N-(3,4-dihydroxyphenethyl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(3,4-dihydroxyphenethyl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide
• 英文别名: 4-hydroxy-3-methoxymandelic acid dopamide；N-(3,4-dihydroxyphenethyl)-2-hydroxy-2-(4-hydroxy-3 methoxyphenyl)acetamide；N-[2-(3,4-dihydroxyphenyl)ethyl]-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: YQZWOPKRNIDWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-羟基扁桃酸 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 52.0h， 生成 N-(3,4-dihydroxyphenethyl)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetamide
  参考文献：
  名称：

  Synthesis of polyhydroxylated aromatic mandelic acid amides and their antioxidative potential

  摘要：

  Six hydroxymandelic acid amides of phenolic amines were synthesized by condensation of 3,4-dihydroxymandelic or 4-hydroxy-3-methoxymandelic acid N-succinimidyl esters and several phenolic benzylamino and phenethylamino hydrochlorides in moderate to good yield. The radical scavenging activities determined by 2,2-diphenyl-1-picrylhydrazyl assay and superoxide trapping assay were superior compared to standards L-ascorbic acid, a-tocopherol, and butylated hydroxytoluene (BHT). The antioxidative activities tested by accelerated autoxidation of bulk Lipids were 2-3.5 times more potent compared to standards alpha -tocopherol and BHT. 3,4-Dihydroxymandelic acid dopamide (4b) and 4-hydroxy-3-methoxymandelic acid dopamide (4a) showed the best overall performance as antioxidants. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01136-4

文献信息

• Hydroxymandelic acid amides of phenolic amines
  申请人：Haarmann & Reimer GmbH

  公开号：US06265611B1

  公开（公告）日：2001-07-24

  The present invention relates to hydroxymandelic acid amides of phenolic amines which can be used as antioxidants or as free-radical scavengers, particularly in the cosmetic or dermatological field, in foods and in cosmetic and dermatological compositions.

  本发明涉及酚胺的羟基曼德酸酰胺，可用作抗氧化剂或自由基清除剂，特别是在化妆品或皮肤科领域中，以及在食品和化妆品和皮肤科组合物中使用。
• Hydroxymandelsäureamide phenolischer Amine
  申请人：HAARMANN & REIMER GMBH

  公开号：EP1029849A1

  公开（公告）日：2000-08-23

  Hydroxymandelsäureamide phenolischer Amine können als Antioxidantien oder als Radikalfänger, insbesondere auf dem kosmetischen oder dermatologischen Gebiet, in Nahrungsmitteln sowie in kosmetischen und dermatologischen Zusammensetzungen verwendet werden.

  酚胺的羟扁桃酸酰胺可用作抗氧化剂或自由基清除剂，特别是在化妆品或皮肤病领域、食品以及化妆品和皮肤病组合物中。
• US6265611B1
  申请人：——

  公开号：US6265611B1

  公开（公告）日：2001-07-24
• Synthesis of polyhydroxylated aromatic mandelic acid amides and their antioxidative potential
  作者：Jakob P Ley、Heinz-Jürgen Bertram

  DOI：10.1016/s0040-4020(00)01136-4

  日期：2001.2

  Six hydroxymandelic acid amides of phenolic amines were synthesized by condensation of 3,4-dihydroxymandelic or 4-hydroxy-3-methoxymandelic acid N-succinimidyl esters and several phenolic benzylamino and phenethylamino hydrochlorides in moderate to good yield. The radical scavenging activities determined by 2,2-diphenyl-1-picrylhydrazyl assay and superoxide trapping assay were superior compared to standards L-ascorbic acid, a-tocopherol, and butylated hydroxytoluene (BHT). The antioxidative activities tested by accelerated autoxidation of bulk Lipids were 2-3.5 times more potent compared to standards alpha -tocopherol and BHT. 3,4-Dihydroxymandelic acid dopamide (4b) and 4-hydroxy-3-methoxymandelic acid dopamide (4a) showed the best overall performance as antioxidants. (C) 2001 Elsevier Science Ltd. All rights reserved.