(2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl]-3-methylpenta-2,4-dienoic acid | 1584128-19-7

• 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: (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl]-3-methylpenta-2,4-dienoic acid
• 英文别名: pyrenophoric acid；(2Z,4E)-5-[(1S,3S,4R,6R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl]-3-methylpenta-2,4-dienoic acid
• CAS: 1584128-19-7
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: MSGLVYRESMKEPC-ZCJFAIRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl]-3-methylpenta-2,4-dienoic acid 以 甲醇 、 乙醚 为溶剂， 以1.5 mg的产率得到pyrenophoric acid methyl ester
  参考文献：
  名称：

  Pyrenophoric Acid, a Phytotoxic Sesquiterpenoid Penta-2,4-dienoic Acid Produced by a Potential Mycoherbicide,Pyrenophora semeniperda

  摘要：

  A new phytotoxic sesquiterpenoid penta-2,4-dienoic acid, named pyrenophoric acid, was isolated from solid wheat seed culture of Pyrenophora semeniperda, a fungal pathogen proposed as a mycoherbicide for biocontrol of cheatgrass (Bromus tectorum) and other annual bromes. These 1 bromes are serious weeds in winter cereals and also on temperate semiarid rangelands. Pyrenophoric acid was characterized as (2Z,4E)-5-[(7S,9S,10R,12R)-3,4-dihydroxy-2,2,6-trimethylcyclohexyl)]-3-methylpenta-2,4-dienoic acid by spectroscopic and chemical methods. The relative stereochemistry of pyrenophoric acid was assigned using H-1,H-1 couplings and NOESY experiments, while its absolute configuration was determined by applying the advanced Mosher's method. Pyrenophoric acid is structurally quite closely related to the plant growth regulator abscisic acid. When bioassayed in a cheatgrass coleoptile elongation test at 10(-3) M, pyrenophoric acid showed strong phytotoxicity, reducing coleoptile elongation by 51% relative to the control. In a mixture at 10(-4) M, its negative effect on coleoptile elongation was additive with that of cytochalasin B, another phytotoxic compound found in the wheat seed culture extract of this fungus, demonstrating that the extract toxicity observed in earlier studies was due to the combined action of multiple phytotoxic compounds.

  DOI：

  10.1021/np4009915