| 125495-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 125495-83-2
• 化学式: C₈H₈O₃*C₄₂H₇₀O₃₅
• 分子量: 1287.15
• InChiKey: KDOUAZPCBUGFKY-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.02
• 重原子数：
  88.0
• 可旋转键数：
  9.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  600.58
• 氢给体数：
  22.0
• 氢受体数：
  38.0

反应信息

• 作为产物：
  描述：

  香草醛 、 β-环糊精 以 aq. buffer 为溶剂， 生成
  参考文献：
  名称：

  香兰素的自聚集和环糊精络合的DOSY-NMR和拉曼研究

  摘要：

  香兰素（4-羟基-3-甲氧基苯甲醛）是一种在水中溶解度有限的酚醛。在这项工作中，我们使用核磁共振（NMR）和振动光谱研究了它的自聚集以及与β-环糊精的络合平衡。尤其是，扩散有序NMR（DOSY）测量可检测由聚集/夹杂现象引起的扩散变化，从而可以可靠地估算这些过程的平衡常数，而拉曼光谱则可用于进一步表征香兰素自身结构的某些结构细节。聚集体和包合物。尽管发现香兰素在水中的自缔合常数很低（K a〜10），在所研究的浓度范围（3–65 mM）内，二聚体种类不可忽略；另一方面，通过DOSY测量，在不同浓度（2–12 mM）的β-环糊精水溶液中未检测到β-环糊精自聚集体的形成。最后，通过假设仅存在单体1：1香兰素/β-CD复合物，通过DOSY技术在狭窄的浓度范围（2-15 mM）中测量，香兰素与β-环糊精的结合约为数量级更高（的ķ ç〜90）比自聚集。然而，发现该络合物的平衡常数值受主体和客体系统分析浓度的显着影响，因此表明K

  DOI：

  10.1021/jp504406j

文献信息

• Spectroscopic study on the inclusion complexes of β-cyclodextrin with selected metabolites of catecholamines
  作者：Anna Korytkowska-Wałach、Beata Dubrawska、Monika Śmiga-Matuszowicz、Tadeusz Bieg

  DOI：10.1016/j.molstruc.2016.08.010

  日期：2017.1

  two possibilities of complexed molecule arrangement into β-cyclodextrin interior. The values of determined association constants are in good agreement with postulated geometry of the complexes. Value of association constant determined for inclusion complexes of β-cyclodextrin with homovanillic acid an vanillin indicates the strongest binding of molecules among investigated complexes, so it was finally

  摘要 使用核磁共振波谱研究了β-环糊精(β-CD) 与儿茶酚胺代谢物即香草扁桃酸(VMA)、高香草酸(HVA) 和香草醛(VA) 之间形成的包合物。由于这些化合物对诊断交感肾上腺系统肿瘤的重要性，含有 β-CD 部分的水凝胶用于增强从水溶液中捕获儿茶酚胺的代谢物是我们感兴趣的领域。β-CD 与 VMA、HVA 和 VA 的复合物的化学计量和缔合常数分别通过使用连续变化和 1 H NMR 滴定方法确定。根据所使用的参考方法指出了显着差异。在本研究中 3-(trimethylsilyl)propionic-2,2,3 的水溶液，使用 3-d4 酸钠盐作为外参，以避免测定缔合常数时出现错误。β-CD 与 VA 和 HVA 分子形成最稳定的复合物，而 VMA/β-CD 复合物的结合常数最小值被确定。二维旋转框架 Overhauser 效应光谱 (2D ROESY) 允许建立关于形成的复合物的分子结构的明确信息。后者的几何形状是基于
• Spectral and Molecular Modeling Studies on Hydroxybenzaldehydes with Native and Modified Cyclodextrins
  作者：M. Jude Jenita、T. Mohandass、N. Rajendiran

  DOI：10.1007/s10895-013-1340-5

  日期：2014.5

  The inclusion complexation of 2-hydroxy-3-methoxybenzaldehyde (2HMB), 4-hydroxy-3-methoxybenzaldehyde (4HMB), 3,4-dimethoxybenzaldehyde (DMB) and 4-hydroxy-3,5-dimethoxybenzaldehyde (HDMB) with α-CD, β-CD, HP-α-CD and HP-β-CD were carried out by UV-Visible, steady-state and time-resolved fluorescence and PM3 methods. All the benzaldehydes shows dual fluorescence in aqueous and CD mediums and 1:1 inclusion complexes were formed with CDs. PM3 geometry optimizations results indicate that the HDMB/CD complex is significantly more favorable than the other complexes. The negative enthalpy changes suggest that the inclusion complexation processes are spontaneous. The geometry of the most stable complex shows that methoxy/OH group of HMBs is entrapped in the less polar CD cavities, while the aldehyde group present in the upper part of the CDs cavities.

  2-羟基-3-甲氧基苯甲醛（2HMB）、4-羟基-3-甲氧基苯甲醛（4HMB）、3,4-二甲氧基苯甲醛（DMB）和4-羟基-3,5-二甲氧基苯甲醛（HDMB）与α-的包合络合CD、β-CD、HP-α-CD 和 HP-β-CD 通过紫外-可见、稳态和时间分辨荧光和 PM3 方法进行。所有苯甲醛在水介质和 CD 介质中均显示出双荧光，并且与 CD 形成 1:1 包合物。 PM3 几何优化结果表明 HDMB/CD 复合物明显优于其他复合物。负的焓变表明包合络合过程是自发的。最稳定复合物的几何形状表明，HMB 的甲氧基/OH 基团被捕获在极性较小的 CD 空腔中，而醛基存在于 CD 空腔的上部。
• Solid Inclusion Complexes of Vanillin with Cyclodextrins: Their Formation, Characterization, and High-Temperature Stability
  作者：Fatma Kayaci、Tamer Uyar

  DOI：10.1021/jf202915c

  日期：2011.11.9

  This study reports the formation of solid vanillin/cyclodextrin inclusion complexes (vanillin/CD ICs) with the aim to enhance the thermal stability and sustained release of vanillin by inclusion complexation. The solid vanillin/CD ICs with three types of CDs (alpha-CD, beta-CD, and gamma-CD) were prepared using the freeze-drying method; in addition, a coprecipitation method was also used in the case of gamma-CD. The presence of vanillin in CD ICs was confirmed by FTIR and (1)H NMR studies. Moreover, (1)H NMR study elucidated that the complexation stoichiometry for both vanillin/beta-CD IC and vanillin/gamma-CD IC was a 1:1 molar ratio, whereas it was 0.625:1 for vanillin/alpha-CD IC. XRD studies have shown channel-type arrangement for CD molecules, and no diffraction peak for free vanillin was observed for vanillin/beta-CD IC and vanillin/gamma-CD IC, indicating that complete inclusion complexation was successfully achieved for these CD ICs. In the case of vanillin/alpha-CD IC, the sample was mostly amorphous and some uncomplexed vanillin was present, suggesting that alpha CD was not very effective for complexation with vanillin compared to beta-CD and gamma-CD. Furthermore, DSC studies for vanillin/beta-CD IC and vanillin/gamma-CD IC have shown no melting point for vanillin, elucidating the true complex formation, whereas a melting point for vanillin was recorded for vanillin/alpha-CD IC, confirming the presence of some uncomplexed vanillin in this sample. TGA thermograms indicated that thermal evaporation/degradation of vanillin occurred over a much higher temperature range (150-300 degrees C) for vanillin/CD ICs samples when compared to pure vanillin (80-200 degrees C) or vanillin/CD physical mixtures, signifying that the thermal stability of vanillin was increased due to the inclusion complexation with CDs. Moreover, headspace GC-MS analyses indicated that the release of vanillin was sustained at higher temperatures in the case of vanillin/CD ICs due to the inclusion complexation when compared to vanillin/CD physical mixtures. The amount of vanillin released with increasing temperature was lowest for vanillin/gamma-CD IC and highest for vanillin/alpha-CD IC, suggesting that the strength of interaction between vanillin and the CD cavity was in the order gamma-CD > beta-CD > alpha-CD for solid vanillin/CD ICs.