3,4,5-trihydroxybenzoic-2,6-d2 acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-trihydroxybenzoic-2,6-d2 acid
• 英文别名: Gallic acid-d2；2,6-dideuterio-3,4,5-trihydroxybenzoic acid
• 化学式: C₇H₆O₅
• 分子量: 172.106
• InChiKey: LNTHITQWFMADLM-QDNHWIQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  没食子酸 在 nafion resin 、 重水 作用下， 反应 24.0h， 生成 3,4,5-trihydroxybenzoic-2,6-d2 acid
  参考文献：
  名称：

  The deuteriation of constituents in olive oil and red wine with Nafion, a polymer supported acid catalyst

  摘要：

  已经开发了一种用于去氘化大量含有酚和甲氧基取代基的芳香化合物的程序，使用了Nafion这一聚合物支持的酸催化剂。在这些条件下，对红酒和橄榄油中存在的一系列化合物进行了去氘化。该程序为同香草醇、同香草酸、香荚兰酸、香荚兰醛和香草醛的标记提供了一个简便的途径。该方法也适用于这些化合物的标记氚化。版权所有 © 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.524

文献信息

• A simple procedure for the deuteriation of phenols
  作者：Kellie L. Tuck、Hai-Wei Tan、Peter J. Hayball

  DOI：10.1002/1099-1344(200007)43:8<817::aid-jlcr366>3.0.co;2-e

  日期：2000.7

  A simple procedure for the deuteriation of a large range of phenols has been developed using Amberlyst 15, a polymer supported acid catalyst. A number of phenols present in olive oil have been successfully deuteriated. The aromatic protons of hydroxytyrosol are 100% exchanged under the conditions used. This method is applicable for the tritiation of phenols. Copyright © 2000 John Wiley & Sons, Ltd

  使用 Amberlyst 15（一种聚合物负载的酸催化剂）开发了一种用于对多种酚类进行氘化的简单程序。橄榄油中存在的许多酚类已被成功地氘化。在所使用的条件下，羟基酪醇的芳香质子是 100% 交换的。该方法适用于苯酚的氚化。版权所有 © 2000 John Wiley & Sons, Ltd.
• The deuteriation of constituents in olive oil and red wine with Nafion, a polymer supported acid catalyst
  作者：Kellie L. Tuck、Peter J. Hayball

  DOI：10.1002/jlcr.524

  日期：2001.12

  A procedure for the deuteriation of a large range of aromatic compounds with phenolic and methoxy substituents has been developed using Nafion, a polymer supported acid catalyst. A range of compounds present in red wine and olive oil were deuteriated using these conditions. This procedure provides a facile route for the labelling of homovanillic alcohol, homovanillic acid, syringic acid, syringaldehyde and vanillin. This method is also applicable for the tritiation of these compounds. Copyright © 2001 John Wiley & Sons, Ltd.

  已经开发了一种用于去氘化大量含有酚和甲氧基取代基的芳香化合物的程序，使用了Nafion这一聚合物支持的酸催化剂。在这些条件下，对红酒和橄榄油中存在的一系列化合物进行了去氘化。该程序为同香草醇、同香草酸、香荚兰酸、香荚兰醛和香草醛的标记提供了一个简便的途径。该方法也适用于这些化合物的标记氚化。版权所有 © 2001 John Wiley & Sons, Ltd.
• A Selective Preparation of Highly Deuterated Hydroxybenzoic Acids
  作者：Kozo Nakamura、Kazuki Morozumi、Daisuke Amano

  DOI：10.2174/157017811795685036

  日期：2011.6.1

  A practical method to prepare selected deuterated hydroxybenzoic acids was developed. A hydroxybenzoic acid was dissolved or suspended in deuterium oxide (D2O), then deuterium chloride (DCl) was added to adjust the pD to 0.32, and the mixture was refluxed under nitrogen for one to six hours. After removing D2O and DCl by lyophilization, 2,6-dihydroxybenzoic-3,5-d2 acid, 3,5-dihydroxybenzoic-2,4,6-d3 acid, 3,5-dimethoxy-4-hydroxybezoic-2,6-d2 acid, and 3,4,5-trihydroxybenzoic-2,6-d2 acid were obtained quantitatively. Aromatic carbons with double substituent effects of hydroxy or methoxy groups were selectively deuterated. It was shown that the deuterium exchange reactions, which were electrophilic substitution reactions of deuterium cations to the aromatic carbons on the hydroxybenzoic acids, were regulated by the substituent effects. Deuteriums on all aromatic carbons were stable under a physiological condition and were detected in plasma by mass spectrometry analysis after oral administration to rats.

  开发了一种制备选定的氘代羟基苯甲酸的实用方法。将羟基苯甲酸溶解或悬浮在氧化氘(D 2 O)中，然后加入氯化氘(DCl)以调节pD至0.32，并将混合物在氮气下回流1至6小时。冻干除去D2O和DCl后，得到2,6-二羟基苯甲酸-3,5-d2酸、3,5-二羟基苯甲酸-2,4,6-d3酸、3,5-二甲氧基-4-羟基苯甲酸-2,6-定量获得d2酸和3,4,5-三羟基苯甲酸-2,6-d2酸。具有羟基或甲氧基双取代基作用的芳碳被选择性氘化。结果表明，氘交换反应是氘阳离子与羟基苯甲酸上芳香碳的亲电取代反应，受取代基效应的调节。所有芳香碳上的氘在生理条件下都很稳定，并且在给大鼠口服后通过质谱分析在血浆中检测到。