[(2S,3S,4E,6E,8E)-2-acetyloxy-3-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-4,6,8-trienyl] acetate | 166584-44-7

• 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
• 英文名称: [(2S,3S,4E,6E,8E)-2-acetyloxy-3-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-4,6,8-trienyl] acetate
• CAS: 166584-44-7
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: YGCAYDQENMEEKN-CMBAWJKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4E,6E,8E)-2-acetyloxy-3-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-4,6,8-trienyl] acetate 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(2R,3E,5E,7E,9E)-2-acetyloxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-2-en-1-ylidene)nona-3,5,7-trienyl] acetate
  参考文献：
  名称：

  Studies on the Apoptotic Activity of Natural and Synthetic Retinoids:  Discovery of a New Class of Synthetic Terphenyls That Potently Support Cell Growth and Inhibit Apoptosis in Neuronal and HL-60 Cells

  摘要：

  New terphenyl derivatives have been synthesized and tested for their effect on cell survival in serum-free cultures. These compounds protected HL60 cells from death and supported their growth with an activity higher than that of the natural 14-hydroxy-retro-retinol. Terphenyls 26 and 28 also possess antiapoptotic activity on neuronal cells, proving them as possible candidates for the treatment of neurodegenerative and ischemic diseases.

  DOI：

  10.1021/jm049080y
• 作为产物：
  描述：

  维生素 A 醋酸酯 在 potassium osmate(VI) 4-二甲氨基吡啶 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 [(2S,3S,4E,6E,8E)-2-acetyloxy-3-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-4,6,8-trienyl] acetate
  参考文献：
  名称：

  Studies on the Apoptotic Activity of Natural and Synthetic Retinoids:  Discovery of a New Class of Synthetic Terphenyls That Potently Support Cell Growth and Inhibit Apoptosis in Neuronal and HL-60 Cells

  摘要：

  New terphenyl derivatives have been synthesized and tested for their effect on cell survival in serum-free cultures. These compounds protected HL60 cells from death and supported their growth with an activity higher than that of the natural 14-hydroxy-retro-retinol. Terphenyls 26 and 28 also possess antiapoptotic activity on neuronal cells, proving them as possible candidates for the treatment of neurodegenerative and ischemic diseases.

  DOI：

  10.1021/jm049080y

文献信息

• Catalytic enantioselective synthesis of (14R)-14-hydroxy-4,14-retro-retinol from retinyl acetate
  作者：E.J. Corey、Mark C. Noe、Angel Guzman-Perez

  DOI：10.1016/0040-4039(95)00774-7

  日期：1995.6

  A simple and efficient synthesis of the biologically important vitamin A-derived retinoid (14R)-14-hydroxy-4,14-retro-retinol (1) from retinyl acetate in four steps is described.

  描述了从乙酸视黄酯中分四个步骤简单而有效地合成生物学上重要的维生素A衍生的类维生素A（14R）-14-羟基-4,14-复古-视黄醇（1）的方法。
• Studies on the Apoptotic Activity of Natural and Synthetic Retinoids:  Discovery of a New Class of Synthetic Terphenyls That Potently Support Cell Growth and Inhibit Apoptosis in Neuronal and HL-60 Cells
  作者：Daniele Simoni、Giuseppe Giannini、Marinella Roberti、Riccardo Rondanin、Riccardo Baruchello、Marcello Rossi、Giuseppina Grisolia、Francesco Paolo Invidiata、Stefania Aiello、Silvia Marino、Sabrina Cavallini、Anna Siniscalchi、Nicola Gebbia、Lucia Crosta、Stefania Grimaudo、Vincenzo Abbadessa、Antonietta Di Cristina、Manlio Tolomeo

  DOI：10.1021/jm049080y

  日期：2005.6.1

  New terphenyl derivatives have been synthesized and tested for their effect on cell survival in serum-free cultures. These compounds protected HL60 cells from death and supported their growth with an activity higher than that of the natural 14-hydroxy-retro-retinol. Terphenyls 26 and 28 also possess antiapoptotic activity on neuronal cells, proving them as possible candidates for the treatment of neurodegenerative and ischemic diseases.