benzoic acid * β-cyclodextrin | 68419-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzoic acid * β-cyclodextrin
• 英文别名: β-Cyclodextrin/Benzoesaeure；benzoic acid;(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 68419-51-2
• 化学式: C₇H₆O₂*C₄₂H₇₀O₃₅
• 分子量: 1257.12
• InChiKey: GIXYPVGUSZVLLP-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.85
• 重原子数：
  86.0
• 可旋转键数：
  8.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  591.35
• 氢给体数：
  22.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  benzoic acid * β-cyclodextrin 在 phosphate buffer 作用下， 以 重水 为溶剂， 生成 苯甲酸 、 β-环糊精
  参考文献：
  名称：

  Thermodynamic and Nuclear Magnetic Resonance Study of the Reactions of α- and β-Cyclodextrin with Acids, Aliphatic Amines, and Cyclic Alcohols

  摘要：

  Titration calorimetry was used to determine equilibrium constants and standard molar enthalpy, Gibbs energy, and entropy changes for the reactions of a series of acids, amines, and cyclic alcohols with alpha- and beta-cyclodextrin. The results have been examined in terms of structural features in the ligands such as the number of alkyl groups, the charge number, the presence of a double bond, branching, and the presence of methyl and methoxy groups. The values of thermodynamic quantities, in particular the standard molar Gibbs energy, correlate well with the structural features in the ligands. These structural correlations can be used for the estimation of thermodynamic quantities for related reactions. Enthalpy-entropy compensation is evident when the individual classes of substances studied herein are considered, but does not hold when these various classes of ligands are considered collectively. The NMR results indicate that the mode of accommodation of the acids and amines in the alpha-cyclodextrin cavity is very similar, but that the 1-methyl groups in 1-methylhexylamine and in 1-methylheptylamine and the N-methyl group in N-methylhexylamine lie outside the alpha-cyclodextrin cavity. This latter finding is consistent with the calorimetric results. Many of the thermodynamic and NMR results can be qualitatively understood in terms of van der Waals forces and hydrophobic effects.

  DOI：

  10.1021/jp962715n
• 作为产物：
  描述：

  苯甲酸 、 butyl β-cyclodextrin 在 水 作用下， 反应 4.0h， 以73%的产率得到benzoic acid * β-cyclodextrin
  参考文献：
  名称：

  单取代β-环糊精衍生物包合物形成的特点

  摘要：

  摘要 在尝试获得包含酯和醚键的 β-环糊精的一系列单衍生物与某些芳香族和脂肪族羧酸的包合物时，已经获得了意想不到的客体包合物，推测是由于客体被预先包合到β-环糊精腔。包合物的结构和组成已通过1 H 和13 C NMR 光谱证实。

  DOI：

  10.1134/s107036322106013x

文献信息

• Ultrasonic Relaxation Associated with Inclusion Complex of Drugs and β-Cyclodextrin
  作者：Sadakatsu Nishikawa、Minako Kondo、Eri Kamimura、Shaoyong Xing

  DOI：10.1246/bcsj.80.694

  日期：2007.4.15

  in aqueous solutions in terms of ultrasonic absorption in the frequency range from 0.8 to 95 MHz. A single relaxational absorption was found when the host and the guest were coexisting in water. Ultrasonic relaxation parameters were determined as a function of the guest concentration. From the concentration dependence of the parameters, the cause of the relaxation was attributed to a perturbation of

  β-环糊精（β-CD）（宿主）和水杨酸（客体）在 pH ≈6 和 ≈S 之间以及 β-CD 和苯甲酸（客体）在 pH ≈6 时的动态相互作用在水溶液中进行了研究在 0.8 到 95 MHz 频率范围内的超声波吸收。当主人和客人在水中共存时，发现了单一的弛豫吸收。超声波弛豫参数被确定为客体浓度的函数。从参数的浓度依赖性来看，弛豫的原因归因于与主体和客体形成的包合物相关的平衡的扰动。前向和后向速率常数，主客体络合反应的平衡常数和标准体积变化由弛豫频率和每个波长的最大吸收的酸浓度依赖性确定。将结果与含有阿司匹林和 β-CD 的溶液中的结果进行比较。发现在邻位取代苯甲酸的解离形式中，取代基对速率和热力学参数的影响不显着。然而，羧基对参数的电荷效应被确定为显着促进由酸和 β-CD 形成的复合物的稳定性以及酸离开 β-CD 腔的速率常数。发现在邻位取代苯甲酸的解离形式中，取代基对速率和热力学参数的影响
• Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
  作者：Santiago García Méndez、Francisco J. Otero Espinar、Asteria Luzardo Alvarez、Marcela R. Longhi、Mario A. Quevedo、Ariana Zoppi

  DOI：10.1007/s10847-016-0603-6

  日期：2016.6

  solubility analyses were performed to determine the relative binding affinities for binary (BA:β-CD and HA:βCD) and ternary (BA:β-CD:AA) complexes, obtaining the following results: BA:β-CD:AA > BA:β-CD: > HA:β-CD. As part of the structural elucidation of the studied complexes, their spatial configurations were determined by NMR and further characterized applying molecular modeling (i.e., molecular docking

  摘要 β-环糊精（β-CD）是众所周知的用于制备包合物的宿主分子。考虑到这些复合物的三维排列取决于 β-CD 腔内客体分子的包含模式，因此非常需要开发阐明其结构的方法。这项工作的主要目的是阐明与氨基酸（AA：甘氨酸、缬氨酸、异亮氨酸、精氨酸和谷氨酸）作为第三组分对苯甲酸 (BA) 与 β 络合的影响相关的结构和能量特征-光盘。此外，马尿酸 (HA)，一种类似于 BA-甘氨酸缀合物的结构，作为模型分子被包括在内，以比较甘氨酸作为与客体分子共价连接的化学部分存在的影响。进行相溶解度分析以确定二元 (BA:β-CD 和 HA:βCD) 和三元 (BA:β-CD:AA) 复合物的相对结合亲和力，获得以下结果：BA:β-CD:AA > BA:β-CD: > HA:β-CD。作为所研究复合物结构阐明的一部分，它们的空间构型由 NMR 确定，并应用分子建模（即分子对接和分子动力学）技术进一步表征。两种方法都证明
• Rapid analysis of drug binding to β-cyclodextrin: part II substituents effect on physicochemical and co-conformational stability of drug/cyclodextrin complex
  作者：Ali Aboel Dahab

  DOI：10.1039/c3ra47010e

  日期：——

  In the pharmaceutical industry, the most common application of cyclodextrins (CyDs) is to enhance the solubility, stability, safety and bioavailability of drug molecules. Although, there have been many reports on the complexation of drugs with cyclodextrins, to date, CyDs interaction with drugs is not well understood. The purpose of this work is to show the successful applications of previous work employing a novel, versatile, compact, low-volume, routine apparatus, which consists of a pump, flask and a rotating cell holder for the simultaneous measurements of absorbance and circular dichroism (CD) that allows for the concurrent use of four different pathlengths for binding studies. To show the effect of substituents on drug/CyD binding, benzoic acid as an important precursor for the synthesis of many other organic substances and benzoic acid derivatives were used in this study. Also, an effective novel method for binding titration was employed. The pKa, binding constants, stoichiometry and structural co-conformations of benzoic acid and derivatives/β-CyD complexes were elucidated and determined with accuracy. Substituents type and location show a significant effect on the extent of binding and physicochemical properties of the binding complex. The system proved efficiency, ability to be used routinely and the analysis time was reduced significantly to less than one fourth of the total analysis time used in conventional methods, with possible automation for high-throughput analysis.

  在制药行业中，环糊精（CyDs）最常见的应用是增强药物分子的溶解度、稳定性、安全性和生物利用度。尽管关于药物与环糊精络合的报道很多，但迄今为止，CyDs与药物的相互作用尚不清楚。这项工作的目的是展示以前工作的成功应用，采用一种新颖的、多功能的、紧凑的、小体积的常规装置，该装置由泵、烧瓶和旋转池支架组成，用于同时测量吸光度和圆二色性（CD）允许同时使用四种不同的光程进行结合研究。为了显示取代基对药物/CyD 结合的影响，本研究使用苯甲酸作为合成许多其他有机物质和苯甲酸衍生物的重要前体。此外，还采用了一种有效的新结合滴定方法。准确地阐明和确定了苯甲酸和衍生物/β-CyD 复合物的pKa、结合常数、化学计量和结构共构象。取代基的类型和位置对结合复合物的结合程度和物理化学性质有显着影响。事实证明，该系统效率高，能够常规使用，分析时间显着缩短至不到传统方法总分析时间的四分之一，并且可以实现高通量分析的自动化。
• Complexation of Cyclodextrins with Benzoic Acid in Water-Organic Solvents: A Solvation-Thermodynamic Approach
  作者：Tatyana R. Usacheva、Vitaly A. Volynkin、Viktor T. Panyushkin、Dmitry A. Lindt、Thi Lan Pham、Thi Thu Ha Nguyen、Thi My Hanh Le、Diana A. Alister、Dzhovidon N. Kabirov、Natalya N. Kuranova、George A. Gamov、Roman A. Kushnir、Marco Biondi、Concetta Giancola、Valentin A. Sharnin

  DOI：10.3390/molecules26154408

  日期：——

  contributions into the Gibbs energy changes of the [BA⊂β-CD] molecular complex formation. Quantum chemical calculations of the interaction energy between β-CD and BA as well as the structure of the [BA⊂β-CD] complex and the energy of β-CD and BA interaction in vacuum and in the medium of water, methanol and dimethylsulfoxide solvents are carried out. The stability of [BA⊂β-CD] complex in H2O-EtOH and H2O-DMSO solvents

  本研究的目的是获得有关 β-环糊精 (β-CD) 和苯甲酸 (BA) 之间络合的新数据，作为疏水分子与环糊精 (CD) 在各种介质中形成复合物的模型反应。这项研究可以通过选择合适的溶剂混合物来帮助开发基于环糊精的药物制剂，该溶剂混合物可用于工业应用，旨在控制液相反应/过程。在本文中，BA 和 β-CD ([BA⊂β-CD]) 在 D 2 O-DMSO- d 6和 D 2 O-EtOH 中形成的分子配合物的核磁共振结果表明配合物的稳定性在 H 2 O-DMSO- d 6在实验误差内变化，而 H 2 O-EtOH减少。BA 在水和水-二甲亚砜混合物中的 Gibbs 能量变化已经获得，并已用于分析试剂溶剂化对 [BA⊂β-CD] 分子复合物形成的 Gibbs 能量变化的贡献。β-CD与BA相互作用能及[BA⊂β-CD]配合物结构的量子化学计算，以及β-CD与BA在真空和水、甲醇和二甲亚砜介质中相
• Inclusion Complexes of ß-Cyclodextrin and Its Silyl Derivative with Some Pharmacologically Important Aromatic Monocarboxylic Acids
  作者：M. K. Grachev、I. A. Senyushkina、G. I. Kurochkina、K. A. Lysenko、L. K. Vasyanina、E. E. Nifant’ev

  DOI：10.1134/s1070428010100118

  日期：2010.10

  Stable host-guest complexes of a-cyclodextrin and its silyl derivative with some aromatic monocarboxylic acids of pharmacological interest were prepared. The structure of the a-cyclodextrin complex with nicotinic acid was studied by X-ray diffraction.