5-(2-pyron-6-yl)pentan-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(2-pyron-6-yl)pentan-1-ol
• 英文别名: 6-(5-Hydroxypentyl)pyran-2-one
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: MIGMOZQMTSKLRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-戊基-2H-吡喃-2-酮 在 casein hydrolysate 、 葡萄糖 、 Botrytis cinerea 、 盐酸硫胺 、 酒石酸 作用下， 反应 696.0h， 以12 mg的产率得到5-(2-pyron-6-yl)pentanoic acid
  参考文献：
  名称：

  Microbial Transformation of the Trichoderma Metabolite 6-n-Pentyl-2H-pyran-2-one

  摘要：

  Biotransformation of the antifungal Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) (1) by Botrytis cinerea generated the previously reported 3-(2-pyron-6-yl)propionic acid (a) and 5-(2-pyron-6-yl)pentanoic acid (3) and allowed the isolation and characterization of a previously tentatively assigned product as 5-(2-pyron-6-yl)pentan-2-ol (5), plus allowed isolation of a new transformation product identified as 5-(2-pyron-6-yl)pentanoic acid (4). The full NMR spectral assignments of these four compounds are presented here for the first; dime, including some corrections to assignments previously published for 6PAP. Information is also presented on the relative toxicity of 6PAP and its four biotransformation products to B. cinerea, which shows that the metabolism products have reduced toxicity to the pathogenic organism.

  DOI：

  10.1021/np970337n

文献信息

• Biotransformation of the <i>Trichoderma</i> Metabolite 6-<i>n</i>-Pentyl-2<i>H</i>-pyran-2-one (6PAP) by Selected Fungal Isolates
  作者：Janine M. Cooney、Denis R. Lauren

  DOI：10.1021/np980349o

  日期：1999.5.1

  A variety of fungi were tested for their ability to transform the antifungal Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) (1). Three Penicillium isolates, a Sclerotinia isolate, and a Fusarium isolate were all able to rapidly metabolize I and gave mixtures of isomers of monohydroxylated 1 and, in some cases, products resulting from further oxidation to carboxylic acids. Among these products were four previously unidentified metabolites (6, 7, 8, and 9) which were isolated and characterized by NMR spectroscopy. Sphaeropsis sapinea, Ophiostoma quercus, Ophiostoma piceae, a Verticillium sp., and two additional Fusarium isolates were unable to metabolize 1 efficiently.
• Biotransformation of the Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one by cell suspension cultures of Pinus radiata
  作者：Janine M. Cooney、Grant S. Hotter、Denis R. Lauren

  DOI：10.1016/s0031-9422(99)00590-7

  日期：2000.2

  Cell suspension cultures of Pinus radiata metabolize the antifungal Trichoderma secondary metabolite 6-n-pentyl-2H-pyran-2one (6PAP) (1) via hydroxylation of the pentyl side chain. Examination of the culture medium following dosing studies with 1 revealed that 79-85% of this bioactive compound had been metabolised after 144 h. At that time, 34-40% of the metabolized dose was recovered as a series of monohydroxylated isomers of 1, the principal metabolite being 5-(2-pyron-6-yl)pentan-5-ol (7). (C) 2000 Elsevier Science Ltd. AII rights reserved.
• Microbial Transformation of the <i>Trichoderma</i> Metabolite 6-<i>n</i>-Pentyl-2<i>H</i>-pyran-2-one
  作者：Janine M. Cooney、Denis R. Lauren、Philip R. Poole、Giles Whitaker

  DOI：10.1021/np970337n

  日期：1997.12.1

  Biotransformation of the antifungal Trichoderma metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) (1) by Botrytis cinerea generated the previously reported 3-(2-pyron-6-yl)propionic acid (a) and 5-(2-pyron-6-yl)pentanoic acid (3) and allowed the isolation and characterization of a previously tentatively assigned product as 5-(2-pyron-6-yl)pentan-2-ol (5), plus allowed isolation of a new transformation product identified as 5-(2-pyron-6-yl)pentanoic acid (4). The full NMR spectral assignments of these four compounds are presented here for the first; dime, including some corrections to assignments previously published for 6PAP. Information is also presented on the relative toxicity of 6PAP and its four biotransformation products to B. cinerea, which shows that the metabolism products have reduced toxicity to the pathogenic organism.