4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸 | 5762-36-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸
• 英文名称: R-12-hydroxyoctadecanoic acid
• 英文别名: (R)-12-hydroxystearic acid；12-hydroxy stearic acid；(R)-12-HSA；(R)-12-Hydroxyoctadecanoic acid；(12R)-12-hydroxyoctadecanoic acid
• CAS: 5762-36-7
• 化学式: C₁₈H₃₆O₃
• 分子量: 300.482
• InChiKey: ULQISTXYYBZJSJ-QGZVFWFLSA-N

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：

  4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸 在 氢氧化钾 、 sodium tetrahydroborate 、 sodium dichromate 、 硫酸 、 三氟化硼 、 溶剂黄146 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 13.33h， 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：

  1-碘己烷 在 过氧乙酸 、 氢氧化钾 、 乙醚 、 三氟化硼 、 lithium diisopropyl amide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸
  参考文献：
  名称：

  An asymmetric synthesis of acyclic and macrocyclic .alpha.-alkyl ketones. The role of (e)- and (z)-lithioenamines

  摘要：

  DOI：

  10.1021/ja00401a029
• 作为试剂：
  描述：

  chloroauric acid 在 4-[4-(乙酰基氨基)苯胺基]-1-氨基-9,10-二氢-9,10-二羰基蒽-2,6-二磺基酸 、 N-(2-aminoethyl)-3-((2-(2-aminoethylcarbamoyl)ethyl)octadecylamino)propionamide 、 lithium hydroxide 、 lithium chloride 、 维生素 C 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 生成 gold
  参考文献：
  名称：

  双螺旋金纳米线的手性控制合成

  摘要：

  使用湿化学方法选择性大规模合成具有复杂形状的贵金属纳米晶体仍然是令人兴奋的挑战。在这里，我们报告了使用手性软模板合成双螺旋金纳米线 (NW) 的手性可控合成，该模板由两种具有各自活性功能的有机凝胶剂组成；一种有机凝胶剂用于将螺旋性引入模板，另一种用作封端剂以控制 Au 形状。将两种有机凝胶剂在含有少量甲苯的水中混合，然后加入 LiCl，即可简单地制备一维扭曲纳米带模板；通过选择螺旋性诱导有机凝胶剂的旋向性来控制模板手性。在这些手性模板上合成的双螺旋 Au NW 具有与模板相同的螺旋结构，因为 Au NW 沿着具有右手或左手螺旋的扭曲纳米带的两个边缘生长。右手和左手双螺旋金纳米线的色散表现出相反的 CD 信号。

  DOI：

  10.1021/jacs.8b00910

文献信息

• [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。
• Influence of Positional Isomers on the Macroscale and Nanoscale Architectures of Aggregates of Racemic Hydroxyoctadecanoic Acids in Their Molecular Gel, Dispersion, and Solid States
  作者：Shibu Abraham、Yaqi Lan、Ricky S. H. Lam、Douglas A. S. Grahame、Jennifer Jae Hee Kim、Richard G. Weiss、Michael A. Rogers

  DOI：10.1021/la204412t

  日期：2012.3.20

  Inter/intramolecular hydrogen bonding of a series of hydroxystearic acids (HSAs) are investigated. Self-assembly of molecular gels obtained from these fatty acids with isomeric hydroxyl groups is influenced by the position of the secondary hydroxyl group. 2-Hydroxystearic acid (2HSA) does not form a molecular dimer, as indicated by FT-IR, and growth along the secondary axis is inhibited because the secondary hydroxyl

  研究了一系列羟基硬脂酸（HSA）的分子间/分子间氢键。由这些具有异构羟基的脂肪酸获得的分子凝胶的自组装受到仲羟基位置的影响。如FT-IR所示，2-羟基硬脂酸（2HSA）不会形成分子二聚体，并且由于仲羟基无法形成分子间的H键，因此沿仲轴的生长受到抑制。同样，XRD长间隔短于羟基硬脂酸的二聚体长度。3-羟基硬脂酸（3HSA）形成无环二聚体，并且羟基无法氢键结合，从而阻止了晶体结构沿副轴生长。最后，异构体6HSA，8HSA，10HSA，12HSA和14HSA具有相似的XRD和FT-IR模式，这表明这些分子都以相似的方式自组装。单体形成羧基环状二聚体，并且仲羟基促进沿仲轴的生长。
• Enzymatic esterification of glycerol III. Lipase‐catalyzed synthesis of regioisomerically pure 1,3‐<i>sn</i>‐diacylglycerols and 1 (3)‐<i>rac</i>‐monoacylglycerols derived from unsaturated fatty acids
  作者：Claudia Waldinger、Manfred Schneider

  DOI：10.1007/bf02523518

  日期：1996.11

  Lipases that display high regioselectivities and broad substrate tolerance were used as catalysts for the efficient esterification of glycerol under the conditions of irreversible acyl transfer. A variety of unsaturated fatty acids, such as oleic, linoleic, erucic, ricinolic, hydroxystearic and coriolic acid, were used for this purpose in the form of their vinyl esters. Suitable biocatalysts were chosen on the basis of systematic screening experiments regarding their regioselectivities (RE) and substrate tolerances. Distinct differences were found and expressed in numerical RE values as a measure for differences of these biocatalysts as being specific, selective, and nonspecific. Based on these experiments, a variety of molecules were synthesized on a preparative scale (>150 mmol) in good yield (ca.85%) and with high regioisomerical purities (>95% RE).

  摘要 利用具有高区域选择性和广泛底物耐受性的脂肪酶作为催化剂，在不可逆酰基转移条件下对甘油进行高效酯化。油酸、亚油酸、芥酸、蓖麻酸、羟基硬脂酸和科里奥利酸等多种不饱和脂肪酸以乙烯基酯的形式被用于此目的。在对生物催化剂的区域选择性（RE）和底物耐受性进行系统筛选的基础上，选择了合适的生物催化剂。实验发现，这些生物催化剂在特异性、选择性和非特异性方面存在明显差异，并以 RE 数值表示。在这些实验的基础上，以制备规模（150 毫摩尔）合成了多种分子，产率高（约 85%），区域异构纯度高（95% RE）。
• Influence of chirality on the modes of self-assembly of 12-hydroxystearic acid in molecular gels of mineral oil
  作者：Douglas A. S. Grahame、Caitlin Olauson、Ricky S. H. Lam、Tor Pedersen、Ferenc Borondics、Shibu Abraham、Richard G. Weiss、Michael A. Rogers

  DOI：10.1039/c1sm05757j

  日期：——

  The gelating abilities of enantiopure, racemic, and different enantio-enriched mixtures of 12-hydroxystearic acid (12HSA) have been compared in order to clarify conflicting reports in the literature (1) concerning their ability to gelate organic liquids. Less than 1.0 wt % of optically pure (D)-12HSA was found to gelate mineral oil. The gel matrix was comprised of high aspect ratio fibers in which the 12HSA molecules were organized as head-to-head dimers and the 12-hydroxyl groups formed an H-bonding network along the axis transverse to the longitudinal growth. Below 2 wt %, racemic 12HSA in mineral oil did not reach the percolation threshold. Its organogels were comprised of platelet-like crystals with a molecular arrangement of single, in-plane, hydrogen-bonded acyclic dimers that prevent longitudinal growth and limit the ability of the polar groups to phase separate during nucleation.

  我们比较了对映体纯品、外消旋体和不同对映体富集的 12- 羟基硬脂酸（12HSA）混合物的凝胶能力，以澄清文献 (1) 中关于其凝胶有机液体能力的相互矛盾的报道。研究发现，光学纯度低于 1.0 wt % 的 (D)-12HSA 能使矿物油凝胶化。凝胶基质由高纵横比纤维组成，其中 12HSA 分子组织成头对头二聚体，12-羟基沿纵向横轴形成 H 键网络。矿物油中外消旋 12HSA 的重量比低于 2 wt % 时，达不到渗流阈值。其有机凝胶由血小板状晶体组成，分子排列为单个平面内氢键无环二聚体，阻止了纵向生长，并限制了极性基团在成核过程中的相分离能力。
• Studies of Helical Aggregates of Molecules. I. Enantiomorphism in the Helical Aggregates of Optically Active 12-Hydroxystearic Acid and Its Lithium Salt
  作者：Taro Tachibana、Hideko Kambara

  DOI：10.1246/bcsj.42.3422

  日期：1969.12

  It was found, by electron-microscope observation, that d(or l)-12-hydroxystearic acid and its Li soap crystallize from a solution in various solvents in the form of a twisted fiber. The twist was left-handed for the d-acid and right-handed for the l-acid, while the Li soap gave results just opposite to those of the corresponding acid. The Dl-acid separated out not fibers, but platelike crystals, and its Li soap produced non-twisted fibers. Thus, an enantiomorphic relationship for the sense of twist between the d-enantiomer and the l-enantiomer was found both for the acid and for the Li soap.

  通过电子显微镜观察发现，d（或 l）-12-羟基硬脂酸及其锂皂从各种溶剂的溶液中结晶出来时呈扭曲的纤维状。d-酸的扭曲是左旋的，l-酸的扭曲是右旋的，而锂皂的结果与相应酸的结果正好相反。Dl-酸分离出的不是纤维，而是板状晶体，而其锂皂则产生非扭曲纤维。因此，在酸和锂皂中都发现了 d-对映体和 l-对映体之间的捻度对映关系。