(R)-all-trans-13,14-dihydroretinoic acid | 1007220-99-6

• 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: (R)-all-trans-13,14-dihydroretinoic acid
• 英文别名: all-trans-(R)-13,14-Dihydroretinoic acid；(3R,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-4,6,8-trienoic acid
• CAS: 1007220-99-6
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: XTOYXKSKSDVOOD-BSIQERLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (13R)-13,14-dihydroretinoate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (R)-all-trans-13,14-dihydroretinoic acid
  参考文献：
  名称：

  Stereospecificity of Retinol Saturase:  Absolute Configuration, Synthesis, and Biological Evaluation of Dihydroretinoids

  摘要：

  Retinol saturase carries out a stereospecific saturation of the C13-C14 double bond of all-trans-retinol to generate (13R)-all-trans-13,14-dihydroretinol. This compound is found in cells expressing mouse or zebrafish retinol saturase and in the livers of mice fed retinyl palmitate. All-trans-13,14-dihydroretinol is oxidized in vivo to all-trans-13,14-dihydroretinoic acid, a highly selective agonist of the retinoic acid receptor. The naturally occurring (13R)-all-trans-13,14-dihydroretinoic acid is a weaker agonist than the (13S) enantiomer, indicating enantioselective recognition by the ligand-binding pocket of this receptor. Consequently the (13S) enantiomer, acting through the retinoic acid receptor, also inhibits adipose differentiation more potently than the (13R) enantiomer.

  DOI：

  10.1021/ja710487q

文献信息

• COMPOSITIONS AND METHODS FOR TREATING METABOLIC DISEASES
  申请人：Palczewski Krzysztof

  公开号：US20100135977A1

  公开（公告）日：2010-06-03

  A pharmaceutical composition for treating a metabolic disease in a mammalian subject includes a therapeutically effective amount of all-trans-13,14-dihydroretinoid, all-trans-13,14-dihydroretinoid derivative, or agent capable of modulating the level of at least one all-trans-13,14-dihydroretinoid or all-trans-13,14-dihydroretinoid derivative in the subject.

  一种用于治疗哺乳动物主体代谢性疾病的药物组合物，包括治疗有效量的全反式-13,14-二氢视黄醛、全反式-13,14-二氢视黄醛衍生物或能够调节主体中至少一种全反式-13,14-二氢视黄醛或全反式-13,14-二氢视黄醛衍生物水平的药剂。
• STEREOSELECTIVE SYNTHESIS OF 9-CIS.13,14-DIHYDRORETINOIC ACID AND ITS ETHYL ESTERS
  申请人：UNIVERSITY OF DEBRECEN

  公开号：US20180170867A1

  公开（公告）日：2018-06-21

  The retinoid X receptors (RXRs) are ligand-activated transcription factors heterodimerize with a number of nuclear hormone receptors, thereby controlling a variety of physiological processes. The invention relates to novel enantiomer compounds which are derivatives of dihydroretinoic acid, their stereoselective synthesis, to pharmaceutical compositions containing the same and to the use of same in the treatment of diseases.
• PRECURSOR COMPOUNDS FOR PROVIDING RETINOIDS OF THE VATAMIN A5 PATHWAY AND USES THEREOF
  申请人：UNIVERSITY OF DEBRECEN

  公开号：US20190054056A1

  公开（公告）日：2019-02-21

  The invention relates to the field of retinoid X receptor (RXR) signaling and a novel vitamin A pathway called Vitamin A5 pathway. Compounds which are useful to provide (R)-9-cis-13,14-dihydroretinoic acid, an endogenous RXR ligand, are claimed as well as their uses and method for preparation thereof. The compounds of the invention are useful for pharmaceutical and nutritional uses.
• US8338394B2
  申请人：——

  公开号：US8338394B2

  公开（公告）日：2012-12-25
• US8889660B2
  申请人：——

  公开号：US8889660B2

  公开（公告）日：2014-11-18