methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate | 72500-11-9

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate
• 英文别名: 3-methoxy-4-O-β-D-glucopyranosyl methyl benzoate；3-methoxyl-4-O-β-D-glucopyranosyloxybenzoic acid methyl ester；methyl 4-(β-D-glucopyranosyloxy)-3-methoxybenzoate；methyl vanillate 4-O-beta-D-glucoside；4-O-β-D-glucopyranosylvanillic acid methyl ester；Methyl vanillate glucoside；methyl 3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• CAS: 72500-11-9
• 化学式: C₁₅H₂₀O₉
• 分子量: 344.318
• InChiKey: INSAQPSCUXYJAY-ZHZXCYKASA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• 储存条件：
  室温

制备方法与用途

甲基愈创木酯葡萄糖苷是从Lycium schweinfurthii中分离得到的一种次级代谢产物。

反应信息

• 作为反应物：
  描述：

  methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate 在 4-二甲氨基吡啶 、 sodium hydride 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成
  参考文献：
  名称：

  寡聚4-（乙醇酰氧基）苯甲酸酯大环糖苷的合成

  摘要：

  首次合成了Clemoarmanoside A和Clemahexapetoside A，这两种新型的4-（糖氧基氧基）苯甲酸酯的新型环状二聚体，其中含有不寻常的d-吡喃戊糖作为糖单元之一。方便的合成方法适用于对称三聚体，四聚体和五聚体同源物的组装。合成澄清了天然产物报道的NMR数据的差异。Clemahexapetoside A的X射线衍射分析表明，它采用了扶手椅构型，两个碳水化合物环分别为手臂，两个芳香环分别为椅背和座位。

  DOI：

  10.1021/jo200440r
• 作为产物：
  描述：

  香草酸甲酯 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate
  参考文献：
  名称：

  寡聚4-（乙醇酰氧基）苯甲酸酯大环糖苷的合成

  摘要：

  首次合成了Clemoarmanoside A和Clemahexapetoside A，这两种新型的4-（糖氧基氧基）苯甲酸酯的新型环状二聚体，其中含有不寻常的d-吡喃戊糖作为糖单元之一。方便的合成方法适用于对称三聚体，四聚体和五聚体同源物的组装。合成澄清了天然产物报道的NMR数据的差异。Clemahexapetoside A的X射线衍射分析表明，它采用了扶手椅构型，两个碳水化合物环分别为手臂，两个芳香环分别为椅背和座位。

  DOI：

  10.1021/jo200440r

文献信息

• GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS
  申请人：PepsiCo, Inc.

  公开号：US20180020708A1

  公开（公告）日：2018-01-25

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R 1 , R 2 , R 3 , and R 4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了包含具有如下式I的结构的化合物的新型甜味剂组合物： 其中R1、R2、R3和R4如本文所述。还提供了通过向产品添加式I的化合物来调节产品的甜味特性的方法，例如饮料产品或食品产品。例如，本文描述的化合物可添加以增加富含甜味剂的饮料的整体甜度；减少高效甜味剂（如甜菊糖A）的甜味起始时间；减少高效甜味剂的苦味、金属味和甘草味等异味；并改善甜味产品的甜味质量。
• Glucosyringic acid analogs as sweetness profile modifiers
  申请人：PepsiCo, Inc.

  公开号：US10966447B2

  公开（公告）日：2021-04-06

  The present disclosure provides novel sweetener compositions comprising a compound having a structure according to Formula I: wherein R1, R2, R3, and R4 are described herein. Also provided are methods of modulating sweetness profile of a product by adding a compound of Formula I to the product, such as a beverage product or a food product. For example, the compound described herein can be added to increase the overall sweetness of a nutritive sweetener sweetened beverages; decrease the sweetness time-of-onset for high potency sweeteners such as rebaudioside A; decreasing bitter, metallic and licorice off-notes of high potency sweeteners; and improve the sweet quality of sweetened products.

  本公开提供了新型甜味剂组合物，该组合物包含具有根据式 I 所述结构的化合物：其中 R1、R2、R3 和 R4 已在本文中描述。 还提供了通过向饮料产品或食品等产品中添加式 I 化合物来调节产品甜度曲线的方法。 例如，添加本文所述的化合物可增加营养型甜味剂甜饮料的总体甜度；减少高活性甜味剂（如雷公藤甙 A）的甜味起效时间；减少高活性甜味剂的苦味、金属味和甘草味；以及改善甜味产品的甜味质量。
• Molecular Interactions between Barley and Oat β-Glucans and Phenolic Derivatives
  作者：Henrik Toft Simonsen、Mette S. Nielsen、Niels J. Christensen、Ulla Christensen、Thomas V. La Cour、Mohammed Saddik Motawia、Birthe P. M. Jespersen、Søren B. Engelsen、Birger Lindberg Møller

  DOI：10.1021/jf802057v

  日期：2009.3.11

  Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available beta-glucan preparations, Glucagel and PromOat, from barley and oats. The two beta-glucan products showed very similar binding properties. It was demonstrated that the two beta-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the beta-glucans. When the barley beta-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
• Total synthesis of macrocyclic glycosides, clemochinenosides A and B, and berchemolide, by fluorous mixture synthesis
  作者：Masaru Kojima、Yutaka Nakamura、Shun Ito、Seiji Takeuchi

  DOI：10.1016/j.tetlet.2009.08.068

  日期：2009.11

  The total synthesis of clemochinenoside A and the first total syntheses of clemochinenoside B and berchemolide were achieved simultaneously via macrocyclization of 4-O-(4-O-(F13)benzyl-beta-D-glucopyranosyl)syringic acid with 4-O-(4-O-(F17)-benzyl-beta-D-glucopyranosyl)vanillic acid by a fluorous mixture synthetic method. The spectroscopic data of the synthetic products were identical with those of the natural products, although the optical rotation of clemochinenoside A differed from the published values in sign and magnitude. (C) 2009 Elsevier Ltd. All rights reserved.
• A new glucoside with a potent α-glucosidase inhibitory activity from <i>Lycium schweinfurthii</i>
  作者：Ahmed Elbermawi、Ahmed F. Halim、El-Sayed S. Mansour、Kadria F. Ahmad、Ahmed Ashour、Yhiya Amen、Kuniyoshi Shimizu

  DOI：10.1080/14786419.2019.1616730

  日期：2021.3.19

  A new glucoside, 3-methoxy-4-O-beta-D-glucopyranosyl-methyl benzoate, has been isolated from Lycium schweinfurthii along with five known compounds through bioactivity guided fractionation of the total plant methanolic extract towards alpha-glucosidase inhibitory activity. All the isolated compounds were tested for their inhibitory effect on alpha-glucosidase enzyme. As a result, four of them showed a potent inhibitory activity and thus constitute a therapeutic approach to decrease postprandial hyperglycemia in diabetic patients.[GRAPHICS].