1-(3,4-二羟基-5-甲氧基苯基)乙酮 | 3934-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,4-二羟基-5-甲氧基苯基)乙酮
• 英文名称: 5-hydroxyacetovanillone
• 英文别名: 3',4'-dihydroxy-5'-methoxyacetophenone；1-(3,4-dihydroxy-5-methoxyphenyl)-ethan-1-one；4,5-Dihydroxy-3-methoxy-acetophenon；5-Hydroxy-aceto-guaiacon；3,4-Dihydroxy-5-methoxy-acetophenon；Acetophenone, 3,4-dihydroxy-5-methoxy-；1-(3,4-dihydroxy-5-methoxyphenyl)ethanone
• CAS: 3934-89-2
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: APWNPKIBUXZTOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  1-(3,4-二羟基-5-甲氧基苯基)乙酮 、 S-adenosyl-L-methionine 在 crude enzymatic extracts from TX₁ tobacco (Nicotiana tabacum L_. cv. Xanthi) cells collected 72 h after MeJa treatment 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 乙酰丁香酮
  参考文献：
  名称：

  Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures

  摘要：

  Acetosyringone (3',5'-dimethoxy-4'-hydroxyacetophenone) is a well-known and very effective inducer of the virulence genes of Agrobacterium tumefaciens but the precise pathway of its biosynthesis in plants is still unknown. We have used two tobacco cell lines, cultured in suspension and exhibiting different patterns of accumulation of acetosyringone in their culture medium upon treatment with methyl jasmonate, to study different steps of acetosyringone biosynthesis. In the two cell lines studied, treatment with 100 mu M methyl jasmonate triggered a rapid and transient increase in acetovanillone synthase activity followed by a progressive increase in S-adenosyl-L-methionine: 5-hydroxyacetovanillone 5-O-methyltransferase activity which paralleled the rise in acetosyringone concentration in the culture medium. This O-methyltransferase displayed. Michaelis-Menten kinetics with an apparent K-m value of 18 mu M for 5-hydroxyacetovanillone and its activity was magnesium-independent. Its molecular mass was estimated by gel permeation on an FPLC column and was found to be of ca. Si kDa. 5-Hydroxyacetovanillone was the best substrate among the different o-diphenolic compounds tested as methyl acceptors in the O-methyltransferase assay. No formation of 5-hydroxyacetovanillone could be detected in vitro from 5-hydroxyferuloyl-CoA and NAD in the extracts used to measure acetovanillone synthase activity, indicating that 5-hydroxyacetovanillone is probably formed by direct hydroxylation of acetovanillone rather than by beta-oxidation of 5-hydroxyferulic acid. Taken together our results strongly support the hypothesis that acetosyringone biosynthesis in tobacco proceeds from feruloyl-CoA via acetovanillone and 5-hydroxyacetovanillone. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.12.013
• 作为产物：
  描述：

  1-(4-羟基-3-碘-5-甲氧基苯基)乙酮 在 copper(ll) sulfate pentahydrate 、 sodium hydroxide 作用下， 以31%的产率得到1-(3,4-二羟基-5-甲氧基苯基)乙酮
  参考文献：
  名称：

  Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures

  摘要：

  Acetosyringone (3',5'-dimethoxy-4'-hydroxyacetophenone) is a well-known and very effective inducer of the virulence genes of Agrobacterium tumefaciens but the precise pathway of its biosynthesis in plants is still unknown. We have used two tobacco cell lines, cultured in suspension and exhibiting different patterns of accumulation of acetosyringone in their culture medium upon treatment with methyl jasmonate, to study different steps of acetosyringone biosynthesis. In the two cell lines studied, treatment with 100 mu M methyl jasmonate triggered a rapid and transient increase in acetovanillone synthase activity followed by a progressive increase in S-adenosyl-L-methionine: 5-hydroxyacetovanillone 5-O-methyltransferase activity which paralleled the rise in acetosyringone concentration in the culture medium. This O-methyltransferase displayed. Michaelis-Menten kinetics with an apparent K-m value of 18 mu M for 5-hydroxyacetovanillone and its activity was magnesium-independent. Its molecular mass was estimated by gel permeation on an FPLC column and was found to be of ca. Si kDa. 5-Hydroxyacetovanillone was the best substrate among the different o-diphenolic compounds tested as methyl acceptors in the O-methyltransferase assay. No formation of 5-hydroxyacetovanillone could be detected in vitro from 5-hydroxyferuloyl-CoA and NAD in the extracts used to measure acetovanillone synthase activity, indicating that 5-hydroxyacetovanillone is probably formed by direct hydroxylation of acetovanillone rather than by beta-oxidation of 5-hydroxyferulic acid. Taken together our results strongly support the hypothesis that acetosyringone biosynthesis in tobacco proceeds from feruloyl-CoA via acetovanillone and 5-hydroxyacetovanillone. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.12.013

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic‐Liquid Treatment
  作者：Amel Majira、Blandine Godon、Laurence Foulon、Jacinta C. Putten、Laurent Cézard、Marina Thierry、Florian Pion、Anne Bado‐Nilles、Pascal Pandard、Thangavelu Jayabalan、Véronique Aguié‐Béghin、Paul‐Henri Ducrot、Catherine Lapierre、Guy Marlair、Richard J. A. Gosselink、Stephanie Baumberger、Betty Cottyn

  DOI：10.1002/cssc.201901916

  日期：2019.11.8

  A grass soda technical lignin (PB1000) underwent a process combining solvent fractionation and treatment with an ionic liquid (IL), and a comprehensive investigation of the structural modifications was performed by using high-performance size-exclusion chromatography, 31 P NMR spectroscopy, thioacidolysis, and GC-MS. Three fractions with distinct reactivity were recovered from successive ethyl acetate

  草酸工业木质素（PB1000）经过溶剂分馏并用离子液体（IL）处理的过程，并通过使用高性能尺寸排阻色谱，31 P NMR光谱，硫代酸解进行了结构修饰的综合研究。和GC-MS。从连续的乙酸乙酯（EA），丁酮和甲醇提取物中回收了具有不同反应性的三个馏分。平行地，获得了缺少EA提取物的级分。通过使用常规加热或微波辐射，用甲基咪唑鎓溴化物（[HMIM] Br）处理样品。该处理使我们能够溶解28％的EA不溶级分，并由于解聚和脱甲基作用而在所有级分中产生了额外的游离酚。通过2，2-二苯基-1-吡啶并肼基（DPPH。）自由基清除测试证明了组合方法在抗氧化剂性能方面的优势。这项研究综合了与IL安全性相关的更多数据和环境因素，为与商业抗氧化剂竞争的酚醛低聚物的可持续生产铺平了道路。
• METHOD FOR THE SYNTHESIS OF ANTHOCYANINS
  申请人：Bakstad Einar

  公开号：US20090111975A1

  公开（公告）日：2009-04-30

  The present invention relates to methods of preparing anthocyanins, and methods of preparing precursors of anthocyanins. The methods utilise a coupling reaction between a sugar and a suitable electrophilic precursor to form Eastern half intermediates that are then reacted with Western half intermediates to form the target anthocyanins. Some Eastern half intermediates and electrophilic precursors also form part of the invention.

  本发明涉及制备花青素的方法，以及制备花青素前体的方法。该方法利用糖与适当的亲电前体之间的偶联反应形成东半部分中间体，然后将其与西半部分中间体反应以形成目标花青素。一些东半部分中间体和亲电前体也是本发明的一部分。
• Modulators of ATP-Binding Cassette Transporters
  申请人：Hadida Ruah Sara S.

  公开号：US20110060024A1

  公开（公告）日：2011-03-10

  Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明的化合物及其药学上可接受的组合物，可用作ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜导电调节因子（“CFTR”）。本发明还涉及使用本发明的化合物治疗ABC转运蛋白介导的疾病的方法。