methyl (R)-12-hydroxystearate | 6114-39-2

• 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)-12-hydroxystearate
• 英文别名: methyl (R)-12-hydroxyoctadecanoate；Methyl (12R)-12-hydroxyoctadecanoate
• CAS: 6114-39-2
• 化学式: C₁₉H₃₈O₃
• 分子量: 314.509
• InChiKey: RVWOWEQKPMPWMQ-GOSISDBHSA-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

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  methyl (R)-12-hydroxystearate 在 氢氧化钾 、 sodium tetrahydroborate 、 sodium dichromate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 13.0h， 生成 12-羟基硬脂酸
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6
• 作为产物：
  描述：

  蓖麻油酸甲酯 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到methyl (R)-12-hydroxystearate
  参考文献：
  名称：

  Stereostructural analysis of flexible oxidized fatty acids by VCD spectroscopy

  摘要：

  使用VCD光谱学阐明羟基脂肪酸、脂肪环氧化物和脂质过氧化物的绝对构型和构象偏好。

  DOI：

  10.1039/d2cc01337a

文献信息

• Synthesis and desaturation of monofluorinated fatty acids 1
  作者：Peter H. Buist、Kostas A. Alexopoulos、Behnaz Behrouzian、Brian Dawson、Bruce Black

  DOI：10.1039/a701571b

  日期：——

  A series of monofluoro C16 and C18 fatty acids have been synthesized and used as mechanistic probes for fatty acid desaturation. Only fluoroolefinic products are obtained when these compounds are processed by an in vivo Saccharomyces cerevisiae ω9 desaturating system as determined by 1H-decoupled 19F NMR and GC–MS analysis. No evidence for fluorohydrin formation has been found when either methyl (R,S)-9- or 10-fluoropalmitate (stearate) 3a,b and 5a,b was incubated with the ω9 desaturase. On desaturation α- and β-fluorine substituent effects (kH/kF) of magnitude 6.2 and 2.4, respectively, have been measured by direct competition experiments between 3a and 3b and between methyl 16-fluoropalmitate 3c and 3b. These results do not support the involvement of discrete hydroxylated and carbocationic intermediates in fatty acid desaturation. Substantial apparent steric effects have been observed for monofluorostearoyl substrates 5c–f bearing a fluorine distal from the site of initial oxidation. In the case of (R,S)-methyl 12-fluorostearate 5f, we show that both enantiomers are desaturated at comparable rates.

  一系列单氟代的C16和C18脂肪酸已被合成并作为机制探针用于脂肪酸脱饱和的研究。当这些化合物经过体内酿酒酵母ω9脱饱和系统处理后，根据1H去耦19F核磁共振和气相色谱-质谱分析，仅得到了含氟烯烃的产物。无论是甲基（R,S）-9-还是10-氟代棕榈酸（硬脂酸）3a,b和5a,b与ω9脱饱和酶共孵育时，均未发现形成氟醇的迹象。在脱饱和过程中，通过3a与3b以及甲基16-氟代棕榈酸3c与3b之间的直接竞争实验，分别测得α-和β-氟代取代基效应（kH/kF）大小为6.2和2.4。这些结果不支持脂肪酸脱饱和过程中涉及离散的羟基化和碳正离子中间体。对于远离初始氧化位点的氟代硬脂酰基底物5c–f，观察到了显著的表观立体效应。就（R,S）-甲基12-氟代硬脂酸5f而言，我们证明了两种对映体以相近速率进行脱饱和。
• (<i>R</i>)-12-Hydroxystearic Acid Hydrazides as Very Efficient Gelators: Diffusion, Partial Thixotropy, and Self-Healing in Self-Standing Gels
  作者：Jingjing Li、Mohan Zhang、Richard G. Weiss

  DOI：10.1002/asia.201601163

  日期：2016.12.6

  properties of derivatives of N‐alkylated (R)‐12‐hydroxystearic acid hydrazide (n‐HSAH, n=0, 2, 6, 10; n is the length of an n‐alkyl chain on the terminal nitrogen atom) in a wide variety of liquids is reported. The n‐HSAH compounds were derived from a naturally occurring alkanoic acid, (R)‐12‐hydroxystearic acid (R‐12HSA), and although they differ from the analogous N‐alkyl (R)‐12‐hydroxystearamides (n‐HSAA)

  N-烷基化的（R）-12-羟基硬脂酸酰肼衍生物（n- HSAH，n = 0，2，6，10 ; n是末端氮原子上的n-烷基链的长度）的胶凝特性据报道有各种各样的液体。所述Ñ -HSAH化合物从天然存在的链烷酸，（派生- [R）-12-羟基硬脂酸（ř -12HSA），尽管它们从类似的不同N-烷基（[R）-12- hydroxystearamides（Ñ‐HSAA）仅存在一个N-H基团，它们作为胶凝剂的行为就大不相同。例如，母体分子（0-HSAH）是乙二醇的超级胶凝剂，它在其中形成可自我修复，部分触变，可塑和承重的自立式凝胶。0-HSAA凝胶不是自立的。0-HSAH是结构上最简单的分子胶凝剂，我们知道它能够形成自立和部分触变凝胶。而且，阳离子染料赤藓红B和阴离子染料亚甲基蓝在0-HSAH /乙二醇凝胶嵌段中的扩散比乙二醇的自扩散慢得多。偏光光学显微镜，X射线衍射和FTIR研究表明，凝胶的自组装原
• [EN] (R)-12-HYDROXYSTEARIC ACID HYDRAZIDES AS GELATORS AND SELF-STANDING GELS THEREOF<br/>[FR] HYDRAZIDES D'ACIDE (R)-12-HYDROXYSTÉARIQUE UTILISÉS COMME GÉLIFIANTS ET LEURS GELS AUTOPORTEURS
  申请人：UNIV GEORGETOWN

  公开号：WO2017117212A1

  公开（公告）日：2017-07-06

  (R)-12-hydroxystearic acid hydrazides as gelators and gels generated therefrom are provided. A series of (R)-12-hydroxystearic acid hydrazides produce gels that are self-standing and self-healing. The (R)-12-hydroxystearic acid hydrazides are capable of exhibiting gelling properties in a wide variety of solvents. The gels have demonstrated good potential for use in drug release.

  提供(R)-12-羟基硬脂酸腙作为凝胶剂及由此产生的凝胶。一系列(R)-12-羟基硬脂酸腙产生的凝胶具有自立和自修复性质。这些(R)-12-羟基硬脂酸腙能够在各种溶剂中展现凝胶特性。这些凝胶已经展示出在药物释放中的潜力。
• Fatty acid composition of Prosopis cineraria seeds
  作者：S. Gangal、S. Sharma、A. Rauf

  DOI：10.1007/s10600-009-9425-8

  日期：2009.9

  fatty acid was also helpful in assigning the structure. It showed a characteristic signal at δ 172.2 for carbonyl carbon, 130.1 attributed to C-9 and C-10, 29.4 (C-8), 31.5 (C-11), 71.5 (C-12), 33.8 (C-13), and 51.4 (OCH3). The acetate derivative of the pure hydroxy ester showed a strong band at 1235 cm–1 and no hydroxyl absorption band in its IR spectrum. The 1H NMR spectrum (acetate derivative) showed

  Prosopis 属豆科植物含羞草亚科，共有 44 种，主要分布于干旱、半干旱、热带和亚热带国家[1]。在世界的许多沙漠地区，Prosopis 物种的种子已被提议作为人类和动物经济食品的农业工业发展的来源 [2, 3]。此外，种子和豆荚已在传统医学中用于治疗多种疾病 [4, 5]。以前曾报道过糖类、黄酮酮、脂肪酸、心材中的单宁 [1]、黄酮、花中的糖苷 patulitrin [6] 和哌啶 3-醇生物碱 [7]。继续我们之前对各种种子油和羟基脂肪酸鉴定的研究 [8]，对 P. 种子油的研究。已经对其成分脂肪酸进行了分析，并确认了这种种子油中是否存在羟基脂肪酸。油和种子的分析值（表 1）是根据 AOCS 推荐的程序确定的 [9]。种子油对 Halphen 试验 [10]、2,4-二硝基苯肼薄层色谱试验 [11] 和苦味酸 TLC 试验 [12] 没有反应，从而表明不存在环丙烯、酮和环氧脂肪酸
• Biomolecule-derived supported cobalt nanoparticles for hydrogenation of industrial olefins, natural oils and more in water
  作者：Anahit Pews-Davtyan、Florian Korbinian Scharnagl、Maximilian Franz Hertrich、Carsten Kreyenschulte、Stephan Bartling、Henrik Lund、Ralf Jackstell、Matthias Beller

  DOI：10.1039/c9gc01276a

  日期：——

  application in hydrogenations of a wide range of terminal and internal carbon–carbon double bonds in water under mild conditions. Catalysts are prepared on multi-gram scale by pyrolysis of cobalt acetate and uracil, guanine, adenine or L-tryptophan. The most active material Co-Ura/C-600 showed good productivity in industrially relevant hydrogenation of diisobutene to isooctane and in natural oil hardening

  在化学工业中，使用贵金属催化剂或发火的RANEY®镍对烯烃进行催化加氢非常重要。从绿色和可持续化学的观点出发，非常需要设计和开发富含地球，毒性较小且对环境更友好的催化剂。在这里，我们报道了活性钴催化剂的方便制备方法及其在温和条件下在水中广泛的末端和内部碳-碳双键加氢中的应用。通过乙酸钴和尿嘧啶，鸟嘌呤，腺嘌呤或L-色氨酸的热解，以克为单位制备催化剂。活性最高的材料Co-URA / C-600在与工业相关的二异丁烯加氢制异辛烷和天然油硬化方面显示出良好的生产率。