(1E,3E,5E,7E)-9-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl]oxy-3,7-dimethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-1,3,5,7-nonatetraene | 442662-30-8

• 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: (1E,3E,5E,7E)-9-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl]oxy-3,7-dimethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-1,3,5,7-nonatetraene
• 英文别名: diretinyl ether；di-all-trans-retinyl ether；Bis-[3.7-dimethyl-9t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(2t.4t.6t.8)-yl]-aether；Di-[7t.9t.11t.13t]retinyl-aether；Di-all-trans-retinyl-aether；Vitamin A-ether；2-[(1E,3E,5E,7E)-9-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoxy]-3,7-dimethylnona-1,3,5,7-tetraenyl]-1,3,3-trimethylcyclohexene
• CAS: 442662-30-8
• 化学式: C₄₀H₅₈O
• 分子量: 554.9
• InChiKey: ALMBISBNVAOMCL-XBWCUBMNSA-N

物化性质

• 沸点：
  659.0±24.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  维生素A 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(1E,3E,5E,7E)-9-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenyl]oxy-3,7-dimethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-1,3,5,7-nonatetraene
  参考文献：
  名称：

  Efficacy validation of synthesized retinol derivatives In vitro: stability, toxicity, and activity

  摘要：

  Retinol (vitamin A) is used as an antiwrinkle agent in the cosmetics industry. However, its photo-instability makes it unsuitable for use in general cosmetic formulations. To improve the photo-stability of retinol, three derivatives (3, 4, and 5) were synthesized and their biological activities were analyzed. H-1 NMR and HPLC analysis indicated that derivatives 3 and 5 were much more stable than retinol under our sunlight exposure conditions. When human adult fibroblasts were treated, the IC50 of derivative 3 was 96 muM, which is similar to that of retinol, as determined by the MTT assay. Derivatives 4 and 5 were 2.5 and 8 times more toxic than retinol, respectively. At 1 muM treatment, like retinol, derivatives 3 and 4 were specifically active for RARalpha out of six retinoid receptors (RAR/RXRalpha, beta, gamma). Dose-dependent analysis confirmed that derivative 4 was as active as retinol and the other two derivatives were less active for RARalpha. The effect of our derivatives on the expression of collagenase, an indicator of wrinkle formation, was measured using the transient co-expression of c-Jun and RT-PCR in HaCaT cells. Collagenase promoter activity, which is increased by c-Jun expression, was reduced 42% by retinol treatment. The other derivatives inhibited collagenase promoter activity similarly. These results were further confirmed by RT-PCR analysis of the collagenase gene. Taken together, our results suggest that retinol derivative 3 is a promising antiwrinkle agent based on its higher photo-stability, lower RARalpha activity (possibly indicating reduced side effects), and similar effect on collagenase expression. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00334-1

文献信息

• Retinol derivatives, the method of preparations and the uses thereof
  申请人：——

  公开号：US20040023888A1

  公开（公告）日：2004-02-05

  The present invention relates to novel retinol derivatives, the methods of preparation and the uses thereof. According to the present invention, retinol derivatives comprise carboester linkage between di-, tri-, polypeptide having functional group of COOH and retinol. Retinol derivatives in the present invention comprise carboester linkage between amino acid having functional group of di-COOH and retinol. Retinol derivatives comprise carboester linkage between retinol and the compounds having the function group of COOH and multiple double bonds on carbon chain. Retinol derivatives in the present invention comprise carboester linkage between retinol and the compounds having the functional group of di-COOH and one double bond. Retinol derivatives in the present invention comprise ether linkage between the compounds with OH functional group and retinol.

  本发明涉及新型视黄醇衍生物、其制备方法和用途。根据本发明，视黄醇衍生物包括二肽、三肽、多肽具有COOH功能基团和视黄醇之间的碳酸酯键。本发明中的视黄醇衍生物包括具有二级COOH功能基团的氨基酸与视黄醇之间的碳酸酯键。本发明中的视黄醇衍生物包括视黄醇与具有COOH功能基团和碳链上多个双键的化合物之间的碳酸酯键。本发明中的视黄醇衍生物包括视黄醇与具有二级COOH功能基团和一个双键的化合物之间的碳酸酯键。本发明中的视黄醇衍生物包括具有OH功能基团的化合物与视黄醇之间的醚键。
• Retinal derivatives and methods for the use thereof for the treatment of visual disorders
  申请人：University of Washington

  公开号：EP2397130A2

  公开（公告）日：2011-12-21

  Compositions of and methods for using synthetic retinal derivatives as retinoid replacements and opsin agonists are provided.

  本研究提供了合成视黄醛衍生物作为视黄醛替代物和视蛋白激动剂的组成和使用方法。
• Polysaccharide therapeutic conjugates
  申请人：Case Western Reserve University

  公开号：US10226536B2

  公开（公告）日：2019-03-12

  A composition includes a polysaccharide at least one retinoid linked to at least one monosaccharide subunit of the polysaccharide with a covalent linkage. The linkage being degradable by hydrolysis during digestion of the composition to provide controlled, delayed, and/or sustained delivery of the at least one retinoid upon enteral administration of the composition to a subject.

  一种组合物包括一种多糖，其中至少有一种维甲酸与多糖的至少一种单糖亚基以共价键连接。该连接可在组合物消化过程中通过水解降解，从而在对受试者进行肠道给药时提供至少一种维甲酸的可控、延迟和/或持续给药。
• Meunier; Vinet, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1944, vol. 219, p. 141
  作者：Meunier、Vinet

  DOI：——

  日期：——
• Meunier, Bulletin de la Societe Chimique de France, 1946, p. 73,75
  作者：Meunier

  DOI：——

  日期：——