8-methlnonanoic acid (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-yl ester | 946572-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 8-methlnonanoic acid (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-yl ester
• 英文别名: coniferyl 8-methylnonanoate；dihydrocapsiconiate；8-Methylnonanoic acid (E)-3-(3-methoxy-4-hydroxyphenyl)-2-propenyl ester；[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl] 8-methylnonanoate
• CAS: 946572-74-3
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: MPGLKHMQOVOUKA-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-methylnonanoic acid 、 反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 Novozym 435 4 A molecular sieve 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以22.5%的产率得到8-methlnonanoic acid (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-yl ester
  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.