9-顺式-维甲酸甲基酯 | 58526-50-4

• 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: 9-顺式-维甲酸甲基酯
• 中文别名: 9-顺式视黄酸甲基酯
• 英文名称: [7t,9c,11t,13t]retinoic acid methyl ester
• 英文别名: [7t,9c,11t,13t]Retinsaeure-methylester；9-cis-Retinoic Acid Methyl Ester；methyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate
• CAS: 58526-50-4
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: SREQLAJQLXPNMC-NRWZZFEVSA-N

物化性质

• 溶解度：
  氯仿（微溶）、二氯甲烷（微溶）、己烷（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-顺式-维甲酸甲基酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 9-顺式维甲酸
  参考文献：
  名称：

  Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

  摘要：

  The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<1::aid-jlcr939>3.0.co;2-a
• 作为产物：
  描述：

  2,2,6-三甲基环己酮 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 甲酸 、 乙基溴化镁 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 9-顺式-维甲酸甲基酯
  参考文献：
  名称：

  Synthesis of 9-cis-retinoic acid and C-20-[3H3C]-9-cis-retinoic acid with high specific activity

  摘要：

  The synthesis of 9-cis-retinoic acid starting from 2,2,6-trimethylcyclohexanone is described. The same methodology was extended for the synthesis of deuterium and tritium labeled 9-cis-retinoic acid with high specific activity (73 Ci/mmol). In this methodology, a Grignard reaction was utilized for introducing three tritium atoms simultaneously in the final synthetic steps.

  DOI：

  10.1002/(sici)1099-1344(199701)39:1<1::aid-jlcr939>3.0.co;2-a

文献信息

• Assignment of1H and13C NMR spectra of retinoic acid ester isomers observed in the long-wavelength UV-induced photostationary state
  作者：Robert W. Curley、John W. Fowble

  DOI：10.1002/mrc.1260270722

  日期：1989.7

  13C chemical shift assignments, obtained with the aid of two‐dimensional heteronuclear shift correlation and double‐quantum coherence 13C‐INADEQUATE experiments, are reported for four retinoic acid ester isomers observed at the photo‐stationary state. Also detailed are 1H assignments for three additiona isomers obtained in insufficient amounts for 13C measurements.

  报告了在光静止状态下观察到的四种视黄酸酯异构体的 1H 和 13C 化学位移分配，借助二维异核位移相关和双量子相干 13C-INADEQUATE 实验获得。还详细说明了三种附加异构体的 1H 分配，这些异构体的量不足以进行 13C 测量。
• Means for the modulation of processes mediated by retinoid receptors and compounds useful therefor
  申请人：The Salk Institute for Biological Studies

  公开号：US20040006144A1

  公开（公告）日：2004-01-08

  In accordance with the present invention, there are provided methods to modulate processes mediated by retinoid receptors, employing high affinity, high specificity ligands for such receptors. In one aspect of the present invention, there are provided ligands which are more selective for the retinoid X receptor than is retinoic acid (i.e., rexoids). In another aspect of the present invention, alternative ligands (other than retinoic acid) have been discovered which are capable of inducing retinoic acid receptor mediated processes. In yet another aspect, methods have been developed for the preparation of such retinoid receptor ligands from readily available compounds.

  根据本发明，提供了一种调节由视黄酸受体介导的过程的方法，采用高亲和力、高特异性的配体来调节这些受体。在本发明的一个方面，提供了比视黄酸更具选择性的视黄酸X受体配体（即rexoids）。在另一个方面，发现了除视黄酸以外的其他配体，能够诱导视黄酸受体介导的过程。在另一个方面，还开发了从易得到的化合物中制备这种视黄酸受体配体的方法。
• MEANS FOR THE MODULATION OF PROCESSES MEDIATED BY RETINOID RECEPTORS AND COMPOUNDS USEFUL THEREFOR
  申请人：——

  公开号：US20030105166A1

  公开（公告）日：2003-06-05

  In accordance with the present invention, there are provided methods to modulate processes mediated by retinoid receptors, employing high affinity, high specificity ligands for such receptors. In one aspect of the present invention, there are provided ligands which are more selective for the retinoid X receptor than is retinoic acid (i.e., rexoids). In another aspect of the present invention, alternative ligands (other than retinoic acid) have been discovered which are capable of inducing retinoic acid receptor mediated processes. In yet another aspect, methods have been developed for the preparation of such retinoid receptor ligands from readily available compounds.

  根据本发明，提供了用于调节由视黄醇受体介导的过程的方法，采用对这种受体具有高亲和力和高特异性的配体。在本发明的一个方面，提供了对视黄酸受体X比视黄酸更具选择性的配体（即rexoids）。在本发明的另一方面，发现了除视黄酸以外的其他配体，能够诱导视黄酸受体介导的过程。在另一个方面，开发了从易得化合物制备这种视黄醇受体配体的方法。
• Dimethyl-nonatetraenyl-trimethyl-cyclohexyl compounds and uses thereof
  申请人：The Regents of the University of Michigan

  公开号：US11148998B2

  公开（公告）日：2021-10-19

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a dimethyl-nonatetraenyl-trimethyl-cyclohexyl structure useful as therapeutics for the treatment of subjects suffering from disorders characterized by abnormal proliferation and/or abnormal differentiation of cells, in particular of cells of which the growth and differentiation is sensitive to the actions of retinoids.

  本发明属于药物化学领域。特别是，本发明涉及一类具有二甲基-壬四烯基-三甲基-环己基结构的新的小分子，可作为治疗药物用于治疗以细胞异常增殖和/或异常分化为特征的疾病，特别是生长和分化对维甲酸作用敏感的细胞。
• Chemistry of Vitamin A. XXIV. The Synthesis of Geometric Isomers of Vitamin A via Methyl β-Methylglutaconate¹
  作者：C. D. Robeson、J. D. Cawley、L. Weisler、M. H. Stern、C. C. Eddinger、A. J. Chechak

  DOI：10.1021/ja01620a043

  日期：1955.8