5-香叶氧基-7-甲氧基香豆素 | 7380-39-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 5-香叶氧基-7-甲氧基香豆素
• 中文别名: 5香叶氧基-7-甲氧基香豆素
• 英文名称: 5-geranyloxy-7-methoxycoumarin
• 英文别名: 5-[(2E)-3,7-dimethylocta-2,6-dienoxy]-7-methoxychromen-2-one
• CAS: 7380-39-4
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: WXUOSNJWDJOHGW-XNTDXEJSSA-N

物化性质

• 熔点：
  86-88°C
• LogP：
  5.970 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-香叶氧基-7-甲氧基香豆素 在 甲醇 、 乙醚 、 硫酸 、 溶剂黄146 作用下， 生成 5,7-二甲氧基香豆素
  参考文献：
  名称：

  Chemical Composition of Lemon Oil. I. Isolation of a Series of Substituted Coumarins¹

  摘要：

  DOI：

  10.1021/ja01570a049
• 作为产物：
  描述：

  重氮甲烷 、 5-geranyloxy-7-hydroxycoumarin 以 甲醇 为溶剂， 生成 5-香叶氧基-7-甲氧基香豆素
  参考文献：
  名称：

  Constituents of Clausena excavata. Isolation and Structural Elucidation of Seven New Carbazole Alkaloids and a New Coumarin.

  摘要：

  从新加坡采集的 Clausena excavata（芸香科）茎皮中分离出七种新的咔唑生物碱，命名为 clauszolne-A (1)、-B (2)、-C (3)、-D (4)、-E (5)、-F (6) 和 -G (7)，以及一种新的香豆素，命名为 5-geranyloxy-7-hydroxycomarin (8)，并通过光谱方法阐明了它们的结构。

  DOI：

  10.1248/cpb.44.2231

文献信息

• Color fading/discoloration preventive agent
  申请人：Takasago International Corporation

  公开号：EP1240831A2

  公开（公告）日：2002-09-18

  Disclosed are a color fading/discoloration preventive agent containing as its active ingredient a coumarin analog represented by general formula (1) below, a glycoside of that analog, or a plant extract containing the coumarin analog or its glycoside: (wherein R1 represents a hydrogen atom, a hydroxyl group or a methoxy group, R2 represents a hydrogen atom or a hydroxyl group, and R1 and R2 are not both hydrogen atoms); and a color fading/discoloration preventive agent containing as its active ingredient a coumarin analog mixture obtained from the rind of citrus fruit, and particularly a coumarin analog mixture obtained from citrus cold press oil. The color fading/discoloration preventive agent according to the present invention demonstrates superior color fading/discoloration preventive effects and can be supplied inexpensively by a simple preparation method. In addition, the color fading/discoloration preventive agent provided by the present invention is friendly to the environment and people.

  本发明公开了一种褪色/变色预防剂，其活性成分包括如下通式(1)代表的香豆素类似物、该类似物的苷或含有香豆素类似物或其苷的植物提取物： (其中 R1 代表氢原子、羟基或甲氧基，R2 代表氢原子或羟基，且 R1 和 R2 并非都是氢原子）；以及 一种褪色/变色防止剂，其活性成分是一种从柑橘果皮中提取的香豆素类似物混合物，特别是从柑橘冷榨油中提取的香豆素类似物混合物。本发明的褪色/变色防止剂具有卓越的褪色/变色防止效果，并且可以通过简单的制备方法廉价供应。此外，本发明提供的褪色/变色预防剂对环境和人类都很友好。
• Antibacterial agent
  申请人：Takasago International Corporation

  公开号：EP1240832A2

  公开（公告）日：2002-09-18

  Provided is an antibacterial agent exhibiting an excellent antibacterial activity effect and exerting a mild influence on environment and humanity. The antibacterial agent of the present invention comprises, as an effective component, a mixture of coumarin analogues obtained from a citrus fruit pericarp, particularly a mixture of coumarin analogues obtained from citrus cold press oil.

  本发明提供了一种抗菌剂，具有优异的抗菌活性效果，对环境和人类的影响温和。作为有效成分，本发明的抗菌剂包括从柑橘类果皮中提取的香豆素类似物混合物，特别是从柑橘类冷榨油中提取的香豆素类似物混合物。
• Taste enhancer; process for its production; food, drink, composition for the oral cavity comprising said taste enhancer; method of taste enhancement
  申请人：Takasago International Corporation

  公开号：EP1334665A1

  公开（公告）日：2003-08-13

  A taste enhancer comprising a high-boiling fraction of cold-pressed citrus oil as an active ingredient. The taste enhancer is environment- and human-friendly and, when added to a food, enhances the tastes inherent to the food, such as volume, juiciness, body, and mildness.

  一种由冷榨柑橘油的高沸点馏分作为活性成分组成的增味剂。这种增味剂对环境和人体无害，添加到食品中后，可增强食品固有的口味，如体积、多汁、浓郁和温和。
• Taste enhancer
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20030157240A1

  公开（公告）日：2003-08-21

  A taste enhancer comprising a high-boiling fraction of cold-pressed citrus oil as an active ingredient. The taste enhancer is environment- and human-friendly and, when added to a food, enhances the tastes inherent to the food, such as volume, juiciness, body, and mildness.

  一种由冷榨柑橘油的高沸点馏分作为活性成分组成的增味剂。这种增味剂对环境和人体无害，添加到食品中后，可增强食品固有的口味，如体积、多汁、浓郁和温和。
• Natural oxyprenylated coumarins are modulators of melanogenesis
  作者：Serena Fiorito、Francesco Epifano、Francesca Preziuso、Ivana Cacciatore、Antonio di Stefano、Vito Alessandro Taddeo、Philippe de Medina、Salvatore Genovese

  DOI：10.1016/j.ejmech.2018.04.051

  日期：2018.5

  Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor 13 and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect. The parent compound with a free OH group, umbelliferone, did not provide any interaction. Other coumarins assayed, having shorter chains and/or being substituted in other positions, and prenyloxypsoralens, were not active or not further investigated in this context being cytotoxic at low doses. (C) 2018 Elsevier Masson SAS. All rights reserved.