6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one | 866474-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one
• 英文别名: 6-(2',4'-dihydroxy-6'-methylphenyl)-4-hydroxy-2-pyrone；6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2-pyrone；6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxypyran-2-one
• CAS: 866474-35-3
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: PNZHRLSVSIGZON-UHFFFAOYSA-N

物化性质

• 沸点：
  486.0±45.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  芦荟宁 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one 、 6-(2,4-二羟基-6-甲基苯基)-4-甲氧基吡喃-2-酮
  参考文献：
  名称：

  Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum

  摘要：

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.03.013

文献信息

• Engineered Biosynthesis of Plant Polyketides:  Chain Length Control in an Octaketide-Producing Plant Type III Polyketide Synthase
  作者：Ikuro Abe、Satoshi Oguro、Yoriko Utsumi、Yukie Sano、Hiroshi Noguchi

  DOI：10.1021/ja053945v

  日期：2005.9.1

  The chalcone synthase (CHS) superfamily of type III polyketide synthases (PKSs) produces a variety of plant secondary metabolites with remarkable structural diversity and biological activities (e.g., chalcones, stilbenes, benzophenones, acrydones, phloroglucinols, resorcinols, pyrones, and chromones). Here we describe an octaketide-producing novel plant-specific type III PKS from aloe (Aloe arborescens)

  III 型聚酮化合物合酶 (PKS) 的查尔酮合酶 (CHS) 超家族产生多种具有显着结构多样性和生物活性的植物次级代谢产物（例如查耳酮、芪、二苯甲酮、丙烯、间苯三酚、间苯二酚、吡喃酮和色酮）。在这里，我们描述了一种来自芦荟（Aloe arborescens）的产生八酮化合物的新型植物特异性 III 型 PKS，与其他植物 CHS 超家族酶具有 50-60% 的氨基酸序列同一性。在大肠杆菌中表达的重组酶催化丙二酰辅酶 A 的七次连续脱羧缩合反应，产生芳香族八酮化合物 SEK4 和 SEK4b，这是已知由结构简单的 III 型 PKS 合成的最长的聚酮化合物。令人惊讶的是，定点诱变显示单个残基 Gly207（对应于 CHS' s 活性位点 Thr197) 决定了聚酮链长度和产品特异性。从小到大的取代（G207A、G207T、G207M、G207L、G207F 和 G207W）导致八酮化合物形
• USE OF HETEROLOGOUS EXPRESSED POLYKETIDE SYNTHASE AND SMALL MOLECULE FOLDASES TO MAKE AROMATIC AND CYCLIC COMPOUNDS
  申请人：Danmarks Tekniske Universitet

  公开号：EP3307900A1

  公开（公告）日：2018-04-18
• [EN] USE OF HETEROLOGOUS EXPRESSED POLYKETIDE SYNTHASE AND SMALL MOLECULE FOLDASES TO MAKE AROMATIC AND CYCLIC COMPOUNDS<br/>[FR] UTILISATION DE POLYCÉTIDE SYNTHASE EXPRIMÉE HÉTÉROLOGUE ET DE FOLDASES À PETITES MOLÉCULES POUR PRODUIRE DES COMPOSÉS CYCLIQUES ET AROMATIQUES
  申请人：UNIV DANMARKS TEKNISKE

  公开号：WO2016198623A1

  公开（公告）日：2016-12-15

  A method for producing individual or libraries of tri- to pentadecaketide-derived aromatic compounds of interest by heterologous expression of polyketide synthase and aromatase/cyclase in a recombinant host cell.
• Pyrone polyketides synthesized by a type III polyketide synthase from Drosophyllum lusitanicum
  作者：Aphacha Jindaprasert、Karin Springob、Jürgen Schmidt、Wanchai De-Eknamkul、Toni M. Kutchan

  DOI：10.1016/j.phytochem.2008.03.013

  日期：2008.12

  To isolate cDNAs involved in the biosynthesis of acetate-derived naphthoquinones in Drosophyllum lusitanicum, an expressed sequence tag analysis was performed. RNA from callus cultures was used to create a cDNA library from which 2004 expressed sequence tags were generated. One cDNA with similarity to known type III polyketicle synthases was isolated as full-length sequence and termed DluHKS. The translated polypepticle sequence of DIuHKS showed 51-67% identity with other plant type III PKSs. Recombinant DIuHKS expressed in Escherichia coli accepted acetyl-coenzyme A (CoA) as starter and carried out sequential decarboxylative condensations with malonyl-CoA yielding ot-pyrones from three to six acetate units. However, naphthalenes, the expected products, were not isolated. Since the main compound produced by DIuHKS is a hexaketicle ot-pyrone, and the naphthoquinones in D. lusitanicum are composed of six acetate units, we propose that the enzyme provides the backbone of these secondary metabolites. An involvement of accessory proteins in this biosynthetic pathway is discussed. (c) 2008 Elsevier Ltd. All rights reserved.