methyl rosmarinate | 203798-86-1

• 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: methyl rosmarinate
• 英文别名: (S)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl (E)-3-(3,4-dihydroxyphenyl)acrylate；methyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate
• CAS: 203798-86-1
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: XHALVRQBZGZHFE-PFWMLDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl rosmarinate 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Synthese der enantiomeren (+)- und (−)-Rosmarinsäuremethylester

  摘要：

  DOI：

  10.1007/pl00010154
• 作为产物：
  描述：

  (S)-3-(3,4-Bis-benzyloxy-phenyl)-2-hydroxy-propionic acid methyl ester 在 4-二甲氨基吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 methyl rosmarinate
  参考文献：
  名称：

  Synthese der enantiomeren (+)- und (−)-Rosmarinsäuremethylester

  摘要：

  DOI：

  10.1007/pl00010154

文献信息

• Relationship between Hydrophobicity and Antioxidant Ability of “Phenolipids” in Emulsion: A Parabolic Effect of the Chain Length of Rosmarinate Esters
  作者：Mickaël Laguerre、Luis J. López Giraldo、Jérôme Lecomte、Maria-Cruz Figueroa-Espinoza、Bruno Baréa、Jochen Weiss、Eric A. Decker、Pierre Villeneuve

  DOI：10.1021/jf904119v

  日期：2010.3.10

  The polar paradox predicts that hydrophobic antioxidants are more active in emulsions than their hydrophilic homologues, thus assuming a linear dependency between hydrophobicity and antioxidant capacity. In contrast, we formulate in this paper an alternative hypothesis assuming a possible nonlinear dependency. To verify this so-called "nonlinear hypothesis", the antioxidant capacity of a homologous series of rosmarinic acid and its alkyl esters (methyl, butyl, octyl, dodecyl, hexadecyl, octadecyl, and eicosyl) was evaluated using a newly developed conjugated autoxidizable triene (CAT) assay. It appeared that the antioxidant capacity increases as the alkyl chain is lengthened, with a maximum for the octyl chain, after which further chain extension leads to a collapse in antioxidant capacity, This nonlinear effect was discussed in relation to the "cutoff effect" generally observed in studies using cultured cells. This new hypothesis may provide a better understanding of the antioxidant behavior of phenolics in emulsion which is a key to develop new antioxidant strategies to protect lipid substrates from oxidation. Moreover, the lipophilization with medium chain appeared as a promising way to enhance the antioxidant capacity of phenolics since octyl rosmarinate was three times more effective than rosmarinic acid which is already one of the most powerful known phenolic antioxidant. Finally, this work paves the way for systematic investigation of the chain length effect to design new "phenolipids" in a rational fashion.
• Synthese der enantiomeren (+)- und (−)-Rosmarinsäuremethylester
  作者：Eberhard Reimann、Thomas Pflug

  DOI：10.1007/pl00010154

  日期：1998.2