coniferyl (E)-8-methyl-6-nonenoate | 946572-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: coniferyl (E)-8-methyl-6-nonenoate
• 英文别名: capsiconiate；[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] (E)-8-methylnon-6-enoate
• CAS: 946572-73-2
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: ZEWSMOFWZCBFSU-OAMUUVBCSA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)
• 溶解度：
  乙醇中≤20mg/ml；DMSO 中≤20mg/ml；二甲基甲酰胺中≤20mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 储存条件：
  -20°C，密封保存，置于干燥处。

制备方法与用途

capsiconiate（对异戊烯基(顺)-8-甲基-6-壬烯酸酯）是一种TRPV1激动剂（EC50=3.2 μM）。它可以用于研究由TRPV1介导的疾病，如疼痛、炎症和癫痫。

反应信息

• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 、 （6E）-8-甲基--6-壬烯酸甲基酯-d3 在 Novozym 435 4 A molecular sieve 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以13.1%的产率得到coniferyl (E)-8-methyl-6-nonenoate
  参考文献：
  名称：

  Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1

  摘要：

  Coniferyl esters-capsiconiate and dihydrocapsiconiate-were isolated from the fruits of the pepper, Capsicum baccatum L. var. praetermissum. Their structures were determined by spectroscopic methods to be coniferyl (E)-8-methyl-6-nonenoate (capsiconiate) and coniferyl 8-methylnonanoate (dihydrocapsiconiate). This finding was further confirmed by the lipase-catalyzed condensation of coniferyl alcohol with its corresponding fatty acid derivative. The agonist activity of the esters for transient receptor potential vanilloid I (TRPV1) was evaluated by conducting an analysis of the intracellular calcium concentrations in TRPV1-expressing HEK293 cells. The EC50 values of capsiconiate and dihydrocapsiconiate were 3.2 and 4.2 mu M, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.11.017

文献信息

• Isolation of coniferyl esters from Capsicum baccatum L., and their enzymatic preparation and agonist activity for TRPV1
  作者：Kenji Kobata、Hitomi Tate、Yusaku Iwasaki、Yoshiyuki Tanaka、Keigo Ohtsu、Susumu Yazawa、Tatsuo Watanabe

  DOI：10.1016/j.phytochem.2007.11.017

  日期：2008.3

  Coniferyl esters-capsiconiate and dihydrocapsiconiate-were isolated from the fruits of the pepper, Capsicum baccatum L. var. praetermissum. Their structures were determined by spectroscopic methods to be coniferyl (E)-8-methyl-6-nonenoate (capsiconiate) and coniferyl 8-methylnonanoate (dihydrocapsiconiate). This finding was further confirmed by the lipase-catalyzed condensation of coniferyl alcohol with its corresponding fatty acid derivative. The agonist activity of the esters for transient receptor potential vanilloid I (TRPV1) was evaluated by conducting an analysis of the intracellular calcium concentrations in TRPV1-expressing HEK293 cells. The EC50 values of capsiconiate and dihydrocapsiconiate were 3.2 and 4.2 mu M, respectively. (c) 2007 Elsevier Ltd. All rights reserved.