α-Valerensaeure-methylester | 203304-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: α-Valerensaeure-methylester
• 英文别名: valerenic acid methyl ester；2-Methyl-3-(3,7-dimethyl-2,4,5,6,7,7a-hexahydro-indenyl-(4))-acrylsaeure-methylester
• CAS: 203304-41-0
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: OQZLCTPJWLOFKS-RQIXTAMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-Valerensaeure-methylester 在 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 生成 Valerenol
  参考文献：
  名称：

  Bohlmann, Ferdinand; Lonitz, Michael, Chemische Berichte, 1980, vol. 113, # 7, p. 2410 - 2423

  摘要：

  DOI：
• 作为产物：
  描述：

  [(4R,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]methanol 在 吡啶 、 chromium(VI) oxide 、 苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 α-Valerensaeure-methylester
  参考文献：
  名称：

  Bohlmann, Ferdinand; Lonitz, Michael, Chemische Berichte, 1980, vol. 113, # 7, p. 2410 - 2423

  摘要：

  DOI：

文献信息

• Highly Potent Modulation of GABAA Receptors by Valerenic Acid Derivatives
  作者：Sascha Kopp、Roland Baur、Erwin Sigel、Hanns Möhler、Karl-Heinz Altmann

  DOI：10.1002/cmdc.201000062

  日期：2010.5.3

  Traditional medicine to potent drug leads: Valerenic acid (1) is a major constituent of common valerian and potentiates the effect of γ‐aminobutyric acid on GABAA receptors. Through systematic modification of the carboxyl group of 1 we have discovered a noncarboxylate‐containing analogue, tetrazole 10, which exceeds the modulatory activity of 1 at GABAA receptors by one order of magnitude.

  传统药物对潜在药物的潜在影响：缬草酸（1）是缬草的主要成分，可增强γ-氨基丁酸对GABA A受体的作用。通过对1的羧基进行系统修饰，我们发现了一个不含羧酸盐的类似物四唑10，其对GABA A受体的调节活性超出1的一个数量级。
• Esters of valerenic acid as potential prodrugs
  作者：Juliane Hintersteiner、Maximilian Haider、Denise Luger、Christoph Schwarzer、Gottfried Reznicek、Walter Jäger、Sophia Khom、Marko D. Mihovilovic、Steffen Hering

  DOI：10.1016/j.ejphar.2014.03.019

  日期：2014.7

  Valerenic acid (VA) is a beta(2/3) subunit-specific modulator of gamma-aminobutyric acid (GABA) type A (GABA(A)) receptors inducing anxiolysis. Here we analyze if VA-esters can serve as prodrugs and if different ester structures have different in vitro/in vivo effects. Modulation of GABA(A) receptors expressed in Xenopus oocytes was studied with 2-microelectrode-voltage-clamp. Anxiolytic effects of the VA-esters were studied on male C57BL/6N mice by means of the elevated plus maze-test; anticonvulsant properties were deduced from changes in seizure threshold upon pentylenetetrazole infusion. VA was detected in plasma confirming hydrolysis of the esters and release of VA in vivo. Esterification significantly reduced the positive allosteric modulation of GABA(A) (alpha(1)beta(3)gamma(2S)) receptors in vitro, in vivo, the studied VA-ester derivatives induced similar or even stronger anxiolytic and anticonvulsant action than VA. While methylation and propylation of VA resulted in faster onset of anxiolysis, the action of VA-ethylester was longer lasting, but occurred with a significant delay. The later finding is in line with the longer lasting anticonvulsant effects of this compound. The estimated VA plasma concentrations provided first insight into the release kinetics from different VA-esters. This might be an important step for its future clinical application as a potential non-sedative anxiolytic and anticonvulsant (C) 2014 The Authors. Published by Elsevier B.V. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/3.0/).
• TERPENES. XIV. THE STRUCTURE OF VALERENIC ACID¹
  作者：G. Büchi、T. L. Popper、D. Stauffacher

  DOI：10.1021/ja01496a069

  日期：1960.6