1,3-二羟基-8-甲氧基-6-甲基蒽-9,10-二酮 | 3775-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,3-二羟基-8-甲氧基-6-甲基蒽-9,10-二酮
• 中文别名: 大黄素-1-甲醚
• 英文名称: 1-O-methylemodin
• 英文别名: 1-methyl emodin；1,3-Dihydroxy-8-methoxy-6-methylanthracene-9,10-dione
• CAS: 3775-08-4
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: IKIAXVIGUJMLHC-UHFFFAOYSA-N

物化性质

• 沸点：
  564.4±50.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)
• 熔点：
  265-268 °C(Solv: methanol (67-56-1))

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

1-O-Methylemodin是一种从Zopfiella longicaudata中分离出的天然产物，具有抗真菌活性。

反应信息

• 作为反应物：
  描述：

  1,3-二羟基-8-甲氧基-6-甲基蒽-9,10-二酮 在 sodium tetrahydroborate 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 3,9,10-trihydroxy-8-methoxy-6-methyl-3,4-dihydroanthracen-1(2H)-one
  参考文献：
  名称：

  A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability

  摘要：

  使用化学酶法合成的天然脱氧蒽醌，经过细胞存活性测试显示与相应的蒽醌相比毒性较低。

  DOI：

  10.1039/d1nj05513e
• 作为产物：
  描述：

  Chan's diene 、 2-chloro-8-methoxy-6-methylnaphthalene-1,4-dione 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 50.0h， 以34%的产率得到1,3-二羟基-8-甲氧基-6-甲基蒽-9,10-二酮
  参考文献：
  名称：

  塔拉木霉（Penicillium islandicum）WF-38-12的蒽酚还原酶的鉴定与表征

  摘要：

  通过基因组分析已经鉴定了来自岛形Talaromyces islandicus WF-38-12的NADPH依赖性氧化还原酶。已显示其催化对映异构和立体选择性的蒽还原反应（对映异构体过量（> 99％））（在Na 2 S 2 O 4存在下通过蒽醌还原原位形成）变为（R）-二氢蒽酮。。讨论了结果对脱氧（双）蒽醌和改性（双）蒽醌的生物合成的影响。

  DOI：

  10.1039/c9gc03072g

文献信息

• Synthesis of (−)-Flavoskyrins by Catalyst-Free Oxidation of (<i>R</i>)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications
  作者：Amit Mondal、Arijit De、Syed Masood Husain

  DOI：10.1021/acs.orglett.0c03121

  日期：2020.11.6

  A catalyst-free method for the synthesis of dimeric (-)-flavoskyrins has been developed. It involves the autoxidation of chemoenzymatically synthesized (R)-configured dihydroanthracenones in the presence of molecular oxygen in buffer of pH 6.0 followed by spontaneous [4 + 2] cycloaddition in stereocontrolled exo-anti fashion to form (-)-flavoskyrins. The method is applied to obtain several homo- as well as heterodimerized flavoskyrins (nine examples) in 27-72% yield and implies the involvement of a similar pathway in the (bio)synthesis of modified bisanthraquinones and their analogues.
• Buchanan, Malcolm S.; Gill, Mclvyn; Millar, Petra, Journal of the Chemical Society. Perkin transactions I, 1999, # 7, p. 795 - 801
  作者：Buchanan, Malcolm S.、Gill, Mclvyn、Millar, Petra、Phonh-Axa, Somphonc、Raudies, Evclin、Yu, Jin

  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.
• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH Zurich

  公开号：EP3801507A2

  公开（公告）日：2021-04-14
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.