4-hydroxy-6-(2-oxopropyl)pyran-2-one | 10310-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-hydroxy-6-(2-oxopropyl)pyran-2-one
• 英文别名: 6-acetonyl-4-hydroxy-2-pyrone；4-Hydroxy-6-acetonyl-α-pyron；Tetraessigsaeurelacton；4-Hydroxy-6-(2-oxopropyl)-2H-pyran-2-one
• CAS: 10310-07-3
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: STVPTNMFKNDFLX-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  316.4±42.0 °C(Predicted)
• 密度：
  1.347±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  丙二酰辅酶A-钠盐 在 potassium phosphate buffer 、 乙二胺四乙酸 、 G₂₀₇W mutated octaketide synthase 作用下， 反应 18.0h， 生成 4-hydroxy-6-(2-oxopropyl)pyran-2-one
  参考文献：
  名称：

  植物聚酮化合物的工程生物合成：生产八肽的植物 III 型聚酮化合物合成酶中的链长控制

  摘要：

  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

  DOI：

  10.1021/ja053945v

文献信息

• Preparation of enol lactones of 3,5,7-triketo and 3,5,7,9-tetraketo acids by the condensation of 4,6-dimethoxy-2-pyrone with anions of mono- and diketones
  作者：John A. Ray、Thomas M. Harris

  DOI：10.1016/s0040-4039(00)87236-6

  日期：1982.1

  Condensation of the anions of acetone, acetophenone, acetylacetone and benzoylacetone with 4,6-dimethoxy-2-pyrone afforded good yields of the corresponding 6 substituted 4-methoxy-2-pyrones which were converted to the 4-hydroxy analogs by demethylation with iodotrimethylsilane.

  丙酮，苯乙酮，乙酰丙酮和苯甲酰丙酮的阴离子与4,6-二甲氧基-2-吡喃酮的缩合得到相应的6个取代的4-甲氧基-2-吡喃酮的良好收率，将其通过碘代三甲基硅烷脱甲基转化为4-羟基类似物。 。
• Exploiting the Reaction Flexibility of a Type III Polyketide Synthase through in Vitro Pathway Manipulation
  作者：Jae-Cheol Jeong、Aravind Srinivasan、Sabine Grüschow、Horacio Bach、David H. Sherman、Jonathan S. Dordick

  DOI：10.1021/ja0441559

  日期：2005.1.1

  synthesis of the pentaketide flaviolin and its dimeric derivative, and a wide range of pyrones and their coupled derivatives with flaviolin, as well as their halogenated derivatives. The addition of acyl-CoA oxidase to the pathway prior to the polyketide synthase resulted in unsaturated pyrone side chains, further broadening the product spectrum that can be achieved. The approach developed in this work

  在体外构建了一个合成代谢途径，包括来自天蓝色链霉菌的 III 型聚酮化合物合酶和来自大豆和烟熏蓝藻（氯过氧化物酶）的过氧化物酶。这导致合成了五肽黄素及其二聚衍生物，以及广泛的吡喃酮及其与黄素的偶联衍生物，以及它们的卤化衍生物。在聚酮合酶之前将酰基辅酶A氧化酶添加到途径中导致不饱和的吡喃酮侧链，进一步拓宽了可以实现的产物谱。因此，这项工作中开发的方法为在复杂天然产物衍生物的合成中利用生物催化提供了一种新模型。
• A Novel Class of Plant Type III Polyketide Synthase Involved in Orsellinic Acid Biosynthesis from Rhododendron dauricum
  作者：Futoshi Taura、Miu Iijima、Eriko Yamanaka、Hironobu Takahashi、Hiromichi Kenmoku、Haruna Saeki、Satoshi Morimoto、Yoshinori Asakawa、Fumiya Kurosaki、Hiroyuki Morita

  DOI：10.3389/fpls.2016.01452

  日期：——

  produces daurichromenic acid, the anti-HIV meroterpenoid consisting of sesquiterpene and orsellinic acid (OSA) moieties. To characterize the enzyme responsible for OSA biosynthesis, a cDNA encoding a novel polyketide synthase (PKS), orcinol synthase (ORS), was cloned from young leaves of R. dauricum. The primary structure of ORS shared relatively low identities to those of PKSs from other plants, and the active

  杜鹃花杜鹃花产生杜里铬酸，一种抗艾滋病毒的类萜，由倍半萜和奥数酸（OSA）部分组成。为了表征负责OSA生物合成的酶，从道夫幼叶中克隆了编码新型聚酮合酶（PKS），蓖麻酚合酶（ORS）的cDNA。ORS的一级结构与其他植物的PKS具有较低的同一性，并且ORS的活性位点具有独特的氨基酸组成。细菌表达的重组ORS接受了乙酰辅酶A作为优选的起始底物，并生产了鸟脚酚作为主要反应产物，以及包括OSA在内的四种次要产物。在这项研究中鉴定出的ORS是第一个生成PKS的植物PKS，该PKS产生乙酸盐衍生的芳族四酮类化合物，例如牛油酚和OSA。有趣的是，
• Studies on the resorcylates: biomimetic total syntheses of (+)-montagnetol and (+)-erythrin
  作者：Jean-François Basset、Colin Leslie、Dieter Hamprecht、Andrew J.P. White、Anthony G.M. Barrett

  DOI：10.1016/j.tetlet.2009.11.134

  日期：2010.2

  6-(2,4-Dioxopentyl)-2,2-trimethyl-4H-1,3-dioxin-4-one on reflux in toluene gave MeCOCH2COCH2 COCH=C=O, which cyclized to 6-(2-oxopropyl)-4-hydroxy-2H-pyrin-2-one or was trapped with alcohols to produce resorcylate esters. The method was used for the synthesis of both enantiomers of montagnetol and erythrin. (c) 2009 Elsevier Ltd. All rights reserved.
• 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.