methyl (S)-10-hydroxystearate | 423184-30-9

• 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 (S)-10-hydroxystearate
• 英文别名: methyl (10S)-10-hydroxyoctadecanoate
• CAS: 423184-30-9
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: ZWOMTUQOMSFPSL-SFHVURJKSA-N

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 (S)-10-hydroxystearate 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 (10R)-[10-2H]-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：

  10,11-dibromo-undecanoic acid 在 titanium(IV) isopropylate 、 盐酸 、 氧气 、 sodium hydride 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 sodium hydroxide 、 苏丹红 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 57.67h， 生成 methyl (S)-10-hydroxystearate
  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

• Fungal β‐Mannosyloxymannitol Glycolipids and Their Analogues: Synthesis and Mincle‐Mediated Signaling Activity
  作者：Takanori Matsumaru、Kasumi Sakuratani、Saeko Yanaka、Koichi Kato、Sho Yamasaki、Yukari Fujimoto

  DOI：10.1002/ejoc.202200109

  日期：2022.5.25

  The diastereomeric pair of mannosyloxymannitol glycolipids and its analogues were synthesized and analyzed for the structure–Mincle-mediated signaling activity relationships. The results suggest that the dimannosyloxy fatty acid moiety of the mannosyloxymannitol glycolipid plays a major role in the molecular recognition of Mincle.

  合成了非对映异构体对的甘露糖氧基甘露醇糖脂及其类似物，并分析了结构-Mincle 介导的信号活性关系。结果表明，甘露糖氧基甘露醇糖脂的二甘露糖氧基脂肪酸部分在Mincle的分子识别中起主要作用。
• 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.
• Seo, Chull Won; Yamada, Yasuhiro; Takada, Nobuo, Agricultural and Biological Chemistry, 1981, vol. 45, # 9, p. 2025 - 2030
  作者：Seo, Chull Won、Yamada, Yasuhiro、Takada, Nobuo、Okada, Hirosuke

  DOI：——

  日期：——