(–)-trans-N-feruloyl octopamine | 66648-44-0

• 物质功能分类: 天然产物 - 生物碱
• 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: (–)-trans-N-feruloyl octopamine
• 英文别名: (R)-N-trans-feruloyloctopamine；trans-(N-feruloyl)octopamine；N-trans-feruloyl octopamine；N-trans-feruloyloctopamine；trans-N-feruloyloctopamine；N-trans-Feruloyloctopamin；(E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• CAS: 66648-44-0
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: VJSCHQMOTSXAKB-YCRREMRBSA-N

物化性质

• 沸点：
  652.5±55.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  164-165°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 储存条件：
  储存条件：2-8℃，干燥，密封保存。

制备方法与用途

用途

N-阿魏酰章鱼胺作为一种阿魏酸酰胺类化合物，在医药和化工领域有着广泛的应用。

制备

该化合物以廉价易得的香兰素为原料，通过克脑文盖尔(Knoevenagel)缩合反应得到阿魏酸。随后，使用N,N′-二环己基碳酰亚胺(DCC)作为脱水剂和4-二甲氨基吡啶(DMAP)作为催化剂，与奥克巴胺反应合成N-阿魏酰章鱼胺。其合成过程如下图所示：

生物活性

从大蒜皮中分离出的N-Feruloyloctopamine是一种抗氧化剂成分，能够显著降低Akt和p38 MAPK的磷酸化水平。

靶点

Akt
p38 MAPK

反应信息

• 作为反应物：
  描述：

  N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 (–)-trans-N-feruloyl octopamine 反应 0.25h， 生成
  参考文献：
  名称：

  茄属植物细胞培养物中羟基肉桂酰胺和α-羟基乙酰香草酮的形成

  摘要：

  摘要 在经过诱导剂处理的光混合营养型 Solanum khasianum 细胞培养物中，细胞培养基中积累了九种酚类化合物。它们被分离出来并在结构上被鉴定为 N-p-香豆酰氯多巴胺、N-阿魏酰氯多巴胺、N-p-香豆酰酪胺和 N-阿魏酰苯胺以及 α-羟基乙酰香草酮的顺式和反式异构体。羟基肉桂酰基部分的顺式异构体仅在培养物光照期间形成。根据化合物的不同，羟基肉桂酰胺在激发后 6 到 24 小时之间显示出最大值。化合物的减少很可能是过氧化物酶介导的反应。

  DOI：

  10.1016/0031-9422(96)00173-2
• 作为产物：
  描述：

  香草醛 在 哌啶 、 吡啶 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (–)-trans-N-feruloyl octopamine
  参考文献：
  名称：

  Synthesis and structure–activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation

  摘要：

  Phenylpropanoid amides of octopamine (OA) 1a-1e and dopamine (DA) 2a-2e were synthesised and the structure-activity relationships (SARs) for antioxidant and tyrosinase inhibition activities were analysed. Among synthesised compounds, 2c, which contains two catechol moieties, exhibited the most DPPH radical-scavenging activity (EC50 = 16.2 +/- 2.41 mu M), and id exhibited significant tyrosinase inhibitory activity (IC50 = 5.3 +/- 1.8 mu M). Interestingly, with the same acid moiety, OA derivatives showed more inhibitory effect on tyrosinase than did compounds derived from DA, whereas DA derivatives were found to have higher antioxidant activity than compounds derived from OA. The relationship between their structures and their potencies, demonstrated in the current study, will be useful for the design of optimal agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.02.152

文献信息

• Yoshihara, Teruhiko; Yamaguchi, Katsuyoshi; Takamatsu, Seiji, Agricultural and Biological Chemistry, 1981, vol. 45, # 11, p. 2593 - 2598
  作者：Yoshihara, Teruhiko、Yamaguchi, Katsuyoshi、Takamatsu, Seiji、Sakamura, Sadao

  DOI：——

  日期：——
• Synthesis and structure–activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation
  作者：Zhengrong Wu、Lifang Zheng、Yang Li、Feng Su、Xiaoxuan Yue、Wei Tang、Xiaoyan Ma、Junyu Nie、Hongyu Li

  DOI：10.1016/j.foodchem.2012.02.152

  日期：2012.9

  Phenylpropanoid amides of octopamine (OA) 1a-1e and dopamine (DA) 2a-2e were synthesised and the structure-activity relationships (SARs) for antioxidant and tyrosinase inhibition activities were analysed. Among synthesised compounds, 2c, which contains two catechol moieties, exhibited the most DPPH radical-scavenging activity (EC50 = 16.2 +/- 2.41 mu M), and id exhibited significant tyrosinase inhibitory activity (IC50 = 5.3 +/- 1.8 mu M). Interestingly, with the same acid moiety, OA derivatives showed more inhibitory effect on tyrosinase than did compounds derived from DA, whereas DA derivatives were found to have higher antioxidant activity than compounds derived from OA. The relationship between their structures and their potencies, demonstrated in the current study, will be useful for the design of optimal agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Formation of hydroxycinnamoylamides and α-hydroxyacetovanillone in cell cultures of Solanum khasianum
  作者：Ute Mühlenbeck、Albertus Kortenbusch、Wolfgang Barz

  DOI：10.1016/0031-9422(96)00173-2

  日期：1996.8

  Abstract In elicitor-treated photomixotrophic Solanum khasianum cell cultures, nine phenolic compounds accumulated in the cell culture medium. They were isolated and structurally identified as the cis - and trans -isomers of N - p -coumaroyloctopamine, N -feruloyloctopamine, N - p -coumaroyltyramine and N -feruloyltyramine as well as α-hydroxyacetovanillone. The cis -isomers of the hydroxycinnamoyl moieties

  摘要 在经过诱导剂处理的光混合营养型 Solanum khasianum 细胞培养物中，细胞培养基中积累了九种酚类化合物。它们被分离出来并在结构上被鉴定为 N-p-香豆酰氯多巴胺、N-阿魏酰氯多巴胺、N-p-香豆酰酪胺和 N-阿魏酰苯胺以及 α-羟基乙酰香草酮的顺式和反式异构体。羟基肉桂酰基部分的顺式异构体仅在培养物光照期间形成。根据化合物的不同，羟基肉桂酰胺在激发后 6 到 24 小时之间显示出最大值。化合物的减少很可能是过氧化物酶介导的反应。