(2Z,4E,6Z,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酸 | 5352-74-9

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: (2Z,4E,6Z,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酸
• 中文别名: 9,13-顺,顺视黄酸
• 英文名称: 9,13-di-cis-retinoic acid
• 英文别名: 9,13-dicis-retinoic acid；9-cis-retinoic acid；(9Z,13Z)-retinoic acid；(2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid；[7t,9c,11t,13c]retinoic acid；[7t,9c,11t,13c]Retinsaeure；(2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 5352-74-9
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: SHGAZHPCJJPHSC-CDMOMSTLSA-N

物化性质

• 溶解度：
  氯仿（微溶）、二氯甲烷（微溶）、乙酸乙酯（微溶）
• 物理描述：
  Solid
• 熔点：
  181°C

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z,4E,6Z,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酸 在 碘 作用下， 生成 9-顺式维甲酸
  参考文献：
  名称：

  Chemistry of Vitamin A. XXIV. The Synthesis of Geometric Isomers of Vitamin A via Methyl β-Methylglutaconate¹

  摘要：

  DOI：

  10.1021/ja01620a043
• 作为产物：
  描述：

  9-顺式,13-顺式-视黄醇 在 manganese(IV) oxide 、 silver(II) oxide 作用下， 以 甲醇 为溶剂， 以72%的产率得到(2Z,4E,6Z,8E)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酸
  参考文献：
  名称：

  Stereoselective isomerization of 10-arylsulfenate-11,12-dehydroretinoids to 9-cis-retinoids

  摘要：

  The C-7-C-12 triene fragment of 9-cis-retinoids 8 was stereoselectively generated by treatment of propargylic alcohol 3 with phenylsulfenyl chloride/triethylamine at -78 degrees C, followed by stereospecific reduction of the resulting vinylsulfoxide (t-BuLi, MeLi, MeOH, -78 degrees C). Thus, 9-cis-retinoic acid 2, the natural ligand of the retinoid X receptor (RXR) was straightforwardly synthesized from 8 in two steps. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00810-7

文献信息

• All-Trans-Retinol: All-Trans-13,14-Dihydroretinol Saturase and Methods of Its Use
  申请人：Moise Alexander R.

  公开号：US20080249042A1

  公开（公告）日：2008-10-09

  Compositions of all-trans-retinol: all-trans-13,14-dihydroretinal saturase and methods of use thereof are provided.

  提供了全反式视黄醇的组合物：全反式-13,14-二氢视黄醛饱和酶及其使用方法。
• 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。
• PROCESS FOR PREPARATION OF HIGHLY PURE ISOTRETINOIN
  申请人：Kumar Ashok

  公开号：US20080207946A1

  公开（公告）日：2008-08-28

  The present invention relates to a process for preparation of isotretinoin and more specifically, to a purification process for obtaining highly pure isotretinoin that is useful as a keratolytic agent, particularly useful for the treatment of acne. The process involves treating isotretinoin containing metal contamination and/or other impurities with a base in a suitable solvent to form a solution of isotretinoin, followed by adsorption, precipiation, and filtration or centrifugation

  本发明涉及一种制备异维A酸的过程，更具体地说，涉及一种用于获得高纯度异维A酸的纯化过程，该异维A酸可作为一种角质溶解剂，特别适用于治疗痤疮。该过程涉及用碱处理含有金属污染和/或其他杂质的异维A酸，使其在适当溶剂中形成异维A酸溶液，然后进行吸附、沉淀和过滤或离心的步骤。
• SELECTIVE COMPOUNDS INHIBITING CYP26A1 USEFUL IN COSMETIC AND PHARMACEUTICAL COMPOSITIONS
  申请人：GALDERMA RESEARCH & DEVELOPMENT

  公开号：US20150190323A1

  公开（公告）日：2015-07-09

  Compounds or salts thereof are described that correspond to general formula (I) below: Also described, are pharmaceutical and cosmetic compositions that include these compounds. Methods of using these compounds and compositions for the treatment of pathological conditions are also described.

  本文描述了与下列一般公式（I）相对应的化合物或其盐： 同时还描述了包含这些化合物的药物和化妆品组合物。还描述了使用这些化合物和组合物治疗病理状况的方法。
• Methods and compositions for the treatment of proliferative disorders
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US10265288B2

  公开（公告）日：2019-04-23

  The invention features methods of treating a proliferative disorder characterized by elevated Pin1 marker levels and/or reduced Pin1 Ser71 phosphorylation in a subject by administering a retinoic acid compound. Additionally, the invention features methods of treating proliferative disorders (e.g., proliferative disorders characterized by elevated Pin1 marker levels) by administering a retinoic acid compound in combination with another anti-proliferative compound. Finally, the invention also features methods including high-throughput screens for discovering and validating Pin1 inhibitors.

  本发明的特点是通过施用维甲酸化合物治疗增殖性疾病的方法，该增殖性疾病的特征是受试者体内Pin1标记物水平升高和/或Pin1 Ser71磷酸化降低。此外，本发明还具有通过施用维甲酸化合物与另一种抗增殖化合物联合治疗增殖性疾病（例如，以Pin1标记物水平升高为特征的增殖性疾病）的方法。最后，本发明还包括发现和验证 Pin1 抑制剂的高通量筛选方法。