6-Dodecyl-4-hydroxypyran-2-one | 1446208-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-Dodecyl-4-hydroxypyran-2-one
• CAS: 1446208-89-4
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: ATLWMEMDAQGJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  十三酸 、 乙酰辅酶A 在 3,3,3-膦三基三丙酸 、 broad chain fatty acid:CoA thiolase from Escherichia coli 、 long chain fatty acid:CoA ligase from Escherichia coli 、 medium chain fatty acid:CoA ligase from Escherichia coli 、 5’-三磷酸腺苷 、 magnesium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 生成 6-Dodecyl-4-hydroxypyran-2-one
  参考文献：
  名称：

  10.1002/anie.202206851

  摘要：

  AbstractNaturally occurring α‐pyrones with biological activities are mostly synthesised by polyketide synthases (PKSs) via iterative decarboxylative Claisen condensation steps. Remarkably, we found that some enzymes related to the fatty acid β‐oxidation pathway in Escherichia coli, namely the CoA ligase FadD and the thiolases FadA and FadI, can synthesise styrylpyrones with phenylpropionic acids in vivo. The two thiolases directly utilise acetyl‐CoA as an extender unit for carbon‐chain elongation through a non‐decarboxylative Claisen condensation, thus making the overall reaction more efficient in terms of carbon and energy consumption. Moreover, using a cell‐free approach, different styrylpyrones were synthesised in vitro. Finally, targeted feeding experiments led to the detection of styrylpyrones in other species, demonstrating that the intrinsic ability of the β‐oxidation pathway allows for the synthesis of such molecules in bacteria, revealing an important biological feature hitherto neglected.

  DOI：

  10.1002/anie.202206851

文献信息

• A type III polyketide synthase from Rhizobium etli condenses malonyl CoAs to a heptaketide pyrone with unusually high catalytic efficiency
  作者：Marimuthu Jeya、Tae-Su Kim、Manish Kumar Tiwari、Jinglin Li、Huimin Zhao、Jung-Kul Lee

  DOI：10.1039/c2mb25347j

  日期：——

  A novel type III polyketide synthase (RePKS) from Rhizobium etli produced a heptaketide pyrone using acetyl-CoA and six molecules of malonyl-CoA. Its catalytic efficiency (kcat/Km = 5230 mM−1 min−1) for malonyl CoA was found to be the highest ever reported. Molecular dynamics studies revealed the unique features of RePKS.

  一种来自根瘤菌（Rhizobium etli）的新型 III 型多酮合成酶（RePKS）利用乙酰-CoA 和六分子丙二酰-CoA 生成了一种七酮吡咯烷酮。它对丙二酰 CoA 的催化效率（kcat/Km = 5230 mM-1 min-1）是迄今所报道的最高的。分子动力学研究揭示了 RePKS 的独特之处。
• [DE] VERWENDUNG VON ZUSAMMENSETZUNGEN ENTHALTEND 4-HYDROXY-2-PYRONE ZUR STABILISIERUNG VON HALOGENHALTIGEN ORGANISCHEN KUNSTSTOFFEN<br/>[EN] USE OF COMPOSITIONS CONTAINING 4-HYDROXY-2-PYRONES FOR STABILISING ORGANIC PLASTICS CONTAINING HALOGEN<br/>[FR] UTILISATION DE COMPOSITIONS CONTENANT DES 4-HYDROXY-2-PYRONES POUR LA STABILISATION DE PLASTIQUES ORGANIQUES HALOGENES
  申请人：COGNIS DEUTSCHLAND GMBH

  公开号：WO2004018552A1

  公开（公告）日：2004-03-04

  Zusammensetzungen enthaltend mindestens ein 4-Hydroxy-2-pyron der Formel (I) worin der Rest R Wasserstoff, einen gegebenenfalls substituierten Alkylrest mit insgesamt 1 bis 18 C-Atomen oder einen gegebenenfalls substituierten Arylrest mit insgesamt 6 bis 24 C-Atomen bedeutet, eignen sich zur Stabilisierung von halogenhaltigen organischen Kunststoffen, insbesondere PVC, gegen thermischen und/oder photochemischen Abbau.