5,6-二羟基-7,4'-二甲氧基黄酮 | 10176-71-3

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 5,6-二羟基-7,4'-二甲氧基黄酮
• 英文名称: ladanein
• 英文别名: 5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one；5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)-chromen-4-one；5,6-dihydroxy-7-methoxy-2-(4-methoxyphenyl)chromen-4-one；5,6-dihydroxy-7,4′-dimethoxyflavone；5,6-Dihydroxy-4',7-dimethoxyflavone；5,6-dihydroxy-7,4'-dimethoxyflavone
• CAS: 10176-71-3
• 化学式: C₁₇H₁₄O₆
• 分子量: 314.295
• InChiKey: UUQJTIHOVGMQIH-UHFFFAOYSA-N

物化性质

• 熔点：
  310-313℃
• 沸点：
  565.7±50.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2914509090
• 储存条件：
  2-8℃

制备方法与用途

拉丹素是从百里香中分离出的一种黄酮类化合物。

反应信息

• 作为反应物：
  描述：

  5,6-二羟基-7,4'-二甲氧基黄酮 在 magnesium chloride 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  [EN] FLAVONE DERIVATIVES AND THEIR USE
  [FR] DÉRIVÉS FLAVONIQUES ET LEUR UTILISATION

  摘要：

  本发明涉及黄酮衍生物及含有一种或多种这些黄酮衍生物的组合物。本发明还涉及用于治疗和/或预防病毒感染的黄酮衍生物或组合物，以及预防或治疗这些感染的方法。

  公开号：

  WO2013139487A1
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 dipotassium peroxodisulfate 、 硫酸 、 三溴化硼 、 溶剂黄146 、 sodium hydroxide 、 lithium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 177.0h， 生成 5,6-二羟基-7,4'-二甲氧基黄酮
  参考文献：
  名称：

  Flavone derivatives and their use

  摘要：

  本发明涉及黄酮衍生物及含有一种或多种这些黄酮衍生物的组合物。本发明还涉及用于治疗和/或预防病毒感染的黄酮衍生物或组合物，并涉及一种预防或治疗这些感染的方法。

  公开号：

  EP2641904A1

文献信息

• Iron(<scp>iii</scp>) coordination properties of ladanein, a flavone lead with a broad-spectrum antiviral activity
  作者：X. Martin-Benlloch、A. Novodomska、D. Jacquemin、E. Davioud-Charvet、M. Elhabiri

  DOI：10.1039/c7nj04867j

  日期：——

  The Fe(iii) complexation properties of ladanein, a potent antiviral flavone, and related analogues (negletein and salvigenin), have been studied in solution under quasi-physiological conditions using physico-chemical tools and provided important insights into their stability/reactivity in solution.

  研究了具有强抗病毒作用的黄酮类化合物拉丹内（ladanein）及其相关类似物（negletein和salvigenin）在准生理条件下的Fe（III）络合性质，利用物理化学工具提供了它们在溶液中稳定性/反应性的重要见解。
• Compositions of flavonoids and flavonoid-containing extracts and the treatment of diseases
  申请人：Gong Qiang Bang

  公开号：US20050049206A1

  公开（公告）日：2005-03-03

  In this invention, we describe a group of flavonoids and flavonoid-containing extracts that have pharmaceutical properties which are useful in the medicinal therapy of fibrotic diseases for the treatment or reparation and prevention of fibrotic lesional tissues. Representative flavonoids and flavonoid-containing extracts have the active compositions of the below formula. Those compositions can be extracted and purified from the botanicals, including Scutellaria baicalensis Georgi, Scutellaria scordifolia Fisch,Oroxylum indicum(L.) Vent, Plantago major L. The compositions of the invention are novel as an anti-fibrotic drugs, as agents for treating fibrosis.

  在这项发明中，我们描述了一组黄酮类化合物和含黄酮类化合物的提取物，具有药物特性，可用于治疗纤维化疾病的药物疗法，用于治疗、修复和预防纤维化病变组织。代表性的黄酮类化合物和含黄酮类化合物的提取物具有以下公式的活性成分。这些成分可以从植物中提取和纯化，包括黄芩、紫花地丁、橙黄木、车前草等。本发明的成分作为抗纤维化药物和治疗纤维化的药剂是新颖的。
• Chemical constituents of the leaves of Glochidion obliquum and their bioactivity
  作者：Tran Dinh Thang、Ping-Chung Kuo、Chun-Shu Yu、Yuh-Chiang Shen、Le Thi Mai Hoa、Tran Van Thanh、Yao-Haur Kuo、Mei-Lin Yang、Tian-Shung Wu

  DOI：10.1007/s12272-011-0305-y

  日期：2011.3

  A new flavonoid glycoside, globlin A (1), and eleven known compounds were isolated from methanolic extracts of the leaves of Glochidion obliquum. The structure of this new compound was established with a combination of 2D NMR techniques (COSY, NOESY, HMQC and HMBC) and HR-ESI-MS analyses. Chemical structures of the other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Some of the isolates were examined for their bioactivities. Among the tested compounds, rotundic acid (4) displayed significant cytotoxicity and anti-inflammatory activities.

  从 Glochidion obliquum 叶子的甲醇提取物中分离出了一种新的黄酮苷--globlin A (1)，以及 11 种已知化合物。结合二维核磁共振技术（COSY、NOESY、HMQC 和 HMBC）和 HR-ESI-MS 分析，确定了这种新化合物的结构。通过将其他已知化合物的光谱和物理数据与文献报道的数据进行比较，确定了这些化合物的化学结构。对一些分离物进行了生物活性检测。在测试的化合物中，腐皮酸（4）显示出显著的细胞毒性和抗炎活性。
• Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. XXIII. Demethylation Behaviors of 6-Hydroxy-4',7-dimethoxy-5-tosyloxyflavones with Anhydrous Aluminum Halides in Acetonitrile.
  作者：Tokunaru HORIE、Yoshizumi OHTSURU、Noriko MINAMIMOTO、Kazuyo YAMASHITA、Yasuhiko KAWAMURA、Masao TSUKAYAMA

  DOI：10.1248/cpb.45.1573

  日期：——

  In the demethylation of 6-hydroxy-3, 4', 7-trimethoxy-5-tosyloxyflavone (1) with anhydrous aluminum bromide (AlBr3) or anhydrous aluminum chloride-sodium iodide (AlCl3-NaI) in acetonitrile, the elimination of the 5-tosyloxy group proceeded after demethylation to give 8-bromo-3, 6, 7-trihydroxy-4'-methoxyflavone (6) or 3, 6, 7-trihydroxy-4'-methoxyflavone (5) as a main product. The demethylation of 6-hydroxy-4', 7-dimethoxy-5-tosyloxyflavone (2) with AlCl3-NaI also afforded 6, 7-dihydroxy-4'-methoxyflavone (12), but that with AlBr3 afforded 8-bromo-5, 6, 7-trihydroxy-4'-methoxyflavone (13) as a main product. The demethylation of 1 with anhydrous aluminum chloride (AlCl3) was accompanied by migration of the tosyl group to give a mixture of 3, 6-dihydroxy-7, 4'-dimethoxy-5-tosyloxyflavone (3) and 5-hydroxy-3, 4', 7-trimethoxy-6-tosyloxyflavone (9), but that of 2 proceeded after the cleavage of the 5-tosyloxy group to give a mixture of 5, 6-dihydroxy-7, 4'-dimethoxy- (14) and 5, 6, 7-trihydroxy-4'-methoxyflavones (15) other than the corresponding 6-tosyloxyflavone (16). In the demethylation of the acetates of 1 and 2 with AlCl3, the cleavage of the 5-tosyloxy group proceeded prior to the demethylation to afford the corresponding 5, 6, 7-trihydroxyflavones (8 and 15), although the demethylation of the former acetate was accompanied by formation of 3, 5, 7-trihydroxy-4'-methoxy-6-tosyloxyflavone (10). Mechanisms are proposed for these reactions.

  在乙腈中用无水溴化铝（AlBr3）或无水氯化铝-碘化钠（AlCl3-NaI）对 6-羟基-3，4'，7-三甲氧基-5-甲氧基黄酮（1）进行脱甲基反应时、脱甲基后，5-tosyloxy 基团被消除，主要产物为 8-溴-3，6，7-三羟基-4'-甲氧基黄酮（6）或 3，6，7-三羟基-4'-甲氧基黄酮（5）。用 AlCl3-NaI 对 6-hydroxy-4', 7-dimethoxy-5-tosyloxyflavone (2) 进行脱甲基反应，也可以得到 6, 7-二羟基-4'-甲氧基黄酮 (12)，但用 AlBr3 则可以得到 8-溴-5, 6, 7-三羟基-4'-甲氧基黄酮 (13) 作为主要产物。用无水氯化铝（AlCl3）对 1 进行脱甲基反应时，伴随着甲苯基的迁移，得到 3，6-二羟基-7，4'-二甲氧基-5-甲氧基黄酮（3）和 5-羟基-3，4'，7-三甲氧基-6-甲氧基黄酮（9）的混合物、但 2 在 5-甲氧基基团裂解后，生成了 5，6-二羟基-7，4'-二甲氧基黄酮 (14) 和 5，6，7-三羟基-4'-甲氧基黄酮 (15) 的混合物，而不是相应的 6-甲氧基黄酮 (16)。在用 AlCl3 对 1 和 2 的乙酸酯进行脱甲基反应时，5-tosyloxy 基团先于脱甲基反应发生裂解，从而得到相应的 5、6、7-三羟基黄酮（8 和 15），尽管前一种乙酸酯的脱甲基反应伴随着 3、5、7-三羟基-4'-甲氧基-6-tosyloxy 黄酮（10）的形成。提出了这些反应的机理。
• Chromones and chromone derivatives and uses thereof
  申请人：Yen Mao-Hsiung

  公开号：US20060142211A1

  公开（公告）日：2006-06-29

  The present invention relates to chromones, novel chromone derivatives, and pharmaceutical formulations containing the same and methods of use thereof. Uses of the present invention include, but are not limited to, use for the prevention and treatment of septic shock, organ injury and other disorders. The compounds described herein can be salt forms and also water-soluble compounds.

  本发明涉及香豆素，新型香豆素衍生物，以及含有它们的制药配方和使用方法。本发明的用途包括但不限于预防和治疗败血性休克、器官损伤和其他疾病。所述化合物可以是盐形式和水溶性化合物。