7-hydroxyoxindole-3-acetic acid | 40660-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-hydroxyoxindole-3-acetic acid
• 英文别名: 7-hydroxy-2-indolinone-3-acetic acid；7-hydroxy-2-oxindole-3-acetic acid；2-(7-hydroxy-2-oxo-1,3-dihydroindol-3-yl)acetic acid
• CAS: 40660-90-0
• 化学式: C₁₀H₉NO₄
• 分子量: 207.186
• InChiKey: RBODBEHKWJZUBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-hydroxyoxindole-3-acetic acid 在 氢气 作用下， 生成 8-hydroxy-1,2,3,4-tetrahydro-2-quinolone-4-carboxylic acid
  参考文献：
  名称：

  Occurrence and metabolism of 7-hydroxy-2-indolinone-3-acetic acid in zea mays

  摘要：

  7-Hydroxy-2-indolinone-3-acetic acid was identified as a catabolite of indole-3-acetic acid in germinating kernels of Zea mays and found to be present in amounts of ca 3.1 nmol/kernel. 7-Hydroxy-2-indolinone-3-acetic acid was shown to be a biosynthetic intermediate between 2-indolinone-3-acetic acid and 7-hydroxy-2-indolinone-3-acetic acid-7'-O-glucoside in both kernels and roots of Zea mays. Further metabolism of 7-hydroxy-2-[5-3H]-indolinone-3-acetic acid-7'-O-glucoside occurred to yield tritiated water plus, as yet, uncharacterized products.

  DOI：

  10.1016/s0031-9422(00)81790-2
• 作为产物：
  描述：

  甲基吲哚-3-乙酸盐 在 甲醇 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 3,4,7,8-四甲基-1,10-菲罗啉 、 双氧水 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.52h， 生成 7-hydroxyoxindole-3-acetic acid
  参考文献：
  名称：

  A short synthesis of the endogenous plant metabolite 7-hydroxyoxindole-3-acetic acid (7-OH-OxIAA) using simultaneous C–H borylations

  摘要：

  Methyl indole-3-acetate undergoes two simultaneous iridium-catalysed borylations to deliver exclusively 2,7-diboronate, with the ligand 3,4,7,8-tetramethyl-1,10-phenanthroline (Me(4)Phen) pivotal in driving the diborylation to completion. Subsequent oxidation-hydrolysis of the diboronate provides methyl 7-hydroxyoxindole-3-acetate which upon hydrolysis of the ester delivers 7-OH-OxIAA, an antioxidant, endogenous metabolite of indole-3-acetic acid found in various types of corn. This route has an overall yield of 50%, involves a single chromatographic purification and is an efficient alternative to existing syntheses, made possible by executing simultaneous oxidations at the indole C2 and C7 sites. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.104

文献信息

• Antioxidative Activities of Oxindole-3-acetic Acid Derivatives from Supersweet Corn Powder
  作者：Naoki MIDOH、Akihito TANAKA、Makiko NAGAYASU、Chie FURUTA、Katsuya SUZUKI、Takeshi ICHIKAWA、Takashi ISOMURA、Kenzo NOMURA

  DOI：10.1271/bbb.100124

  日期：2010.9.23

  The components contributing to the antioxidative activity of supersweet corn powder (SSCP), which is commonly used in corn soup and snacks in Japan, were clarified and the effects investigated. 7-(O-β-Glucosyloxy)oxindole-3-acetic acid (GOA) was found to be the component most strongly contributing to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity of the 80% ethanol extract of SSCP

  澄清了在日本玉米汤和小吃中常用的超甜玉米粉（SSCP）的抗氧化活性成分，并研究了其效果。发现7-（O-β-葡糖基氧基）吲哚-3-乙酸（GOA）是最有力地促进80％乙醇的1,1-二苯基-2-吡啶并肼基（DPPH）自由基清除活性的成分证实了SSCP的提取物及其糖苷配基7-羟基-羟吲哚-3-乙酸（HOA）的存在。GOA和HOA分别对80％的SSCP乙醇提取物的DPPH自由基清除活性贡献了35.1％和10.5％。口服给予500和1500 mg / kg的HOA的小鼠血浆中的硫代巴比妥酸反应性物质（TBARS）的水平显着低于溶媒治疗的对照组（p <0.05）。
• Oxidative Reaction of Oxindole-3-acetic Acids
  作者：Toshio NIWA、Sayuri ISHII、Atsushi HIRAMATSU、Toshihiko OSAWA

  DOI：10.1271/bbb.67.1870

  日期：2003.1

  The oxindole-3-acetic acids, oxidative metabolites of indole-3-acetic acid, were isolated from a byproduct of a corn starch manufacturing plant, and were further converted to the 3-hydroxyl derivatives in the presence of metal ion. The mechanical study was followed by a chemical analysis including other byproducts, and suggested the presence of an intermediate that had a radical at the C-3 position of oxindole-3-acetic acids.

  从玉米淀粉生产厂的副产品中分离出了吲哚-3-乙酸的氧化代谢产物--吲哚-3-乙酸，并在金属离子存在下进一步转化为 3-羟基衍生物。机械研究之后还进行了包括其他副产品在内的化学分析，结果表明在吲哚-3-乙酸的 C-3 位上存在一种带有自由基的中间体。
• Lewer, Paul, Journal of the Chemical Society. Perkin transactions I, 1987, p. 753 - 758
  作者：Lewer, Paul

  DOI：——

  日期：——
• US5919998A
  申请人：——

  公开号：US5919998A

  公开（公告）日：1999-07-06
• US6489541B1
  申请人：——

  公开号：US6489541B1

  公开（公告）日：2002-12-03