4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)vanillic acid methyl ester | 72500-10-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)vanillic acid methyl ester
• 英文别名: methyl 3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoate；(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-methoxy-4-(methoxycarbonyl)phenoxy)tetrahydro-2H-3,4,5-triyl triacetate；3-methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoic acid methyl ester；3-Methoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzoesaeure-methylester；methyl 3-methoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybenzoate
• CAS: 72500-10-8
• 化学式: C₂₃H₂₈O₁₃
• 分子量: 512.468
• InChiKey: YWYHUPWOVGIEBB-ZFVIQDPVSA-N

物化性质

• 熔点：
  144-145 °C
• 沸点：
  575.1±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)vanillic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 香草酸-4-Β-D-葡萄糖苷
  参考文献：
  名称：

  Berchemolide，一种来自Berchemia racemosa的新型二聚香草酸葡糖苷。

  摘要：

  从总的Berchemia racemosa Sieb的茎中分离出一种名为berchemolide的新苯酚糖苷，以及（+）-儿茶素和（-）-epicatechin（作为乙酸盐）。et Zucc。（鼠李科）。基于光谱和化学研究确定了具有二聚二内酯结构和22元环的berchemolide的结构。通过MNDO（修正的对双原子重叠的忽略）来计算berchemolide的构象。

  DOI：

  10.1248/cpb.40.851
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)vanillic acid methyl ester
  参考文献：
  名称：

  GLUCOSYRINGIC ACID ANALOGS AS SWEETNESS PROFILE MODIFIERS

  摘要：

  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。

  公开号：

  US20180020708A1

文献信息

• Revisit of the phenol O-glycosylation with glycosyl imidates, BF3·OEt2 is a better catalyst than TMSOTf
  作者：Yali Li、Huaping Mo、Gaoyan Lian、Biao Yu

  DOI：10.1016/j.carres.2012.09.025

  日期：2012.12

  With BF(3)·OEt(2) as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent

  以BF（3）·OEt（2）为催化剂，苯酚与带有2-O-参与基团的糖基三氯乙酰基亚氨酸盐（或N-苯基三氟乙酰基亚氨酸盐）的糖基化反应通常会产生所需的1,2-反式-O-糖苷极佳的收率，而不会形成1,2-顺式端基异构体。然而，以TMSOTf为催化剂，相应的酚O-糖基化的结果高度依赖于酚的亲核性。苯酚的亲核性越少，生成的1，2-顺式-O-糖苷含量越高，副产物就越多。在所有这些酚O-糖基化反应中，发现1,2-原酸酯是低温（<-70°C）的主要产物，在较高温度下转化为最终产物。BF（3）·OEt（2）是促进1转化的有效催化剂 将2-原酸酯转化为相应的1，2-反式-O-糖苷。然而，在TMSOTf存在下，1,2-原酸酯可被转化为三氟甲磺酸二恶唑鎓和三氟甲磺酸糖基酯，这些中间体可能与糖基氧碳鎓相关物种处于平衡状态，最终形成α/β-O-的最终混合物。苷和副产物。
• Synthesis of Oligomeric 4-(Glycosyloxy)benzoate Macrocyclic Glycosides
  作者：Yali Li、Jiansong Sun、Yanqing Gong、Biao Yu

  DOI：10.1021/jo200440r

  日期：2011.5.20

  Clemoarmanoside A and Clemahexapetoside A, two novel cyclic dimers of 4-(glycosyloxy)benzoates containing the unusual d-allopyranose as one of the sugar units, were synthesized for the first time. The convenient synthetic approach was adapted to the assembly of the symmetrical trimeric, tetrameric, and pentameric congeners. The synthesis clarified the discrepancy in the NMR data reported for the natural

  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。
• 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.
• King et al., Journal of the Chemical Society, 1955, p. 4206,4213
  作者：King et al.

  DOI：——

  日期：——