methyl 4,6-dimethoxy-2-(3,4-dimethoxybenzoyloxy)-salicylate | 25982-03-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: methyl 4,6-dimethoxy-2-(3,4-dimethoxybenzoyloxy)-salicylate
• 英文别名: Methyl-2-veratryloxy-4,6-dimethoxybenzoat；2,4-dimethoxy-6-veratroyloxy-benzoic acid methyl ester；2,4-Dimethoxy-6-veratroyloxy-benzoesaeure-methylester；Methyl 2-(3,4-dimethoxybenzoyl)oxy-4,6-dimethoxybenzoate；methyl 2-(3,4-dimethoxybenzoyl)oxy-4,6-dimethoxybenzoate
• CAS: 25982-03-0
• 化学式: C₁₉H₂₀O₈
• 分子量: 376.363
• InChiKey: HFJDDTICLUPUHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 2-(3,4-二羟基苯甲酰氧基)-4,6-二羟基苯甲酸 生成 methyl 4,6-dimethoxy-2-(3,4-dimethoxybenzoyloxy)-salicylate
  参考文献：
  名称：

  Microbial Degradation of Rutin

  摘要：

  关于芦丁代谢的研究成果相对较少。大鼠口服芦丁后，可在尿液中发现 3,4-二羟基苯乙酸和高香草酸1,2，而在槲皮素存在的情况下，原儿茶酸会在大鼠肾脏匀浆中积累3。

  DOI：

  10.1038/1841145b0

文献信息

• Microbial Degradation of Rutin
  作者：S. HATTORI、I. NOGUCHI

  DOI：10.1038/1841145b0

  日期：1959.10

  COMPARATIVELY little work on the metabolism of rutin has been published. 3,4-dihydroxyphenyl acetic acid and homovanillic acid are found in urine after oral administration of rutin to the rat1,2, and protocatechuic acid accumulates in rat kidney homogenates in the presence of quercetin3.

  关于芦丁代谢的研究成果相对较少。大鼠口服芦丁后，可在尿液中发现 3,4-二羟基苯乙酸和高香草酸1,2，而在槲皮素存在的情况下，原儿茶酸会在大鼠肾脏匀浆中积累3。
• Flavonoid Oxidation by the Radical Generator AIBN:  A Unified Mechanism for Quercetin Radical Scavenging
  作者：Venkat Krishnamachari、Lanfang H. Levine、Paul W. Paré

  DOI：10.1021/jf020045e

  日期：2002.7.1

  nucleophiles revealed that two of the products, namely the substituted benzofuranone (2) and the depside (4), are generated from a common carbocation intermediate. Indirect evidence for the operation of a cyclic concerted mechanism in the formation of the dimeric product (3) is provided. The identification of these products supports the model that the principal site of scavenging reactive oxygen species (ROS)

  槲皮素（五羟基黄酮）与过氧自由基发生剂2,2'-偶氮二异丁腈（AIBN）反应生成的四种氧化的类黄酮衍生物通过色谱法分离，并通过NMR和MS分析鉴定。化合物包括2-（3,4-二羟基苯甲酰基）-2,4,6-三羟基-3（2H）-苯并呋喃酮（2）; 1,3,11a-三羟基-9-（3,5,7-三羟基-4H-1-苯并吡喃-4-基-2-基）-5a-（3,4-二羟基苯基）-5,6,11-六氢-5,6,11-三氧萘并蒽-12-一（3）; 2-（3,4-二羟基苯甲酰氧基）-4,6-二羟基苯甲酸（4）; 和3，4-二羟基苯基乙醛酸甲酯（5）。在不同氢离子浓度和外部亲核试剂下的产物比率表明，两种产物，即取代的苯并呋喃酮（2）和深度（4），是从一种常见的碳正离子中间体生成的。提供了在二聚产物（3）的形成中循环协同机制起作用的间接证据。这些产物的鉴定支持以下模型：槲皮素中清除活性氧（ROS）的主要位点是B环中的邻二羟基取代基以及C环烯烃键。
• Radical-capturing Reaction of 5,7,3',4'-Tetramethylquercetin with the AIBN Radical Initiator
  作者：Takahiro ISHIKAWA、Michiyo TAKAGI、Mamiko KANOU、Shingo KAWAI、Hideo OHASHI

  DOI：10.1271/bbb.64.173

  日期：2000.1

  In order to clarify the mechanism for the radical-capturing reaction which is initiated at the C3-hydroxyl group of flavonols, 5,7,3',4'-tetramethylquercetin (TMQ) was reacted with the 2,2'-azobis-isobutyronitrile (AIBN) radical initiator in benzene. Six products, one depside and its two hydrolytic products, one nitrile adduct, and two others, were isolated from tne reaction mixture, and their structures were determined by instrumental analyses. The quantitative change to the four main products against the reaction time was measured by an HPLC method. The radical-capturing reaction pathway for TMQ with AIBN is proposed from these products and their quantitative changes. The pathway dividing into two clearly reveals that one sub-path formed the depside and its hydrolytic products, while the other formed the nitrile adduct. The reactivity of each two sub-path was nearly the same, different from the case of TMQ and the 2,2'-azobis-2,4-dimethylvaleronitrile (AMVN) radical initiator.

  为了阐明黄酮醇 C3-羟基引发的自由基捕获反应的机理，将 5,7,3',4'-四甲基槲皮素 (TMQ) 与 2,2'-偶氮二异丁腈反应。 (AIBN) 苯中的自由基引发剂。从反应混合物中分离出六种产物，一种缩酚醛及其两种水解产物，一种腈加合物和另外两种，并通过仪器分析确定了它们的结构。采用HPLC法测定四种主要产物随反应时间的定量变化。根据这些产物及其定量变化，提出了 TMQ 与 AIBN 的自由基捕获反应途径。一分为二的路径清楚地表明，一条子路径形成缩酚醛及其水解产物，而另一条子路径形成腈加合物。与TMQ和2,2'-偶氮双-2,4-二甲基戊腈(AMVN)自由基引发剂的情况不同，每两个子路径的反应性几乎相同。
• Mechanism of quercetin oxygenation a possible model for haem degradation
  作者：V. Rajananda、Stanley B. Brown

  DOI：10.1016/s0040-4039(01)82948-8

  日期：1981.1

  Quercetin undergoes base-catalysed oxidative decarbonylation by a mechanism involving only one oxygen molecule, unlike the apparently similar step in haem catabolism, which requires two oxygen molecules.

  槲皮素通过仅涉及一个氧分子的机理进行碱催化的氧化脱羰作用，这与血红素分解代谢中明显相似的步骤（需要两个氧分子）不同。