3,4-dihydroxymandelic acid N-succinimidyl ester | 335591-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,4-dihydroxymandelic acid N-succinimidyl ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-(3,4-dihydroxyphenyl)-2-hydroxyacetate
• CAS: 335591-55-4
• 化学式: C₁₂H₁₁NO₇
• 分子量: 281.222
• InChiKey: ZVKDYPUOHWMJFC-UHFFFAOYSA-N

物化性质

• 沸点：
  537.8±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  香兰素胺盐酸盐 、 3,4-dihydroxymandelic acid N-succinimidyl ester 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以296 mg的产率得到2-(3,4-dihydroxyphenyl)-2-hydroxy-N-(4-hydroxy-3-methoxybenzyl)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
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 DL-3,4-二羟基扁桃酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 3,4-dihydroxymandelic acid N-succinimidyl ester
  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

• 3,4-Dihydroxymandelic acid alkylamides and use thereof
  申请人：——

  公开号：US20030171617A1

  公开（公告）日：2003-09-11

  The invention relates to N-alkyl-2-(3,4-dihydroxyphenyl)-2-hydroxyacetamides and to cosmetic and/or pharmaceutical preparations and foods comprising these compounds.

  本发明涉及N-烷基-2-(3,4-二羟基苯基)-2-羟基乙酰胺以及含有这些化合物的化妆品和/或药物制剂和食品。
• 3,4-DIHYDROXYMANDELSÄUREALKYLAMIDE UND IHRE VERWENDUNG
  申请人：HAARMANN & REIMER GMBH

  公开号：EP1296937A1

  公开（公告）日：2003-04-02
• [DE] 3,4-DIHYDROXYMANDELSÄUREALKYLAMIDE UND IHRE VERWENDUNG<br/>[EN] 3,4-DIHYDROXYMANDELIC ACID ALKYLAMIDES AND USE THEREOF<br/>[FR] 3,4-ALKYLAMIDES D'ACIDE DIHYDROXYMANDELIQUE ET LEURS UTILISATION
  申请人：HAARMANN & REIMER GMBH

  公开号：WO2001098258A1

  公开（公告）日：2001-12-27

  Neue 3,4-Dihydroxymandelsäurealkylamide sowie kosmetische und pharmazeutische Zubereitungen oder Nahrungsmittel, die diese Verbindungen enthalten, können in physiologischen Systemen die natürlichen Abwehrmechanismen gegen freie Radikale und reaktive Sauerstoffverbindungen unterstützen oder in Kosmetika, Pharmazeutika oder Nahrungs- oder Genussmitteln deren oxidationsempfindlichen Bestandteile vor Autoxidation schützen.
• 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.