(R)-1-phenylethyl (S)-2-methylbutanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-phenylethyl (S)-2-methylbutanoate
• 英文别名: [(1R)-1-phenylethyl] (2S)-2-methylbutanoate
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: KOQHMJIFZXCPNR-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-O-β-D-[6-(S)-2-methylbutanoyl]glucopyranosylcinnamic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 18.0h， 生成 (R)-1-phenylethyl (S)-2-methylbutanoate
  参考文献：
  名称：

  Phenolics from Durian Exert Pronounced NO Inhibitory and Antioxidant Activities

  摘要：

  Durian, known as the king of fruits, is native to Southeast Asia and popular in many countries. Bioactivity-guided fractionation of the peel of durian was applied to determine its bioactive constituents. Four novel phenolics, along with 16 known, were purified and identified: Four novel phenolics were elucidated to be durianol A (1), durianol B (2), durianol C (3), and 5'-methoxy-7'-epi-jatrorin A (4), respectively. The antioxidant and NO inhibitory activities were evaluated for the isolated phenolics. Some phenolics showed significant antioxidant activity in the DPPH and superoxide anion radical scavenging capacity assay. Most of the phenolics revealed pronounced inhibitory effects on NO production in murine RAW 264.7 cells included by LPS, which showed more potent NO inhibitory activity compared to indomethacin. The results strongly demonstrated that the phenolics may be partially responsible for durian's NO inhibitory activity.

  DOI：

  10.1021/acs.jafc.6b01580

文献信息

• Resin Glycoside Constituents of <i>Ipomoea pes-caprae</i> (Beach Morning Glory)
  作者：Hongwen Tao、Xiaojiang Hao、Jinggen Liu、Jian Ding、Yuchun Fang、Qianqun Gu、Weiming Zhu

  DOI：10.1021/np800386z

  日期：2008.12.26

  Eight new resin glycosides, pescapreins X-XVII (1-8), were isolated from a lipophilic fraction of an ethanol extract of the entire plant of beach morning glory, Ipomoea pes-caprae. Their structures were elucidated by spectroscopic data analysis and by chemical transformation. These compounds were evaluated biologically in terms of cancer cell line cytotoxicity, antibacterial and antifungal activity

  从整个海滩牵牛花植物番薯科植物番薯角豆科植物的乙醇提取物中，从脂溶性部分中分离出八种新的树脂糖苷，倍半素X-XVII（1-8）。通过光谱数据分析和化学转化来阐明它们的结构。从癌细胞系的细胞毒性，抗菌和抗真菌活性以及对阿片类药物受体的影响方面对这些化合物进行了生物学评估。
• Anti-inflammatory components of Chrysanthemum indicum flowers
  作者：Bui Thi Thuy Luyen、Bui Huu Tai、Nguyen Phuong Thao、Ji Yun Cha、Hoon Yeon Lee、Young Mi Lee、Young Ho Kim

  DOI：10.1016/j.bmcl.2014.11.054

  日期：2015.1

  One new octulosonic acid derivative, chrysannol A (1), along with 17 known compounds (2-18), were isolated from Chrysanthemum indicum flowers. Their structures were determined from 1D NMR, 2D NMR, HR-ESI-MS spectral data, and comparisons with previous reports. The effects of these compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor alpha (TNF-alpha) production by RAW 264.7 cells were investigated. Compound 8 showed the highest inhibition of NO production of 46.09% at a concentration of 10.0 mu M. Compounds 7, 10, 11, and 16 inhibited TNF-alpha secretion at all concentration tested (0.4, 2.0, and 10.0 mu M), with inhibition values ranging from 22.27% to 33.13%. In addition, compound 8 and 9 decrease COX-2 and iNOS protein on Western blot analysis in dose dependent manner. (C) 2014 Elsevier Ltd. All rights reserved.
• Phenolics from Durian Exert Pronounced NO Inhibitory and Antioxidant Activities
  作者：Jianying Feng、Yihai Wang、Xiaomin Yi、Weimin Yang、Xiangjiu He

  DOI：10.1021/acs.jafc.6b01580

  日期：2016.6.1

  Durian, known as the king of fruits, is native to Southeast Asia and popular in many countries. Bioactivity-guided fractionation of the peel of durian was applied to determine its bioactive constituents. Four novel phenolics, along with 16 known, were purified and identified: Four novel phenolics were elucidated to be durianol A (1), durianol B (2), durianol C (3), and 5'-methoxy-7'-epi-jatrorin A (4), respectively. The antioxidant and NO inhibitory activities were evaluated for the isolated phenolics. Some phenolics showed significant antioxidant activity in the DPPH and superoxide anion radical scavenging capacity assay. Most of the phenolics revealed pronounced inhibitory effects on NO production in murine RAW 264.7 cells included by LPS, which showed more potent NO inhibitory activity compared to indomethacin. The results strongly demonstrated that the phenolics may be partially responsible for durian's NO inhibitory activity.