2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone | 1429764-06-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone
• 英文别名: 2-(2,3,4,6-tetra-O-acetyl-beta-d-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenon；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-(4-methoxy-3-phenylmethoxyphenyl)-2-oxoethoxy]oxan-2-yl]methyl acetate
• CAS: 1429764-06-6
• 化学式: C₃₀H₃₄O₁₃
• 分子量: 602.592
• InChiKey: YJEBRNRRMDTPSE-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 在 盐酸 、 三乙基硅烷 、 palladium on carbon 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside

  摘要：

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.100
• 作为产物：
  描述：

  3-Hydroxy-4-methoxy-α-chloroacetophenone 在 sodium hydride 、 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone
  参考文献：
  名称：

  First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside

  摘要：

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.100

文献信息

• Characterization of Kinetic and Thermodynamic Parameters of Cyanidin-3-glucoside Methyl and Glucuronyl Metabolite Conjugates.
  作者：Luís Cruz、Nuno Basílio、Nuno Mateus、Fernando Pina、Victor de Freitas

  DOI：10.1021/jp511537e

  日期：2015.2.5

  The determination of rate and equilibrium constants of anthocyanin metabolites with in vivo occurrence, cyanidin-4'-O-methyl-3-glucoside (Cy4'Me3glc) and cyanidin-7-O-glucuronyl-3-glucoside (Cy7Gluc3glc), was carried out for the first time by means of direct and reverse pH jumps. The thermodynamics and kinetics of these compounds are similar to the anthocyanin monoglucosides in particular for the analogous cyanidin-3-glucoside (Cy3glc) and peonidin-3-glucoside (Peo3glc). The rate and equilibrium constants of metabolites were also compared with malvin (malvidin 3,5-diglucoside) and with a bioinspired compound 3',4'-dihydroxy-7-O-glucopyranosyloxyflavylium (DGF). In Cy4'Me3glc and Cy7Gluc3glc the rate of hydration for a fixed pH value is slower than in DGF and the dominant species at moderately acidic solutions is the hemiketal. Oppositely, in DGF trans-chalcone is the dominant species at moderately acidic solutions.