异木香酸 | 69978-82-1

• 物质功能分类: 天然产物 - 倍半萜
• 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
• 中文名称: 异木香酸
• 英文名称: isocostic acid
• 英文别名: γ-costic acid；2-[(2R,4aR)-4a,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• CAS: 69978-82-1
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: SGZOYHLQNUSAIL-IUODEOHRSA-N

物化性质

• 沸点：
  374.0±11.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异木香酸 生成 异肋骨甲酯
  参考文献：
  名称：

  SANZ, JUAN F.;FALCO, ENRIQUE;MARCO, J. ALBERTO, J. NATUR. PROD., 53,(1990) N, C. 940-945

  摘要：

  DOI：
• 作为产物：
  描述：

  4-hydroxy-11(13)-eudesmen-12-oic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.08h， 以98 mg的产率得到异木香酸
  参考文献：
  名称：

  Sesquiterpenes from Tessaria absinthioides

  摘要：

  DOI：

  10.1016/s0031-9422(96)00590-0

文献信息

• Germacrenes from fresh costus roots
  作者：Jan-Willem de Kraker、Maurice C.R Franssen、Aede de Groot、Toshiro Shibata、Harro J Bouwmeester

  DOI：10.1016/s0031-9422(01)00291-6

  日期：2001.10

  (-)-beta-elemene, (-)-elema-1,3,11(13)-trien-12-ol, (-)-elema-1,3,11(13)-trien-12-al, and elema-1,3,11(13)-trien-12-oic acid respectively, in addition to small amounts of their diastereomers. Acid induced cyclisation of the germacrenes yields selinene, costol, costal, and costic acid respectively. It is highly probable that the elemenes reported in literature for costus root oil are artefacts.

  从新鲜木香根 (Saussurea lappa) 中分离出四种以前被证明是倍半萜内酯生物合成中间体的胚芽烯。(+)-germacrene A,germacra-1(10),4,11(13)-trien-12-ol,germacra-1(10),4,11(13)-trien-12-al的结构，和germacra-1(10),4,11(13)-trien-12-oic acid 是通过光谱数据和化学转化的组合推导出来的。这些化合物的加热产生 (-)-β-榄香烯、(-)-elema-1,3,11(13)-trien-12-ol, (-)-elema-1,3,11(13)-trien -12-al 和 elema-1,3,11(13)-trien-12-oic 酸，以及少量的非对映异构体。锗烯的酸诱导环化分别产生硒烯、木香醇、肋骨和木香酸。很有可能文献中报道的木香油的榄香烯是人工制品。
• A simple synthesis of α-Costic acid analogue with antibacterial potential, DFT and molecular docking
  作者：F. E. Maaghloud、F. Moukhfi、A. Abdou、N. Chadli、A. Aboulmouhajir、H. Elmakssoudi、A. El Hakmaoui、J. Jamal Eddine、M. Akssira、M. Dakir

  DOI：10.1080/14786419.2022.2144851

  日期：——

  Natural products extracted from plants has been recognized as the most efficient starting materials to synthesize new derivatives of medicinal interest. Our research focuses on the isolation and ch...

  从植物中提取的天然产物已被认为是合成具有药用价值的新衍生物的最有效的起始材料。我们的研究重点是隔离和...
• Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines
  作者：Leticia G. León、Osvaldo J. Donadel、Carlos E. Tonn、José M. Padrón

  DOI：10.1016/j.bmc.2009.07.053

  日期：2009.9.1

  A series of analogs were synthesized in a straightforward manner from naturally available sesquiterpenes ilicic acid and tessaric acid. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, HBL-100, HeLa, SW1573, T-47D and WiDr. The most potent analog induced considerably growth inhibition in the range 1.9-4.5 mu M. Cell cycle studies for tessaric acid derivatives indicated a prominent arrest of the cell cycle at the G(2)/M phase. Damage to the cells was permanent as determine by the so called 24+24 drug schedule. (C) 2009 Elsevier Ltd. All rights reserved.
• Cruz, Raymundo; Martinez, Rosa M., Australian Journal of Chemistry, 1982, vol. 35, # 2, p. 451 - 456
  作者：Cruz, Raymundo、Martinez, Rosa M.

  DOI：——

  日期：——
• Gastric cytoprotective activity of ilicic aldehyde: Structure–activity relationships
  作者：Osvaldo J. Donadel、Eduardo Guerreiro、Alejandra O. María、Graciela Wendel、Ricardo D. Enriz、Oscar S. Giordano、Carlos E. Tonn

  DOI：10.1016/j.bmcl.2005.05.053

  日期：2005.8

  A series of sesquiterpene compounds possessing both eudesmane and eremophilane skeletons were tested as gastric cyto-protective agents on male Wistar rats. The presence of an alpha,beta-unsaturated aldehyde on the C-7 side chain together with a hydroxyl group at C-4 is the requirement for the observed antiulcerogenic activity. In an attempt to establish new molecular structural requirements for this gastric cytoprotective activity, a structure-activity study was performed. (c) 2005 Elsevier Ltd. All rights reserved.