1,3,5,7-tetrahydroxy-9,10-anthracenedione | 632-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,3,5,7-tetrahydroxy-9,10-anthracenedione
• 英文别名: anthrachrysin；1,3,5,7-tetrahydroxyanthracene-9,10-dione；1,3,5,7-tetrahydroxyanthraquinone；anthrachrysone；ATCS；1.3.5.7-Tetrahydroxy-anthrachinon-(9.10)；1,3,5,7-Tetrahydroxy-anthrachinon；Anthrachryson
• CAS: 632-82-6
• 化学式: C₁₄H₈O₆
• 分子量: 272.214
• InChiKey: NNAUDJVNWLIGDT-UHFFFAOYSA-N

物化性质

• 熔点：
  360°C
• 沸点：
  375.27°C (rough estimate)
• 密度：
  1.4292 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,5,7-tetrahydroxy-9,10-anthracenedione 生成 1,3,5,7-tetrahydroxy-4,8-dinitro-9,10-dioxo-9,10-dihydro-anthracene-2,6-disulfonic acid
  参考文献：
  名称：

  DE70806

  摘要：

  公开号：
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 硫酸 作用下， 生成 1,3,5,7-tetrahydroxy-9,10-anthracenedione
  参考文献：
  名称：

  Barth; Senhofer, Justus Liebigs Annalen der Chemie, 1872, vol. 164, p. 118

  摘要：

  DOI：

文献信息

• Oxidation and reduction of some methoxy-anthracenes and their derivatives
  作者：D. W. Cameron、P. E. Schütz

  DOI：10.1039/j39670002121

  日期：——

  rapid and quantitative photo-oxidation to 2,6-dimethoxy-9,10-anthraquinone in normal laboratory daylight. Reduction of this quinone with cyclohexyl toluene-p-sulphonate in the presence of zinc gives a mixture of the corresponding anthracene and 2,2′,6,6′-tetramethoxy-9,9′-bianthryl. Aerial oxidation of 2,6-dimethoxyanthrone in basic media results in formation of the anthraquinone together with the 9,9′-dianthraquinone

  2,6,9-三甲氧基蒽的溶液在正常的实验室日光下快速且定量地光氧化为2,6-二甲氧基-9,10-蒽醌。在锌存在下用环己基甲苯-对磺酸酯还原该醌，得到相应的蒽和2,2'，6,6'-四甲氧基-9,9'-联蒽的混合物。2，6-二甲氧基蒽酮在碱性介质中的空气氧化导致蒽醌与9,9'-二蒽醌（V）以及其他环化醌（VI）和（VII）一起形成。这些反应伴随有新的氧化脱甲基，得到2-羟基-6-甲氧基蒽醌。
• Synthesis of anthraquinone derivatives by palladium-catalyzed coupling of triflates with stannanes.
  作者：Nuria Tamayo、Antonio M. Echavarren、M. Carmen Paredes、Francisco Fariña、Pedro Noheda

  DOI：10.1016/s0040-4039(00)97839-0

  日期：1990.1

  The palladium-catalyzed coupling of hydroxyanthraquinone triflates with stannanes provides an efficient entry into substituted anthraquinones under neutral conditions.

  钯催化的羟基蒽醌三氟甲磺酸酯与锡烷的偶联可在中性条件下有效地取代羟基蒽醌。
• Study of Tetrahydroxylated Anthraquinones—Potential Tool to Assess Degradation of Anthocyanins Rich Food
  作者：Lukáš Kučera、Ondřej Kurka、Martin Golec、Petr Bednář

  DOI：10.3390/molecules26010002

  日期：——

  Degradation of anthocyanins involves scission of the flavonoid skeleton yielding 2,4,6-trihydroxybenzaldehyde (phloroglucinaldehyde, PGA) and a phenolic acid. However, the process is not finished with the formation of PGA, as the consequent condensation of two PGA molecules providing colored hydroxylated anthraquinones was observed for the first time. This process was studied using a combination of preparative column chromatography, nuclear magnetic resonance, liquid chromatography/high resolution tandem mass spectrometry (LC/HRMS2), and quantum calculations using density functional theory. 1,3,5,7-tetrahydroxyanthraquinone (anthrachrysone) and its isomers were found to rise during heating (95 °C) in a buffered PGA model solution (phosphate buffer, pH 7). These compounds were detected in heated red wine after an increase of its pH value. The concentration of the identified anthrachrysone in the red wine reached 0.01 mg·L−1. Presence of those compounds could therefore indicate involvement of certain steps in the processing of plant materials rich in anthocyanins (e.g., utilization of a higher temperature and/or reduction of acidity) or long-term transformation of anthocyanins (potentially, for instance, in archaeological findings such as wine or fruit residues). Additionally, measurement of wine–soil suspensions proved an increase of their pH to the values suitable for anthocyanin cleavage (neutral to slightly alkaline; reached using soil from archaeologically well-known Bull Rock Cave). Although not found in artificially prepared samples (imitations) or authentic materials so far, according to our results the above mentioned conditions are suitable for the formation of tetrahydroxylated anthraquinone derivatives and their monitoring would be beneficial.

  花青素的降解过程包括类黄酮骨架的裂解，产生 2,4,6-三羟基苯甲醛（PGA）和一种酚酸。然而，这一过程并没有随着 PGA 的形成而结束，因为首次观察到两个 PGA 分子随后缩合，产生了彩色羟基蒽醌。研究结合使用了制备柱色谱法、核磁共振、液相色谱/高分辨串联质谱法（LC/HRMS2）以及密度泛函理论的量子计算方法。在缓冲 PGA 模型溶液（磷酸盐缓冲液，pH 值为 7）中发现，1,3,5,7-四羟基蒽醌（蒽醌）及其异构体在加热（95 °C）过程中会升高。加热后的红葡萄酒的 pH 值升高后，也能检测到这些化合物。红葡萄酒中被鉴定出的蒽酮浓度达到了 0.01 mg-L-1。因此，这些化合物的存在可能表明富含花青素的植物材料在加工过程中涉及到某些步骤（例如，利用较高的温度和/或降低酸度）或花青素的长期转化（例如，可能在葡萄酒或水果残渣等考古发现中）。此外，对葡萄酒-土壤悬浮液的测量证明，其 pH 值已升高到适合花青素裂解的值（中性至微碱性；使用考古学上著名的牛石洞土壤）。虽然迄今为止在人工制备的样品（仿制品）或真实材料中还没有发现，但根据我们的研究结果，上述条件适合形成四羟基化的蒽醌衍生物，对其进行监测将是有益的。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。
• Briggs; Nicholls, Journal of the Chemical Society, 1951, p. 1138
  作者：Briggs、Nicholls

  DOI：——

  日期：——