(Z)-2-hydroxy-6-(pentadec-10-en-1-yl)-benzoic acid | 110202-77-2

• 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: (Z)-2-hydroxy-6-(pentadec-10-en-1-yl)-benzoic acid
• 英文别名: (Z)-2-hydroxy-6-(pentadec-10-en-1-yl)benzoic acid；2-hydroxy-6-pentadec-10'(Z)-enylbenzoic acid；(15:1)-Δ¹⁰-anacardic acid；6-((Z)-pentadec-10-en-1-yl)salicylic acid；2-hydroxy-6-[(Z)-pentadec-10-enyl]benzoic acid
• CAS: 110202-77-2
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: UEOBFNCQTNUCCY-WAYWQWQTSA-N

物化性质

• 沸点：
  474.5±33.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (Z)-2-hydroxy-6-(pentadec-10-en-1-yl)-benzoic acid 以 乙醚 为溶剂， 生成 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid methyl ester
  参考文献：
  名称：

  New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights

  摘要：

  Bioassay-guided extraction of the stem bark of Knema laurina showed the acetylcholinesterase (AChE) inhibitory activity of DCM and hexane fractions. Further repeated column chromatography of hexane and DCM fractions resulted in the isolation and purification of five alkenyl phenol and salicylic acid derivatives. New compounds, (+)-2-hydroxy-6-(10'-hydroxypentadec-8'(E)-enyl)benzoic acid (1) and 3-pentadec-10'(Z)-enylphenol (2), along with known 3-heptadec-10'(Z)-enylphenol (3), 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid (4), and 2-hydroxy-6-(10'(Z)-heptadecenyl)benzoic acid (5) were isolated from the stem bark of this plant. Compounds (1-5) were tested for their acetylcholinesterase inhibitory activity. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and chemical derivatizations. Compound 5 showed strong acetylcholinesterase inhibitory activity with IC50 of 0.573 +/- 0.0260 mu M. Docking studies of compound 5 indicated that the phenolic compound with an elongated side chain could possibly penetrate deep into the active site of the enzyme and arrange itself through p-p interaction, H-bonding, and hydrophobic contacts with some critical residues along the complex geometry of the active gorge. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.065
• 作为产物：
  描述：

  ethyl 6-(chloromethyl)-2-methoxybenzoate 在 sodium hydroxide 、 sodium amalgam 、 lithium diisopropyl amide 、 乙硫醇钠 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-2-hydroxy-6-(pentadec-10-en-1-yl)-benzoic acid
  参考文献：
  名称：

  Prostaglandin Synthetase Inhibitors from the African Medicinal PlantOzoroa mucronata

  摘要：

  从O. mucronata中分离出了两种前列腺素合酶抑制剂——酚酸。通过光谱法确定了这些抑制剂的结构。报道了通过定向金属化合成这两种物质的高效方法。

  DOI：

  10.1246/cl.1987.1101

文献信息

• Syntheses of anacardic acids and ginkgoic acid
  作者：Yoshiro Yamagiwa、Kinji Ohashi、Yoshitaka Sakamota、Shinji Hirakawa、Tadao Kamikawa、Isao Kubo

  DOI：10.1016/s0040-4020(01)81629-x

  日期：——

  Syntheses of two anacardic acids [6-pentadecyl- and 6-(10-pentadecenyl) salicylic acid], inhibitors of prostaglandin synthetase and of the growth of certain insects, and ginkgoic acid via directive metallation is reported.

  据报导，合成了两种漆树酸[6-十五烷基和6-（10-十五碳烯基）水杨酸]，前列腺素合成酶的抑制剂和某些昆虫的生长，以及通过定向金属化作用生成的银杏酸。
• Zehnter, Reinhard; Gerlach, Hans, Liebigs Annalen, 1995, # 12, p. 2209 - 2220
  作者：Zehnter, Reinhard、Gerlach, Hans

  DOI：——

  日期：——
• YAMAGIWA, YOSHIRO;OHASHI, KINJI;SAKAMOTO, YOSHITAKA;HIRAKAWA, SHINJI;KAMI+, TETRAHEDRON, 43,(1987) N 15, 3387-3394
  作者：YAMAGIWA, YOSHIRO、OHASHI, KINJI、SAKAMOTO, YOSHITAKA、HIRAKAWA, SHINJI、KAMI+

  DOI：——

  日期：——
• Prostaglandin Synthetase Inhibitors from the African Medicinal Plant<i>Ozoroa mucronata</i>
  作者：Isao Kubo、Mujo Kim、Keizo Naya、Sakae Komatsu、Yoshiro Yamagiwa、Kinji Ohashi、Yoshitaka Sakamoto、Shinji Hirakawa、Tadao Kamikawa

  DOI：10.1246/cl.1987.1101

  日期：1987.6.5

  Two prostaglandin synthetase inhibitory anacardic acids were isolated from O. mucronata. The structures of these inhibitors were established by spectroscopic means. Efficient syntheses of these two via directive metallation were reported.

  从O. mucronata中分离出了两种前列腺素合酶抑制剂——酚酸。通过光谱法确定了这些抑制剂的结构。报道了通过定向金属化合成这两种物质的高效方法。
• New class of acetylcholinesterase inhibitors from the stem bark of Knema laurina and their structural insights
  作者：Muhammad Nadeem Akhtar、Kok Wai Lam、Faridah Abas、Maulidiani、Syahida Ahmad、Syed Adnan Ali Shah、Atta-ur-Rahman、M. Iqbal Choudhary、Nordin Hj Lajis

  DOI：10.1016/j.bmcl.2011.04.065

  日期：2011.7

  Bioassay-guided extraction of the stem bark of Knema laurina showed the acetylcholinesterase (AChE) inhibitory activity of DCM and hexane fractions. Further repeated column chromatography of hexane and DCM fractions resulted in the isolation and purification of five alkenyl phenol and salicylic acid derivatives. New compounds, (+)-2-hydroxy-6-(10'-hydroxypentadec-8'(E)-enyl)benzoic acid (1) and 3-pentadec-10'(Z)-enylphenol (2), along with known 3-heptadec-10'(Z)-enylphenol (3), 2-hydroxy-6-(pentadec-10'(Z)-enyl)benzoic acid (4), and 2-hydroxy-6-(10'(Z)-heptadecenyl)benzoic acid (5) were isolated from the stem bark of this plant. Compounds (1-5) were tested for their acetylcholinesterase inhibitory activity. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and chemical derivatizations. Compound 5 showed strong acetylcholinesterase inhibitory activity with IC50 of 0.573 +/- 0.0260 mu M. Docking studies of compound 5 indicated that the phenolic compound with an elongated side chain could possibly penetrate deep into the active site of the enzyme and arrange itself through p-p interaction, H-bonding, and hydrophobic contacts with some critical residues along the complex geometry of the active gorge. (C) 2011 Elsevier Ltd. All rights reserved.