(–)-trans-N-p-coumaroyl octopamine | 66648-45-1

• 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-p-coumaroyl octopamine
• 英文别名: N-trans-p-coumaroyl octopamine；N-trans-p-coumaroyloctopamine；trans-N-p-coumaroyloctopamine；N-trans-coumaroyloctopamine；N-p-coumaroyloctopamine；p-coumaroyloctopamine；(E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide
• CAS: 66648-45-1
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: VATOSFCFMOPAHX-XCVCLJGOSA-N

物化性质

• 沸点：
  638.9±55.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  214-215°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

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

生物活性化合物 N-trans-p-coumaroyloctopamine 是从茄子（学名：Solanum melongena L.）中分离得到的一种苯丙醇胺。

反应信息

• 作为反应物：
  描述：

  (–)-trans-N-p-coumaroyl octopamine 、 乙酸酐 在 吡啶 作用下， 生成 triacetyl N-trans-p-coumaroyl octopamine
  参考文献：
  名称：

  Yoshihara, Teruhiko; Yamaguchi, Katsuyoshi; Takamatsu, Seiji, Agricultural and Biological Chemistry, 1981, vol. 45, # 11, p. 2593 - 2598

  摘要：

  DOI：
• 作为产物：
  描述：

  对羟基苯甲醛 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-p-coumaroyl 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

• 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。
• [EN] METHODS FOR REVERSING HEPATIC STEATOSIS<br/>[FR] PROCÉDÉS D'INVERSION DE LA STÉATOSE HÉPATIQUE
  申请人：[en]BRIGHTSEED, INC.

  公开号：WO2022081567A1

  公开（公告）日：2022-04-21

  Disclosed herein are methods for reversing hepatic steatosis by providing a consumable composition. Some embodiments provided include, for example, administering a compound of Formula (I) or compound of Formula (II). Some embodiments provide the composition is formulated as a dietary supplement, food ingredient or additive, a medical food, nutraceutical or pharmaceutical composition.
• 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.
• 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：——