(2S)-cyclo-Dopa 5-O-glucoside | 71242-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-cyclo-Dopa 5-O-glucoside
• 英文别名: cyclodopa glucoside；cyclo-dopa 5-O-glucoside；(2S)-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydro-1H-indole-2-carboxylic acid
• CAS: 71242-23-4
• 化学式: C₁₅H₁₉NO₉
• 分子量: 357.317
• InChiKey: PXMFPPFHRQZIHO-OLCQZNMOSA-N

物化性质

• 沸点：
  745.3±60.0 °C(Predicted)
• 密度：
  1.682±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-cyclo-Dopa 5-O-glucoside 在 甲酸 作用下， 反应 2160.0h， 生成 5-(β-D-glucopyranosyloxy)-6-hydroxyindol-2-carboxylic acid 、 N-formyl cyclodopa glucoside
  参考文献：
  名称：

  Cyclodopa葡糖苷（=（2小号）-5-（β-d-glocopyranosyloxy）-6- hydroxyindoline -2-羧酸）和它的在红甜菜发生（甜菜变种杨梅L.）

  摘要：

  由甜菜碱（2a）经碱交换反应制备环多巴葡糖苷（＝（2S）-5-（β-D-吡喃葡萄糖基氧基）-6-羟基二氢吲哚-2-羧酸；1a）。描述了其纯化和物理性质。该化合物在稀HCOOH溶液中被N-甲酰化。甜菜汁中含有大量的环多巴葡糖苷，相对于甜菜素含量为0.07至1.9 mmol / kg或12至46％。游离环多巴葡萄糖苷的出现支持了其作为甜菜碱生物合成中间体的作用。

  DOI：

  10.1002/hlca.19840670520
• 作为产物：
  描述：

  betanidin 5-O-β-D-glucoside 在 盐酸 作用下， 生成 Betalaminsaeure 、 (2S)-cyclo-Dopa 5-O-glucoside
  参考文献：
  名称：

  Intramolecular stabilization of acylated betacyanins

  摘要：

  Racemization and stability of the betacyanins, betanin (betanidin 5-O-glucoside) and amaranthin (betanidin 5-O-glucuronosylglucoside), under acidic conditions were compared with those of the corresponding feruloyl derivatives, lampranthin II and celosianin II. Both acylbetacyanins showed a reduced racemization velocity and celosianin II in addition an enhanced stability, possibly caused by intramolecular association between the betanidin and the feruloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00047-8

文献信息

• Intramolecular stabilization of acylated betacyanins
  作者：Willibald Schliemann、Dieter Strack

  DOI：10.1016/s0031-9422(98)00047-8

  日期：1998.9

  Racemization and stability of the betacyanins, betanin (betanidin 5-O-glucoside) and amaranthin (betanidin 5-O-glucuronosylglucoside), under acidic conditions were compared with those of the corresponding feruloyl derivatives, lampranthin II and celosianin II. Both acylbetacyanins showed a reduced racemization velocity and celosianin II in addition an enhanced stability, possibly caused by intramolecular association between the betanidin and the feruloyl moieties. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Cyclodopa glucoside ( = (2S)-5-(?-D-glocopyranosyloxy)-6-hydroxyindoline-2-carboxylic acid) and its occurrence in red beet (beta vulgaris var.rubra L.)
  作者：Hugo Wyler、Ursula Meuer、Jacques Bauer、Luisa Stravs-Mombelli

  DOI：10.1002/hlca.19840670520

  日期：1984.8.8

  Cyclodopa glucoside ( = (2S)-5-(β-D-glucopyranosyloxy)-6-hydroxyindoline-2-carboxylicacid; 1a) is prepared from betainin (2a) via a base exchange reaction. Its purification and physical properties are described. The compound is N-formylated in dilute HCOOH solution. Cyclodopa glucoside is contained in considerable amount in redbeet juice varying from 0.07 to 1.9 mmol/kg or from 12 to 46% relative to

  由甜菜碱（2a）经碱交换反应制备环多巴葡糖苷（＝（2S）-5-（β-D-吡喃葡萄糖基氧基）-6-羟基二氢吲哚-2-羧酸；1a）。描述了其纯化和物理性质。该化合物在稀HCOOH溶液中被N-甲酰化。甜菜汁中含有大量的环多巴葡糖苷，相对于甜菜素含量为0.07至1.9 mmol / kg或12至46％。游离环多巴葡萄糖苷的出现支持了其作为甜菜碱生物合成中间体的作用。