白蜡树精 | 486-28-2

• 物质功能分类: 天然产物 - 香豆素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 白蜡树精
• 英文名称: fraxinol
• 英文别名: 5,7-dimethoxy-6-hydroxycoumarin；6-hydroxy-5,7-dimethoxycoumarin；isofraxidin；umckalin；6-hydroxy-5,7-dimethoxy-chromen-2-one；6-hydroxy-5,7-dimethoxychromen-2-one
• CAS: 486-28-2
• 化学式: C₁₁H₁₀O₅
• 分子量: 222.197
• InChiKey: PBPNOAHYDPHKFH-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172℃
• 沸点：
  449.7±45.0 °C(Predicted)
• 密度：
  1.358
• 溶解度：
  溶于DMSO和甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，Fraxinol 是从半边莲（Lobelia chinensis）中分离出来的。化学性质上，它表现为白色粉末状物质，并可溶于甲醇、乙醇和DMSO等有机溶剂，虽然实际来源应为白蜡树，但表述中可能存在混淆。

用途方面，白蜡树精具有抗真菌、防腐以及活性氨清除的作用。

反应信息

• 作为反应物：
  描述：

  白蜡树精 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以72%的产率得到5,6,7-三甲氧基香豆素
  参考文献：
  名称：

  天然存在的5,6,7-和5,7,8-三加氧香豆素的全合成

  摘要：

  描述了五种天然存在的多加氧香豆素的合成。它涉及两个5,6,7-三加氧香豆素，即6-羟基-5,7-二甲氧基香豆素（fraxinol）1和5,6,7-三甲氧基香豆素2，以及三个5,7,8-三加氧的香豆素，即8-羟基-5,7-二甲氧基（leptodactylone）3，5,7,8- trimethoxycoumarin 4和8-（3-甲基-2-丁烯氧基）-5,7-二甲氧基（artanin）5。合成途径的关键特征是合成合适的四氧化苯甲醛，然后通过维蒂希反应将其转化为相应的香豆素。

  DOI：

  10.1016/j.tet.2008.02.059
• 作为产物：
  描述：

  5,7-二甲氧基香豆素 在 sodium hydroxide 作用下， 生成 白蜡树精
  参考文献：
  名称：

  Bhavsar; Desai, Indian Journal of Pharmacy, 1951, vol. 13, p. 200,203

  摘要：

  DOI：

文献信息

• Toddalenone: A new coumarin from Toddalia asiatica (T. aculeata). Structural establishment based on the chemical conversion of limettin into toddalenone.
  作者：Hisashi Ishii、JunIchi Kobayashi、Tsutomu Ishikawa

  DOI：10.1248/cpb.31.3330

  日期：——

  Toddalenone, a new coumarin, was isolated from Toddalia asiatica (L.) Lam. (T. aculeata Pers.). Its structure was established as the formula (1) by correlation with limettin (2). Vilsmeier-Haack formylation of limettin (2) gave 8-formyllimettin (10) in good yield. Aldol condensation of this material (10) with acetone afforded toddalenone (1).

  从 Toddalia asiatica (L.) Lam.(T. aculeata Pers.）通过与利眠宁（2）的相关性，确定其结构为式（1）。利美丁（2）经 Vilsmeier-Haack 甲酰化后得到 8-formyllimettin（10），收率很高。将这种物质 (10) 与丙酮进行醛醇缩合，可得到托达烯酮 (1)。
• Coumarins from bark of Fraxinus japonica and F. mandshurica var. japonica.
  作者：HIROKI TSUKAMOTO、SUEO HISADA、SANSEI NISHIBE

  DOI：10.1248/cpb.33.4069

  日期：——

  Two biologically active coumarins, scopoletin (1) and isofraxidin (2), along with known coumarins, esculetin (3), fraxetin (4), esculin (5) and fraxin (6), were newly isolated from the bark of Fraxinus japonica BLUME (Oleaceae). On the other hand, the bark of F. mandshurica RUPR. var. japonica MAXIM gave only known coumarins, fraxetin (4), fraxinol (7) and mandshurin (8).

  从水曲柳树皮中新分离出了两种具有生物活性的香豆素：东莨菪素 (1) 和异曲西丁 (2)，以及已知的香豆素：七叶亭 (3)、七叶亭 (4)、七叶亭 (5) 和 fraxin (6)。 （木犀科）。另一方面，F. mandshurica RUPR 的树皮。变种japonica MAXIM 仅提供已知的香豆素、fraxetin (4)、fraxinol (7) 和 mandshurin (8)。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• Furo-chromones and -Coumarins. XII. Synthesis of Fraxinol from Bergapten and of Baicalein from Visnagin
  作者：Alexander Schönberg、Nasry Badran、Nicolas A. Starkowsky

  DOI：10.1021/ja01625a055

  日期：1955.10
• Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
  作者：María E. Riveiro、Dominick Maes、Ramiro Vázquez、Monica Vermeulen、Sven Mangelinckx、Jan Jacobs、Silvia Debenedetti、Carina Shayo、Norbert De Kimpe、Carlos Davio

  DOI：10.1016/j.bmc.2009.08.002

  日期：2009.9

  The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity. (C) 2009 Elsevier Ltd. All rights reserved.