）、六烯酸（西门酸） (3.5-8.7%)、二十二碳烯酸 (4.7-12.2%) 和二十碳烯酸 (lumequeic) (3.0-7.0%)。
• Asymmetric Synthesis of Saturated and Unsaturated Hydroxy Fatty Acids (HFAs) and Study of Their Antiproliferative Activity
  作者：Olga G. Mountanea、Christiana Mantzourani、Dimitrios Gkikas、Panagiotis K. Politis、George Kokotos

  DOI：10.3390/biom14010110

  日期：——

  regioisomers of (R)- and (S)-hydroxypalmitic acids (HPAs) and hydroxystearic acids (HSAs), whose biological activity has not been tested so far, were studied for their antiproliferative activities. The unsaturation of the long chain, as well as an odd-numbered (C17) fatty acid chain, led to reduced activity, while the new 6-(S)-HPA regioisomer was identified as exhibiting potent antiproliferative activity

  羟基脂肪酸 （HFA） 构成一类脂质，其特征是在脂肪长链上存在羟基。本研究旨在扩展我们对 HFA 生物活性的见解，同时也引入了不对称合成不饱和和饱和 HFA 的新方法。同时，我们之前建立的程序被用于生成新的 HFA 区域异构体。采用有机催化步骤合成手性末端环氧化物，其通过炔基化或 Grignard 试剂产生不饱和或饱和的手性仲醇，并最终产生 HFA。首次合成了 7-（S）-羟基油酸 （7SHOA）、7-（S）-羟基棕榈油酸 （7SHPOA） 和 7-（R）- 和 （S）-羟基人造石酸 （7HMA），并与 （R）- 和 （S）-羟基棕榈酸 （HPA） 和羟基硬脂酸 （HSA） 的区域异构体一起研究了其抗增殖活性。长链的不饱和以及奇数 （C17） 脂肪酸链导致活性降低，而新的 6-（S）-HPA 区域异构体被鉴定为在 A549 细胞中表现出有效的抗增殖活性。6SHPA 诱导 A549 细胞中组蛋白
• Ligthelm, Chemistry and industry, 1954, p. 249
  作者：Ligthelm

  DOI：——

  日期：——
• 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.
• Fahlstadius, Per; Hamberg, Mats, Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2027 - 2030
  作者：Fahlstadius, Per、Hamberg, Mats

  DOI：——

  日期：——