丁基葡糖苷 | 5391-18-4

• 物质功能分类: 生物化工 - 生化试剂
• 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: 丁基葡糖苷
• 中文别名: 丁基-beta-d-吡喃葡萄糖苷
• 英文名称: n-butyl β-D-glucopyranoside
• 英文别名: O-n-butyl β-D-glucopyranoside；Butyl beta-D-glucopyranoside；(2R,3R,4S,5S,6R)-2-butoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 5391-18-4
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: BZANQLIRVMZFOS-HOTMZDKISA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 储存条件：
  储存温度应保持在2-8°C，并需密封保存。

反应信息

• 作为反应物：
  描述：

  丁基葡糖苷 在 水 作用下， 以 水 为溶剂， 反应 168.0h， 生成 戊基BETA-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1
• 作为产物：
  描述：

  戊基BETA-D-吡喃葡萄糖苷 在 almond meal 作用下， 以 水 为溶剂， 反应 336.0h， 生成 丁基葡糖苷
  参考文献：
  名称：

  Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

  摘要：

  An array of ten beta-D-glueopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl beta-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl beta-D-glucoside was found to have significant surface activity as well.

  DOI：

  10.1016/s1872-2067(11)60333-1

文献信息

• Kinetics and mechanism of the acid-catalysed butanolysis of 1,6-anhydro-β-d-glucopyranose
  作者：Adrie J.J. Straatho、Johannes M. Vrolijk、Herman van Bekkum、Antonius P.G. Kieboom

  DOI：10.1016/0008-6215(88)80014-4

  日期：1988.12

  Abstract The sulfuric acid-catalysed reaction of 1,6-anhydro-β- d -glucopyranose in 1-butanol at 80° gave butyl α- and β- d -glucopyranoside as the sole products. The initial kinetic α/β ratio was 1.5, and the final α/β ratio upon equilibration was 2.7. The four pseudo-first-order reaction rate constants involved have been determined. Conformational studies showed that the reaction probably proceeds

  摘要1，6-脱水-β-d-吡喃葡萄糖在1-丁醇中于80°C硫酸催化反应，可得丁基α-和β-d-吡喃葡萄糖苷为唯一产物。初始动力学α/β比为1.5，平衡时最终α/β比为2.7。已经确定了所涉及的四个伪一级反应速率常数。构象研究表明，该反应可能通过1，6-脱水-β-d-吡喃葡萄糖与1 4 H 3样碳氧化合物的1 C 4-B o，3相互转化而进行。
• A new phenolic metabolite, involutone, isolated from the mushroom <i>Paxillus involutus</i>
  作者：Róza Antkowiak、Wieslaw Z Antkowiak、Izabela Banczyk、Lucyna Mikolajczyk

  DOI：10.1139/v02-194

  日期：2003.1.1

  as well as methyl, ethyl, or n-butyl-β-D-glucopyranosides, and methyl, ethyl, or n-butyl linoleates, depending in both cases on the alcohol used in the extraction, were also isolated in a pure state from the mushroom.Key words: Paxillus involutus, Brown Roll-rim, metabolite isolation, structure study, quaternary hydroxycyclopentanedione, NMR of mushroom pigments, glucosides and linoleates, enzymic glucosylation

  一种新的光学活性代谢物 involutone，在新鲜收集的 Paxillus involutus 的甲醇、乙醇或正丁醇提取物中被发现。根据光谱和化学性质证明该化合物的结构为 5-(3,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-2-hydroxy-4-cyclopenten-1,3-dione内卷酮及其四乙酰基衍生物。此外，许多已知结构的化合物，例如亚油酸和巴豆酸、甘露醇、麦角甾醇、内卷素，以及甲基、乙基或正丁基-β-D-吡喃葡萄糖苷，以及甲基、乙基或正丁基亚油酸酯，在这两种情况下都取决于提取中使用的酒精，也从蘑菇中以纯状态分离出来。 关键词： 渐开线芽孢杆菌，棕卷缘，代谢物分离，结构研究，季羟基环戊二酮，蘑菇色素的核磁共振，
• SnCl₄- and TiCl₄-Catalyzed Anomerization of Acylated <i>O</i>- and <i>S</i>-Glycosides: Analysis of Factors That Lead to Higher α:β Anomer Ratios and Reaction Rates
  作者：Wayne Pilgrim、Paul V. Murphy

  DOI：10.1021/jo101090f

  日期：2010.10.15

  glucuronic acid or galacturonic acid derivatives were ∼10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and α:β ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron

  讨论了影响SnCl 4和TiCl 4催化的异构化反应速率和立体选择性的因素的定量，以及这如何影响α- O-和α- S-糖脂的合成。SnCl 4催化的18种底物的β- S-和β- O-糖苷的阴离子化反应遵循一级平衡动力学，得到k f + k r值，其中k f是正向反应的速率常数（β→ α）和k r是逆反应的速率常数（α→β）。比较k f + k r值表明，葡萄糖醛酸或半乳糖醛酸衍生物的反应比相关的葡萄糖苷和吡喃半乳糖苷对应物的反应快约10至3000倍，并且α：β比率通常也更高。由半乳糖配置的化合物产生的立体电子效应比相应的糖苷的高达快2倍。越来越多地释放电子的基团（包括保护基）的引入通常导致速率提高。S-糖苷的异构化速度始终快于相应的O-糖苷。与TiCl 4的反应通常比与SnCl 4的反应更快。端基异构体的比例取决于路易斯酸，路易斯酸的当量数，温度和底物。对于TiCl 4促进的反应，观察到O
• Cellulose conversion into alkylglycosides in the ionic liquid 1-butyl-3-methylimidazolium chloride
  作者：Igor A. Ignatyev、Pascal G. N. Mertens、Charlie Van Doorslaer、Koen Binnemans、Dirk E. de Vos

  DOI：10.1039/c0gc00192a

  日期：——

  The conversion of cellulose into alkylglycosides is carried out in the ionic liquid 1-butyl-3-methylimidazolium chloride in the presence of an acidic catalyst. Primary alcohols like n-butanol and n-octanol were used as alkylating reagents. The acidic resin Amberlyst 15DRY proved to be the optimum heterogeneous catalyst: it catalyzes the hydrolysis of the β(1→4) links in the cellulose polymeric chain

  纤维素向烷基糖苷的转化是在离子液体中进行的 1-丁基-3-甲基咪唑鎓氯化物 在酸性条件下 催化剂。 伯醇 喜欢 正丁醇 和 正辛醇用作烷基化试剂。酸性树脂Amberlyst 15DRY被证明是最佳的非均质材料催化剂：催化 水解 纤维素聚合物链中β（1→4）键的位置以及 烷基化 的 羟 团体 在C1的位置 葡萄糖中间的。纤维素在温和条件下完全转化；与...反应正丁醇，得到的产量 丁基吡喃葡萄糖苷 异构体为86％。
• POLYMER STABILIZER
  申请人：KIMURA Yoshikazu

  公开号：US20100179253A1

  公开（公告）日：2010-07-15

  A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n− 1 ) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: C n H 2n O n (1) (wherein, n represents an integer of 3 or more).

  一种聚合物稳定剂，包含以下烷氧基化合物：所述烷氧基化合物是通过将含有以下通式（1）中的一个甲酰基或羰基以及分子中（n-1）个羟基的化合物中的至少一个羟基进行烷氧基化而得到的化合物，其中烷基团含有1至12个碳原子：CnH2nOn（1）（其中，n代表3或以上的整数）。