Malonic acid mono-(1-methyl-heptyl) ester | 877080-16-5

• 英文名称: Malonic acid mono-(1-methyl-heptyl) ester
• 英文别名: 3-Octan-2-yloxy-3-oxopropanoic acid
• CAS: 877080-16-5
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: LOKNWBSGOAOTAK-UHFFFAOYSA-N

物化性质

• 沸点：
  190-193 °C(Press: 2 Torr)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  15.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Malonic acid mono-(1-methyl-heptyl) ester 、 3,4-二羟基苯甲醛 在 哌啶 、 吡啶 作用下， 以 甲苯 为溶剂， 生成 Octan-2-yl-3-(3,4-dihydroxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines

  摘要：

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.046
• 作为产物：
  描述：

  malonic acid bis-(1-methyl-heptyl ester) 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以81.2%的产率得到Malonic acid mono-(1-methyl-heptyl) ester
  参考文献：
  名称：

  Xia, Chun-Nian; Hu, Wei-Xiao, Journal of Chemical Research, 2005, # 5, p. 332 - 334

  摘要：

  DOI：

文献信息

• Evaluation of the antimicrobial and antioxidant properties of synthetic phenolipids
  作者：Horiya Nassiba Ham、Matthieu M. Mention、Blandine Godon、Fanny Brunissen、Manon Thomas、Florent Allais、Michel Lopez、Nabila Imatoukene

  DOI：10.1016/j.procbio.2024.03.015

  日期：2024.6

  of phenolic compounds by lipophilization allowing the synthesis of new compounds with improved biological properties. This study aims to investigate the antimicrobial effects of eight synthesized phenolipids, derived from bioactive coumaric and ferulic acid esters, against , , and . Antioxidant activity, as well as antimicrobial capacity were evaluated through DPPH assays and classical disc agar diffusion

  通过亲脂化对酚类化合物进行官能化，从而可以合成具有改善的生物特性的新化合物。本研究旨在研究源自生物活性香豆酸酯和阿魏酸酯的八种合成酚脂对 、 、 和 的抗菌作用。分别通过 DPPH 测定和经典圆盘琼脂扩散评估抗氧化活性以及抗菌能力，同时使用流式细胞术测定评估细胞活力。抗氧化活性结果表明阿魏酸酯比香豆酸酯表现出更高的抗自由基活性。琼脂扩散测定结果表明，1-甲基丙基香豆酸酯和 1-甲基丙基阿魏酸酯 (1-MPF) 对所有测试的微生物均具有有效的抗菌活性，最低抑制浓度 (MIC) 值在 0.9 至 3.5 mM 之间。此外，流式细胞术显示 1-MPF 和香豆酸癸酯表现出显着的杀菌活性 (p < 0.05)，几乎有 63% 的细胞死亡。与常用的琼脂方法相比，流式细胞术被证明是一种快速、直接的分析工具，可以评估抗菌活性，同时提供抑制类型的信息。这些结果表明酚脂作为有效的亲脂性生物活性分子可用于保护食
• Hu, Wei-Xiao; Xia, Chun-Nian; Wang, Guo-Hong, Journal of Chemical Research, 2006, # 9, p. 586 - 588
  作者：Hu, Wei-Xiao、Xia, Chun-Nian、Wang, Guo-Hong、Zhou, Wei

  DOI：——

  日期：——
• Synthesis and antitumor activity of feruloyl and caffeoyl derivatives
  作者：Hui-zhen Chen、You-bao Chen、Ya-ping Lv、Fang Zeng、Juan Zhang、Yong-lie Zhou、Han-bing Li、Li-fei Chen、Bin-jie Zhou、Jian-rong Gao、Chun-nian Xia

  DOI：10.1016/j.bmcl.2014.08.024

  日期：2014.9

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.