per-O-valeryl-β-cyclodextrin | 121783-11-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: per-O-valeryl-β-cyclodextrin
• 英文别名: tri-O-valeryl-β-cyclodextrin；[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36S,37R,38S,39R,40S,41R,42S,43R,44S,45R,46S,47R,48S,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradeca(pentanoyloxy)-10,15,20,25,30,35-hexakis(pentanoyloxymethyl)-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]nonatetracontan-5-yl]methyl pentanoate
• CAS: 121783-11-7
• 化学式: C₁₄₇H₂₃₈O₅₆
• 分子量: 2901.47
• InChiKey: ABHUFUIOWKJYKZ-SMOFKLLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.8
• 重原子数：
  203
• 可旋转键数：
  112
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  682
• 氢给体数：
  0
• 氢受体数：
  56

反应信息

• 作为反应物：
  描述：

  per-O-valeryl-β-cyclodextrin 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 生成 Pentanoic acid (2R,3R,4S,5S)-3-hydroxy-5-pentanoyloxy-2-pentanoyloxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  还原裂解法表征环麦芽六糖和庚糖衍生物

  摘要：

  摘要：通过还原裂解方法研究了带有烷基，酰基和氨基甲酰基取代基的环麦芽六糖和庚糖衍生物的取代方式。用三乙基硅烷和三甲基甲硅烷基三氟甲磺酸酯处理改性的环麦芽六糖或庚二酮酶，得到相应的1,5-和1,4-脱水葡萄糖醇衍生物，将其乙酰化，或在乙酰基衍生物的情况下，将三氟乙酰基化，并通过glc-ms分析可以检测到烷基化化合物，烷基化不足或烷基化形成的微量产物或异构体组分。观察到酰氧基部分还原为烷氧基和酰基取代基的裂解。氨基甲酰基取代基在还原裂解的条件下是稳定的。

  DOI：

  10.1016/0008-6215(89)80003-5
• 作为产物：
  描述：

  戊酸酐 、 β-环糊精 在 碘 作用下， 反应 24.0h， 以91%的产率得到per-O-valeryl-β-cyclodextrin
  参考文献：
  名称：

  A Simple and Convenient Per-O-acylation of Cyclodextrins Catalyzed by Molecular Iodine

  摘要：

  在无溶剂条件下，通过用羧酸酐对环糊精的所有羟基进行碘催化酰化，以良好至高产率制备了具有不同烷基链的全O-酰化环糊精。

  DOI：

  10.1055/s-0030-1258163

文献信息

• Characterization of Peracylated .BETA.-Cyclodextrins with Different Chain Lengths as a Novel Sustained Release Carrier for Water-Soluble Drugs.
  作者：Fumitoshi HIRAYAMA、Masayuki YAMANAKA、Takashi HORIKAWA、Kaneto UEKAMA

  DOI：10.1248/cpb.43.130

  日期：——

  A new series of peracylated β-cyclodextrins (β-CyDs) with different alkyl chains (acetyl-lauroyl) was prepared in high purity by acylating all hydroxyl groups of β-CyD using acid anhydrides in pyridine, and their physicochemical properties of solubility, hydrolsis and release and interaction capacity were evaluated. The solublity of peracylated β-CyDs in water decreased with lengthening alkyl chain, whereas that in ethanol/water increased with increase in ethanol concentration, but tended to decrease at higher ethanol concentration. The solubility parameter of peracylated β-CyDs was determined by analyzing the peak-solubility phenomenon by a modified Hildebrand equation. The alkaline hydrolysis rate of peracylated β-CyDs decreased with lengthening alkyl chain, and was about 4-fold faster than that of the corresponding fatty acid ethyl esters. The interaction of perbutanoyl-β-CyD (TB-β-CyD) with a water-soluble drug, molsidomine, in the solid state was investigated by differential scanning calorimetry (DSC). The analysis of DSC curves suggested that molsidomine and TB-β-CyD form a binary solid dispersion with a 2 : 1 (drug : TB-β-CyD) molar ratio. The rate of drug release was markedly retarded by the combination with peracylated β-CyDs in the increasing order of the hydrophobicity of host molecules.

  一种新的醇酰化β-环糊精（β-CyD）系列，采用不同的烷基链（醋酸-月桂酰基）在高纯度下制备，通过在吡啶中使用酸酐对β-CyD的所有羟基进行酰化，并评估了其在溶解度、水解、释放和相互作用能力方面的物理化学性质。醇酰化β-CyDs在水中的溶解度随着烷基链的延长而降低，而在乙醇/水中的溶解度则随着乙醇浓度的增加而增加，但在较高乙醇浓度下则趋于降低。通过分析峰值溶解现象，采用改进的希尔德布兰德方程确定了醇酰化β-CyDs的溶解度参数。醇酰化β-CyDs的碱性水解速率随着烷基链的延长而降低，且约为相应脂肪酸乙酯的4倍。通过差示扫描量热法（DSC）研究了铂丁酰-β-CyD（TB-β-CyD）与一种水溶性药物莫沙吡啶在固态下的相互作用。DSC曲线的分析表明，莫沙吡啶与TB-β-CyD形成一种2:1（药物:TB-β-CyD）摩尔比的二元固体分散体。药物释放速率因与醇酰化β-CyDs的结合而显著减缓，且减缓程度按宿主分子的疏水性递增排列。
• Peracylated β-Cyclodextrins as Novel Sustained-release Carriers for a Water-soluble Drug, Molsidomine
  作者：Kaneto Uekama、Takashi Horikawa、Masayuki Yamanaka、Fumitoshi Hirayama

  DOI：10.1111/j.2042-7158.1994.tb03889.x

  日期：2011.4.12

  Peracylated β-cyclodextrins with different alkyl chains (acetyl-octanoyl) were prepared by acylating all hydroxyl groups of β-cyclodextrin (β-CyD), and their physical properties were evaluated. These hydrophobic β-CyDs decreased the release rate of molsidomine, a peripheral vasodilator, in proportion to the lengthening of alkyl chain and suppressed a peak plasma level of molsidomine following oral administration of peracylated β-CyD complexes to dogs. Among the peracylated β-CyDs tested, perbutanoyl-β-CyD maintained sufficient plasma drug levels for a long period of time, while other peracylated β-CyDs having shorter or longer chains were inappropriate to control the in-vivo release behaviour of molsidomine. The prominent retarding effect of perbutanoyl-β-CyD was ascribable to the appropriate mucoadhesive property and hydrophobicity, compared with other peracylated β-CyDs. The present results suggest that perbutanoyl-β-CyD is particularly useful in modifying the release rate of water-soluble drugs as a novel slow-release carrier.

  通过酰化β-环糊精（β-CyD）的所有羟基，制备了具有不同烷基链（乙酰-辛酰）的过酰化β-环糊精，并评估了它们的物理性质。这些疏水性β-CyD随着烷基链的延长而降低了周围血管扩张剂莫西多明的释放速率，并通过口服给犬类的过酰化β-CyD复合物抑制了莫西多明的峰值血浆水平。在测试的过酰化β-CyD中，过丁酰-β-CyD维持了足够长时间的血药平衡，而其他烷基链较短或较长的过酰化β-CyD则不适合控制莫西多明的体内释放行为。与其他过酰化β-CyD相比，过丁酰-β-CyD的显著减缓效果可归因于其适当的黏附性和疏水性。本研究结果表明，过丁酰-β-CyD作为一种新型缓释载体，特别适用于调节水溶性药物的释放速率。

• Characterization of cyclomalto-hexaose and -heptaose derivatives by the reductive-cleavage method
  作者：Petra Mischnick-Lübbecke、Ralph Krebber

  DOI：10.1016/0008-6215(89)80003-5

  日期：1989.4

  The substitution patterns of cyclomalto-hexaose and -heptaose derivatives carrying alkyl, acyl, and carbamoyl substituents have been investigated by the reductive-cleavage method. The modified cyclomalto-hexaoses or -heptaoses were treated with triethylsilane and trimethylsilyl trifluoromethanesulfonate to give the corresponding 1,5- and 1,4-anhydroglucitol derivatives that were acetylated or, in the

  摘要：通过还原裂解方法研究了带有烷基，酰基和氨基甲酰基取代基的环麦芽六糖和庚糖衍生物的取代方式。用三乙基硅烷和三甲基甲硅烷基三氟甲磺酸酯处理改性的环麦芽六糖或庚二酮酶，得到相应的1,5-和1,4-脱水葡萄糖醇衍生物，将其乙酰化，或在乙酰基衍生物的情况下，将三氟乙酰基化，并通过glc-ms分析可以检测到烷基化化合物，烷基化不足或烷基化形成的微量产物或异构体组分。观察到酰氧基部分还原为烷氧基和酰基取代基的裂解。氨基甲酰基取代基在还原裂解的条件下是稳定的。
• A Simple and Convenient Per-O-acylation of Cyclodextrins Catalyzed by Molecular Iodine
  作者：Tsugio Kitamura、Yasuhiro Ide、Yuji Hori、Soichi Kobayashi、Md. Hossain

  DOI：10.1055/s-0030-1258163

  日期：2010.9

  Per-O-acylated cyclodextrins with different alkyl chains were prepared in good to high yields by iodine-catalyzed acylation of all hydroxy groups of cyclodextrins with carboxylic anhydrides under solvent-free conditions.

  在无溶剂条件下，通过用羧酸酐对环糊精的所有羟基进行碘催化酰化，以良好至高产率制备了具有不同烷基链的全O-酰化环糊精。