迷人醇 | 569-05-1

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 迷人醇
• 英文名称: 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone
• 英文别名: 1,8-Dihydroxy-3-hydroxymethyl-6-methoxyanthrachinon；3-O-methyl-ω-hydroxyemodin；fallacinol；teloschistin；1,8-Dihydroxy-3-hydroxymethyl-6-methoxy-anthrachinon；4.5-Dihydroxy-2-hydroxymethyl-7-methoxy-anthrachinon; Teloschistin；1,8-dihydroxy-3-(hydroxymethyl)-6-methoxyanthracene-9,10-dione
• CAS: 569-05-1
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: WJXSYUJKJSOJOG-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  630.5±55.0 °C(Predicted)
• 密度：
  1.549±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  迷人醇 在 吡啶盐酸盐 作用下， 反应 6.0h， 以76%的产率得到羟基大黄素
  参考文献：
  名称：

  Preparation of functionalized juglone acetates and juglones via 1,4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin

  摘要：

  DOI：

  10.1021/jo00079a042
• 作为产物：
  描述：

  Ethyl 4-(acetyloxy)-6-chloro-5,8-dimethoxy-2-naphthalenecarboxylate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 三氯化铝 、 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 82.0h， 生成 迷人醇
  参考文献：
  名称：

  Preparation of functionalized juglone acetates and juglones via 1,4-dimethoxynaphthalene derivatives: synthesis of anthraquinones related to rhein and aloe-emodin

  摘要：

  DOI：

  10.1021/jo00079a042

文献信息

• In Vitro and in Vivo Studies of the Electrophilicity of Physcion and its Oxidative Metabolites
  作者：Xiaotong Qin、Ying Peng、Jiang Zheng

  DOI：10.1021/acs.chemrestox.8b00026

  日期：2018.5.21

  clinical use. The mechanisms of its toxic action remain unknown. The major objectives of this study were to characterize oxidative metabolites of physcion in vitro and in vivo and to determine the electrophilicity of the parent compound and its oxidative metabolites. Five oxidative metabolites (M1–M5) were detected in rat liver microsomal incubations after exposure to physcion, and the formation of the

  Physcion（1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione）是在何首乌（PMR）中发现的一种生物活性成分，已被广泛用作中药。不幸的是，研究表明PMR在其临床使用期间具有肝毒性。其毒性作用的机制仍然未知。这项研究的主要目的是在体外和体内表征physion的氧化代谢产物，并确定母体化合物及其氧化代谢产物的亲电性。暴露于physion后在大鼠肝微粒体温育中检测到五种氧化代谢物（M1-M5），且代谢物的形成与NADPH依赖。M1-M4是单羟基化代谢物，M5是O-脱甲基化代谢物。一共三个N在以NAC为诱捕剂强化的大鼠肝微粒体中观察到了-乙酰半胱氨酸（NAC）缀合物（M6-M8）。M6衍生自与NAC分子缀合的M4；M7和M8分别来自与NAC分子加成的母体化合物physcion。服用physcion的大鼠尿液中也观察到了M1-M8。HLM
• Studies in anthracycline synthesis: simple Diels-Alder routes to pachybasin, .omega.-hydroxypachybasin, aloe-emodin, and fallacinol
  作者：Nicholas Benfaremo、Michael P. Cava

  DOI：10.1021/jo00201a033

  日期：1985.1
• Asano; Arata, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 521,524; dtsch. Ref. S. 206
  作者：Asano、Arata

  DOI：——

  日期：——
• Characterization of emodin metabolites in Raji cells by LC–APCI-MS/MS
  作者：Junko Koyama、Atsuko Takeuchi、Izumi Morita、Yu Nishino、Maki Shimizu、Munetaka Inoue、Norihiro Kobayashi

  DOI：10.1016/j.bmc.2009.09.024

  日期：2009.11

  A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C(18) AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as omega-hydroxyemodin, 3-O-methyl-omega-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol. (C) 2009 Elsevier Ltd. All rights reserved.
• Anslow; Breen; Raistrick, Biochemical Journal, 1940, vol. 34, p. 159,165
  作者：Anslow、Breen、Raistrick

  DOI：——

  日期：——