3-(2-pyron-6-yl)propanoic acid | 183960-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(2-pyron-6-yl)propanoic acid
• 英文别名: 3-(6-Oxopyran-2-yl)propanoic acid
• CAS: 183960-17-0
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: HZIVCFVTYCOEQE-UHFFFAOYSA-N

物化性质

• 沸点：
  412.2±28.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-(2-pyron-6-yl)propanoic acid 以 乙醚 、 乙酸乙酯 为溶剂， 生成 methyl 3-(2-pyron-6-yl)propanoate
  参考文献：
  名称：

  Biotransformation of 6-Pentyl-2-pyrone by Botrytis cinerea in Liquid Cultures

  摘要：

  Metabolism of 6-pentyl-2-pyrone (6PP) added at rates up to 120 mu g/mL to liquid Botrytis cinerea cultures produced the previously unreported compounds 3-(2-pyron-6-yl)propanoic acid and 5-(2-pyrong-6-yl)pentanoic acid. Another metabolite was identified tentatively from its mass spectrum as either 5-(2-pyron-6-yl)pentanol or 5-(2-pyron-6-yl)pentan-2-ol. B. cinerea hyphae remained viable with 6PP at 200 mu g/mL, but their growth was suppressed at this concentration. Pyrone-containing metabolites were not observed in all systems to which 6PP had been added, but were formed in both hyphal development and sporulating phases of growth. These metabolites were stable in the presence of actively growing B. cinerea cultures and did not appear to alter fungal growth. It is proposed that the changes to the alkyl side chain in the metabolites reduced their lipophilicity and ability to permeate cell membranes relative to the parent compound, thus reducing their toxicity to the fungus.

  DOI：

  10.1021/jf9603644
• 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.
• Biotransformation of 6-Pentyl-2-pyrone by <i>Botrytis </i><i>cinerea </i>in Liquid Cultures
  作者：Philip R. Poole、Giles Whitaker

  DOI：10.1021/jf9603644

  日期：1997.1.1

  Metabolism of 6-pentyl-2-pyrone (6PP) added at rates up to 120 mu g/mL to liquid Botrytis cinerea cultures produced the previously unreported compounds 3-(2-pyron-6-yl)propanoic acid and 5-(2-pyrong-6-yl)pentanoic acid. Another metabolite was identified tentatively from its mass spectrum as either 5-(2-pyron-6-yl)pentanol or 5-(2-pyron-6-yl)pentan-2-ol. B. cinerea hyphae remained viable with 6PP at 200 mu g/mL, but their growth was suppressed at this concentration. Pyrone-containing metabolites were not observed in all systems to which 6PP had been added, but were formed in both hyphal development and sporulating phases of growth. These metabolites were stable in the presence of actively growing B. cinerea cultures and did not appear to alter fungal growth. It is proposed that the changes to the alkyl side chain in the metabolites reduced their lipophilicity and ability to permeate cell membranes relative to the parent compound, thus reducing their toxicity to the fungus.