1,2-二羟基-3-甲基蒽醌 | 602-63-1

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,2-二羟基-3-甲基蒽醌
• 英文名称: 1,2-dihydroxy-3-methyl-anthraquinone
• 英文别名: 3-methylalizarin；1,2-dihydroxy-3-methyl-9,10-anthraquinone；1,2-Dihydroxy-3-methyl-anthrachinon；1,2-Dihydroxy-3-methylanthraquinone；1,2-dihydroxy-3-methylanthracene-9,10-dione
• CAS: 602-63-1
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: QPAGCTACMMYJIO-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C
• 沸点：
  460.3±45.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  储存条件：2-8°C，避光，惰性气体保护。

反应信息

• 作为反应物：
  描述：

  1,2-二羟基-3-甲基蒽醌 在 磺酰氯 、 碘 、 硝基苯 作用下， 生成 1-chloro-3,4-dihydroxy-2-methyl-anthraquinone
  参考文献：
  名称：

  Metasomatic coronas around hornblendite xenoliths in granulite facies marble, Ivrea zone, N Italy. II: Oxygen isotope patterns

  摘要：

  Up to 20-cm-wide metasomatic reaction bands formed coronas around hornblendite xenoliths in a marble matrix during high grade metamorphism in the Ivrea zone. The coronas are comprised of an innermost monomineralic clinopyroxene layer, a garnet-clinopyroxene layer and an outermost scapolite-clinopyroxene layer. The oxygen isotope composition of the original hornblendite core is 7%,, relative to V-SMOW and the oxygen isotope composition of the marble matrix is 19.7 parts per thousand. The oxygen isotope transition across the corona is represented by a diffusion front with a step discontinuity at the inner margin of the corona. The systematics of the inter-mineral fractionations indicates preservation of the oxygen isotope compositions from high temperatures and maintenance of grain-scale oxygen isotope equilibrium during corona formation. The oxygen isotope pattern is interpreted in terms of a moving boundary diffusion problem. The growing reaction band and the reactant hornblendite and marble represent a total of five media with different transport properties and moving separation surfaces. Bulk oxygen diffusion was at least three orders of magnitude faster then expected from volume diffusion, suggesting that transport was enhanced by relatively fast diffusion along grain boundaries. Oxygen diffusivities in the individual layers correlate with the oxygen volume diffusivities in the major constituent minerals of the respective layers, suggesting mineralogical control on bulk oxygen diffusion.

  DOI：

  10.1007/s004100100256
• 作为产物：
  描述：

  2-甲基蒽醌 在 硫酸 作用下， 生成 1,2-二羟基-3-甲基蒽醌
  参考文献：
  名称：

  Fischer,O., Chemische Berichte, 1875, vol. 8, p. 675

  摘要：

  DOI：

文献信息

• Synthesis and Activity of Substituted Anthraquinones against a Human Filarial Parasite, <i>Brugia </i><i>m</i><i>alayi</i>
  作者：Mugunthu R. Dhananjeyan、Youli P. Milev、Michael A. Kron、Muraleedharan G. Nair

  DOI：10.1021/jm0492655

  日期：2005.4.1

  reported anthraquinones from daylily roots with potent activity against pathogenic trematode Schistosoma mansoni. Here we report the synthesis of novel anthraquinones A-S and their antifilrarial activity. Anthraquinones A-S were synthesized by a single-step Friedel-Crafts acylation reaction between phthalic anhydrides and substituted benzenes. The antifilarial properties of these synthetic anthraquinones were

  淋巴丝虫病（elephantiasis）是由寄生线虫Wuchereria bancrofti和Brugia malayi引起的全球性公共卫生问题。我们以前曾报道过黄花菜根中的蒽醌具有对病原性曼氏血吸虫的有效活性。在这里，我们报告新型蒽醌AS的合成及其抗丝活性。通过邻苯二甲酸酐和取代苯之间的一步式Friedel-Crafts酰化反应合成蒽醌AS。测试了这些合成蒽醌的抗丝虫特性，以防微丝虫以及马来芽孢杆菌的成年雄性和雌性蠕虫。活性最强的蒽醌为K，在浓度为5 ppm的微丝aria虫和成年雄性和雌性蠕虫中，分别在1、5和3天内显示100％的死亡率。阿苯达唑 当前用于治疗寄生虫感染的口服药物被用作阳性对照。蒽醌的甲基化产物不影响微丝aria。经治疗的成年女性寄生虫的组织学检查显示，大多数蒽醌对子宫内胚胎造成了明显影响。
• Novel anthraquinones and process for the preparation and method of use thereof
  申请人：Nair G. Muraleedharan

  公开号：US20050267307A1

  公开（公告）日：2005-12-01

  A process for the preparation of hydroxyl substituted anthraquinones is described. The process couples a phthalic anhydride (substituted or unsubstituted) to benzene ring moiety substituted with at least two hydroxyl groups. Remaining hydroxy groups were converted to methoxy groups in some anthraquinones. The compounds are particularly useful for the treatment of parasitic diseases. Also, a method of treating or preventing malaria, filariasis schistosomiasis and other parasitic diseases using anthraquinones.

  描述了一种制备羟基取代蒽醌的方法。该方法将邻苯二甲酸酐（取代或未取代）与至少有两个羟基取代的苯环部分偶联。在一些蒽醌中，剩余的羟基被转化为甲氧基基团。这些化合物特别适用于治疗寄生虫病。此外，还提供了一种使用蒽醌治疗或预防疟疾、丝虫病和血吸虫病等寄生虫病的方法。
• Mitter; Sen, Journal of the Indian Chemical Society, 1928, vol. 5, p. 637
  作者：Mitter、Sen

  DOI：——

  日期：——
• Lovie; Thomson, Journal of the Chemical Society, 1959, p. 4139
  作者：Lovie、Thomson

  DOI：——

  日期：——
• Mitter; Pal, Journal of the Indian Chemical Society, 1930, vol. 7, p. 259,261
  作者：Mitter、Pal

  DOI：——

  日期：——