(13alpha,17alpha)-7alpha-乙酰氧基-21,23-环氧-4,4,8-三甲基-24-去甲-5alpha-胆甾-1,14,20,22-四烯-3-酮 | 25279-67-8

• 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: (13alpha,17alpha)-7alpha-乙酰氧基-21,23-环氧-4,4,8-三甲基-24-去甲-5alpha-胆甾-1,14,20,22-四烯-3-酮
• 英文名称: azadirone
• 英文别名: [(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
• CAS: 25279-67-8
• 化学式: C₂₈H₃₆O₄
• 分子量: 436.591
• InChiKey: XXIKKMLIDXLAIK-RFKFVWFBSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  506.5±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (13alpha,17alpha)-7alpha-乙酰氧基-21,23-环氧-4,4,8-三甲基-24-去甲-5alpha-胆甾-1,14,20,22-四烯-3-酮 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Biological investigation and structure–activity relationship studies on azadirone from Azadirachta indica A. Juss

  摘要：

  Azadirone 1, a limonoidal constituent of Azadirachta indica is found to possess potent cytotoxic activity against a panel of human cancer cell lines in our in vitro studies. In vitro screening of a number of semi-synthetic analogues of 1 revealed that the a,p-unsaturated enone moiety or its equivalent conjugated system in A-ring, C-7 acetyloxy/chloroacetyloxy or keto group in B-ring and the furan moiety are responsible for the activity of 1 and its analogues. Compound I and two of the semi-synthetic analogues 10 and 13 were found to possess good in vivo antitumor activity in modified hollow fiber animal models. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.030
• 作为产物：
  描述：

  1,7-di-O-acetyl-14,15-deoxyhavanensin 在 重铬酸吡啶 、 sodium 2,2,2-trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (13alpha,17alpha)-7alpha-乙酰氧基-21,23-环氧-4,4,8-三甲基-24-去甲-5alpha-胆甾-1,14,20,22-四烯-3-酮
  参考文献：
  名称：

  来自 Trichilia havanensis 的柠檬苦素

  摘要：

  摘要 在两个成熟阶段研究了Trichilia havanensis 种子的柠檬苦素类化合物。从未成熟的种子中分离出氮杂二酮、三醋酸哈瓦那菌素和三种新的柠檬苦素。成熟种子含有havanesin三乙酸酯及其羟基内酯衍生物。新的柠檬苦素的结构是通过光谱和化学方法推导出来的。

  DOI：

  10.1016/0031-9422(90)87113-9

文献信息

• Topical composition having undifferentiated plant seed cells and method for using same
  申请人：AVON PRODUCTS, INC.

  公开号：US20030091659A1

  公开（公告）日：2003-05-15

  There is disclosed a topical composition having substantially undifferentiated plant seed cells and, preferably, a pharmaceutically or cosmetically acceptable vehicle. There is also a method for topically applying the composition. There are also methods for delivering a consistent level of an active to skin, nail, lips and/or hair and for enhancing the therapeutic efficacy of a topical composition having substantially undifferentiated plant seed cells.

  本发明揭示了一种含有基本未分化的植物种子细胞的局部组成物，优选地，该组成物还包括药学上或化妆上可接受的载体。还公开了一种局部涂抹该组成物的方法。还公开了将活性物质以一致的水平递送到皮肤、指甲、嘴唇和/或头发的方法，以及增强具有基本未分化的植物种子细胞的局部组成物的治疗功效的方法。
• Complete assignments of the¹H and¹³C NMR spectra of 15 limonoids
  作者：Benjamín Rodríguez

  DOI：10.1002/mrc.1159

  日期：2003.3

  Unambiguous and complete assignments of 1H and 13C NMR chemical shifts for 15 limonoids, eight of them found in natural sources and seven other synthetic derivatives, are presented. The assignments are based on 2D shift‐correlated [1H,1H‐COSY, 1H,13C‐gHSQC‐1J(C,H), 1H,13C‐gHMBC‐nJ(C,H) (n = 2 and 3)] and NOE experiments. Copyright © 2003 John Wiley & Sons, Ltd.

  介绍了 15 种柠檬苦素的 1H 和 13C NMR 化学位移的明确和完整的分配，其中 8 种在天然来源中发现，另外 7 种是其他合成衍生物。分配基于 2D 位移相关 [1H,1H-CO​​SY, 1H,13C-gHSQC-1J(C,H), 1H,13C-gHMBC-nJ(C,H) (n = 2 and 3)] 和NOE 实验。版权所有 © 2003 John Wiley & Sons, Ltd.
• REPELLENT COMPOSITION
  申请人：Athenion AG

  公开号：EP3771335A1

  公开（公告）日：2021-02-03

  The present invention refers to a repellent composition containing margosa oil, lauric acid and a spreading agent. Useful applications of this repellent compositions are also disclosed.

  本发明涉及一种含有马戈萨油、月桂酸和铺展剂的驱虫组合物。本发明还公开了这种驱蚊组合物的有用应用。
• Pest control formulations and methods of making and using same
  申请人：0903608 B.C. Ltd.

  公开号：US10791744B2

  公开（公告）日：2020-10-06

  Compositions useful for controlling pests are disclosed. In some embodiments, the composition includes a pesticidal natural oil and a polar aromatic solvent. Methods of making and using the compositions are disclosed.

  本发明公开了用于控制害虫的组合物。在某些实施方案中，组合物包括杀虫天然油和极性芳香溶剂。还公开了组合物的制造和使用方法。
• Topical cosmetic composition having a natural plant active ingredient and method of using same
  申请人：AVON PRODUCTS, INC.

  公开号：US20030124205A1

  公开（公告）日：2003-07-03

  There are disclosed topical cosmetic compositions having at least one natural active ingredient and a pharmaceutically or cosmetically acceptable vehicle. There is also a method for improving the aesthetic appearance of skin, hair and/or nails that includes topically applying the compositions of the present invention.

  本发明公开了具有至少一种天然活性成分和一种药学上或化妆品上可接受的载体的局部化妆品组合物。还有一种改善皮肤、头发和/或指甲美观的方法，包括局部使用本发明的组合物。