sinapic acid N-hydroxysuccinimidyl ester | 582311-53-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: sinapic acid N-hydroxysuccinimidyl ester
• 英文别名: N-succinimidyl 3,5-dimethoxy-4-hydroxy-E-cinnamate；(2,5-dioxopyrrolidin-1-yl) (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• CAS: 582311-53-3
• 化学式: C₁₅H₁₅NO₇
• 分子量: 321.287
• InChiKey: BDDZVDBUESBHKP-ZZXKWVIFSA-N

物化性质

• 沸点：
  484.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-3,4-二羟基苯基丙氨酸甲酯盐酸 、 sinapic acid N-hydroxysuccinimidyl ester 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 methyl (S,E)-3-(3,4-dihydroxyphenyl)-2-(3-(4-hydroxy-3,5-dimethoxyphenyl)acrylamido)propionate
  参考文献：
  名称：

  Synthesis of Lipophilic Clovamide Derivatives and Their Antioxidative Potential against Lipid Peroxidation

  摘要：

  Some N-(hydroxycinnamoyl)-L-tyrosine and L-DOPA alkyl esters were synthesized and evaluated as a variation of the clovamide (N-caffeoyl-L-3,4-dihydroxyphenylalanine) structure, a known antioxidant found in red clover. The amides were prepared in good yields starting from methyl and dodecylesters Of L-tyrosine and L-DOPA by reacting with the N-hydroxysuccinimidyl esters of ferulic, sinapic, and acetyl-protected caffeic acid, respectively. In the DPPH. (2,2-diphenyl-1-picrylhydrazyl) and superoxide radical quencher assays they showed radical scavenging activity equal to or higher than those of the standard antioxidants ascorbic acid and tocopherol. The antioxidative potentials of the clovamide derivatives against bulk lipid oxidation, as determined by the accelerated autoxidation of oils, were equal to or higher than those of the standard antioxidants; some of the compounds were able to protect an emulsion of linoleic acid/beta-carotene against oxidation. N-Caffeoyl L-tyrosine methyl ester and the N-cinnamoyl L-DOPA alkyl esters especially were potent antioxidants in bulk lipids and moderate protectants in emulsions.

  DOI：

  10.1021/jf034286d
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 3,5-二甲氧基-4-羟基肉桂酸 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 sinapic acid N-hydroxysuccinimidyl ester
  参考文献：
  名称：

  植物提取物中羟基肉桂酰辅酶a硫酯的磷酸水解

  摘要：

  摘要 在大麦幼苗提取物中，对香豆酰-CoA 迅速水解为对香豆酰-脱磷酸-CoA、对-香豆酰-4'-磷酸泛酰巯基乙胺和对香豆酰-泛酰巯基乙胺。对香豆酰-4'-磷酸泛酰巯基乙胺在对香豆酰-胍丁胺形成过程中作为胍丁香豆酰转移酶的底物具有活性，但对香豆酰-泛酰巯基乙胺是无活性的。磷酸化水解可被无机焦磷酸盐、氟化钠和嘌呤核苷酸部分抑制。还描述了合成羟基肉桂酸的 N-羟基琥珀酰亚胺酯的简化方法，用于合成 CoA 硫酯。

  DOI：

  10.1016/0031-9422(84)83072-1

文献信息

• Phenolsäureamide hydroxysubstituierter Benzylamine
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0900781B1

  公开（公告）日：2002-03-20
• US6117365A
  申请人：——

  公开号：US6117365A

  公开（公告）日：2000-09-12
• Synthesis of Lipophilic Clovamide Derivatives and Their Antioxidative Potential against Lipid Peroxidation
  作者：Jakob P. Ley、Heinz-Jürgen Bertram

  DOI：10.1021/jf034286d

  日期：2003.7.1

  Some N-(hydroxycinnamoyl)-L-tyrosine and L-DOPA alkyl esters were synthesized and evaluated as a variation of the clovamide (N-caffeoyl-L-3,4-dihydroxyphenylalanine) structure, a known antioxidant found in red clover. The amides were prepared in good yields starting from methyl and dodecylesters Of L-tyrosine and L-DOPA by reacting with the N-hydroxysuccinimidyl esters of ferulic, sinapic, and acetyl-protected caffeic acid, respectively. In the DPPH. (2,2-diphenyl-1-picrylhydrazyl) and superoxide radical quencher assays they showed radical scavenging activity equal to or higher than those of the standard antioxidants ascorbic acid and tocopherol. The antioxidative potentials of the clovamide derivatives against bulk lipid oxidation, as determined by the accelerated autoxidation of oils, were equal to or higher than those of the standard antioxidants; some of the compounds were able to protect an emulsion of linoleic acid/beta-carotene against oxidation. N-Caffeoyl L-tyrosine methyl ester and the N-cinnamoyl L-DOPA alkyl esters especially were potent antioxidants in bulk lipids and moderate protectants in emulsions.
• The phosphohydrolysis of hydroxycinnamoyl-coenzyme a thioesters in plant extracts
  作者：Jonathan Negrel、Terence A. Smith

  DOI：10.1016/0031-9422(84)83072-1

  日期：1984.1

  Abstract In barley seedling extracts, p -coumaroyl-CoA is rapidly hydrolysed to p -coumaroyl-dephospho-CoA, p -coumaroyl-4′-phosphopantetheine and p -coumaroyl-pantetheine. p -Coumaroyl-4′-phosphopantetheine is active as a substrate of agmatine coumaroyl transferase in the formation of p -coumaroyl-agmatine, but p -coumaroyl-pantetheine is inactive. The phosphohydrolysis can be partly inhibited by inorganic

  摘要 在大麦幼苗提取物中，对香豆酰-CoA 迅速水解为对香豆酰-脱磷酸-CoA、对-香豆酰-4'-磷酸泛酰巯基乙胺和对香豆酰-泛酰巯基乙胺。对香豆酰-4'-磷酸泛酰巯基乙胺在对香豆酰-胍丁胺形成过程中作为胍丁香豆酰转移酶的底物具有活性，但对香豆酰-泛酰巯基乙胺是无活性的。磷酸化水解可被无机焦磷酸盐、氟化钠和嘌呤核苷酸部分抑制。还描述了合成羟基肉桂酸的 N-羟基琥珀酰亚胺酯的简化方法，用于合成 CoA 硫酯。