(1S,4R,4aS,8aS)-4-(乙酰氧基)-1,4,4a,5,6,7,8,8a-八氢-1-羟基-5,5,8a-三甲基-1,2-萘二甲醛 | 23599-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S,4R,4aS,8aS)-4-(乙酰氧基)-1,4,4a,5,6,7,8,8a-八氢-1-羟基-5,5,8a-三甲基-1,2-萘二甲醛
• 中文别名: 五酸,γ-内酯(9CI)
• 英文名称: Cinnamodial
• 英文别名: ugandensidial；[(1R,4S,4aS,8aS)-3,4-diformyl-4-hydroxy-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] acetate
• CAS: 23599-45-3
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: UKLMEFSRPRDOLD-YQFWSFKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4R,4aS,8aS)-4-(乙酰氧基)-1,4,4a,5,6,7,8,8a-八氢-1-羟基-5,5,8a-三甲基-1,2-萘二甲醛 在 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 cinnafragrolide
  参考文献：
  名称：

  基于肉桂醛的二聚体（-）-辣椒素的全合成。

  摘要：

  我们描述了基于肉桂醛的二聚体（-）-辣椒素的第一个全合成。首先，我们开发了一种12步合成路线，可从1-乙烯基-2,6,6-三甲基环己烯中获得（-）-肉桂醛。然后，我们证明了（-）-肉桂醛可以在动力学控制的基本条件下选择性地二聚为（-）-辣椒素。我们对（-）-辣椒素的容易转化为（-）-肉桂醛的观察表明，（-）-辣椒素是杀虫性（-）-肉桂醛和肉桂属植物的化学储库，有可能在环境胁迫下释放它。

  DOI：

  10.1021/acs.joc.0c00740
• 作为产物：
  描述：

  [(1R,4S,4aS,8aS)-4-hydroxy-3,4-bis(hydroxymethyl)-4a,8,8-trimethyl-5,6,7,8a-tetrahydro-1H-naphthalen-1-yl] acetate 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 以64%的产率得到(1S,4R,4aS,8aS)-4-(乙酰氧基)-1,4,4a,5,6,7,8,8a-八氢-1-羟基-5,5,8a-三甲基-1,2-萘二甲醛
  参考文献：
  名称：

  基于肉桂醛的二聚体（-）-辣椒素的全合成。

  摘要：

  我们描述了基于肉桂醛的二聚体（-）-辣椒素的第一个全合成。首先，我们开发了一种12步合成路线，可从1-乙烯基-2,6,6-三甲基环己烯中获得（-）-肉桂醛。然后，我们证明了（-）-肉桂醛可以在动力学控制的基本条件下选择性地二聚为（-）-辣椒素。我们对（-）-辣椒素的容易转化为（-）-肉桂醛的观察表明，（-）-辣椒素是杀虫性（-）-肉桂醛和肉桂属植物的化学储库，有可能在环境胁迫下释放它。

  DOI：

  10.1021/acs.joc.0c00740

文献信息

• VERWENDUNG EINES TRP-MODULATORS ZUR PROPHYLAXE UND/ODER LINDERUNG VON WEIDETETANIE UND/ODER GEBÄRPARESE BEI WIEDERKÄUERN ODER SCHWIELENSOHLERN
  申请人：Freie Universität Berlin

  公开号：EP3195857A1

  公开（公告）日：2017-07-26

  Die Erfindung betrifft die neuartige Verwendung eines Futtermittelzusatzes in der Prophylaxe und/oder Linderung von Weidetetanie und/oder Gebärparese in einem Tier aus der Unterordnung der Wiederkäuer (Ruminantia) oder der (wiederkäuenden) Schwielensohler (Tylopoda). Der Futtermittelzusatz enthält mindestens einen TRP-Modulator. Die Erfindung betrifft ferner die neuartige Verwendung eines TRP-Modulators als Arzneimittel in der Behandlung von Weidetetanie und/oder Gebärparese in einem Tier aus der Unterordnung der Wiederkäuer (Ruminantia) oder der (wiederkäuenden) Schwielensohler (Tylopoda).

  本发明涉及一种饲料添加剂在预防和/或缓解反刍动物亚目（Ruminantia）或（反刍动物）胼胝体目（Tylopoda）动物的牧场四肢抽搐症和/或产后瘫痪中的新用途。饲料添加剂中至少含有一种 TRP 调节剂。本发明还涉及一种 TRP 调节剂作为药物治疗反刍动物亚目（Ruminantia）或（反刍动物）胼胝体目（Tylopoda）动物放牧性四肢抽搐和/或产后麻痹的新用途。
• Capsicodendrin from <i>Cinnamosma fragrans</i> Exhibits Antiproliferative and Cytotoxic Activity in Human Leukemia Cells: Modulation by Glutathione
  作者：Soumendrakrishna Karmahapatra、Corey Kientz、Shruthi Shetty、Jack C. Yalowich、L. Harinantenaina Rakotondraibe

  DOI：10.1021/acs.jnatprod.7b00887

  日期：2018.3.23

  Capsicodendrin (CPCD, 1), an epimeric mixture of a dimeric drimane-type sesquiterpene, is one of the major compounds present in the three endemic species of Madagascan traditional chemopreventive plants: Cinnamosma species (C. fragrans, C. macrocarpa, and C. madagascariensis). Despite the popular use of Cinnamosma in Madagascan traditional medicine and the reported antiproliferative properties of CPCD, elucidation of its mechanism(s) of action is still to be accomplished. In the present study, CPCD at low micromolar concentrations was cytotoxic and induced apoptosis in human myeloid leukemia cells in a time- and concentration-dependent manner. The activity of CPCD in HL-60 and K562 cells was modulated by glutathione (GSH), since depletion of this intracellular thiol-based antioxidant with buthionine sulfoximine resulted in significantly (p < 0.05) greater potency in antiproliferation assays. GSH depletion also significantly potentiated the cytotoxic activity in CPCD-treated human HL-60 cells. Single-cell gel electrophoresis (Comet) assays revealed that GSH depletion in HL-60 cells enhanced the formation of DNA strand breaks in the presence of CPCD. Although CPCD does not contain an obvious Michael acceptor in its structure, H-1 NMR analyses indicated that cinnamodial (2), a monomer of CPCD, was formed within a few hours when dissolved in DMSO- d(6) and interacts with GSH to form a covalent bond via Michael addition at the C-7 carbon. Together the results strongly suggest that 2 is responsible for the DNA-damaging, pro-apoptotic, and cytotoxic effects of CPCD and that depletion of GSH enhances overall activity by diminishing covalent interaction between GSH and this 2-alkenal decomposition product of CPCD.
• ZUSAMMENSETZUNGEN ZUR LINDERUNG VON GASTROINTESTINALTRAKTSTÖRUNGEN ODER DAMIT ASSOZIIERTER SYSTEMISCHER STÖRUNGEN VON WIEDERKÄUERN UND CAMELIDEN
  申请人：Freie Universität Berlin

  公开号：EP2879662A1

  公开（公告）日：2015-06-10
• COMPOSITIONS FOR ALLEVIATING GASTROINTESTINAL TRACT DISORDERS OR ASSOCIATED SYSTEMIC DISORDERS IN RUMINANTS AND CAMELIDS
  申请人：FREIE UNIVERSITÄT BERLIN

  公开号：US20150164822A1

  公开（公告）日：2015-06-18

  Provided are feed supplements for the alleviation of gastrointestinal tract disorders and associated systemic disorders in ruminants, methods for producing feed supplements and feeds and feed additives containing such feed supplements. Furthermore, medicaments for the treatment of diseases which are associated with disorders of the gastrointestinal tract, particularly rumen acidosis and parturient paresis, are specified.
• USE OF SESQUITERPENES AND THEIR ANALOGS AS GREEN INSECTICIDES FOR CONTROLLING DISEASE VECTORS AND PLANT PESTS
  申请人：Ohio State Innovation Foundation

  公开号：US20190150437A1

  公开（公告）日：2019-05-23

  Applicant's invention relates to a new class of ‘green’ insecticides for controlling agricultural, medical and veterinary pests. Applicants have identified and optimized natural compounds derived from Madagascan plants that exhibit insecticidal activity on important insect vectors (e.g., mosquitoes) and agricultural pests (e.g., soybean aphids). Plants of the genera Canellaceae, more specifically Cinnamosma , are shown herein to possess sesquiterpene compounds useful for compositions herein. The invention includes novel pesticide compositions, optimized components and methods of use.