all-trans-13-demethyl-14-methylretinol | 98754-72-4

• 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
• 英文名称: all-trans-13-demethyl-14-methylretinol
• 英文别名: 2,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraene-1-ol；(2E,4E,6E,8E)-2,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
• CAS: 98754-72-4
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: LCUPCJVMFWHCMV-ORROCPSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  all-trans-13-demethyl-14-methylretinol 在 manganese(IV) oxide 、 sodium carbonate 作用下， 以 乙醚 为溶剂， 反应 2.5h， 以82%的产率得到all-trans-13-demethyl-14-methylretinal
  参考文献：
  名称：

  C11到C14甲基转移的全反式视网膜类似物的合成及其对人醛基酮还原酶的活性。

  摘要：

  人醛基酮还原酶（AKR）是参与将所有反式-视网膜还原为全反式-视黄醇（维生素A）的酶，因此有助于控制生物体中类维生素A的水平。一系列C11-C14甲基转移（相对于天然C13-甲基）全反式的构效关系研究已经报道了-视网膜类似物作为AKR的假定底物。这些类维生素A的合成基于戊烯骨架的C10–C11单键的形成，分别从Stille–Kosugi–Migita和Hiyama–Denmark交叉偶联反应开始，从三苯基碘化物以及相应的二苯基锡烷和二苯基硅烷开始。 。由于这些试剂的不同之处在于二烯基有机金属片段上甲基的位置和存在，因此该研究还提供了对不同位置异构体进行交叉偶联的能力以及这些过程对位阻的敏感性的见解。所得的C11至C14甲基转移的全反式尽管已注意到底物特异性的相关差异，但在用AKR1B1和AKR1B10酶进行测试时，发现视网膜类似物是活性底物。对于AKR1B1，所有类似物均比母体全反式视网膜表现出更高的催化效率（k

  DOI：

  10.1039/d0ob01084g
• 作为产物：
  描述：

  4-(1,4-二甲基-1-乙基)戊基酚 在 sodium tetrahydroborate 、 硫酸 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 19.17h， 生成 all-trans-13-demethyl-14-methylretinol
  参考文献：
  名称：

  类维生素A和相关化合物。第14部分。共轭4-亚烷基丁烯内酯的新颖合成及其光谱表征

  摘要：

  描述了类胡萝卜素亚烷基丁烯内酯的新合成方法（砜法）以及后者的光谱表征。

  DOI：

  10.1039/p19930000987

文献信息

• Derivatives of Alpha-alkyl polyolefinic compounds useful in the treatment of psoriasis
  申请人：USV PHARMACEUTICAL CORPORATION

  公开号：EP0137155A2

  公开（公告）日：1985-04-17

  The present invention relates to novel a-alkyl polyolefinic compounds and to pharmaceuticals containing said compounds. The pharmaceuticals are useful for the treatment of psoriasis. The a-alkyl polyolefinic compounds have the structure wherein n is 0 to 3; R, and R4 are each independently hydrogen or an alkyl group of from 1 to 5 carbon atoms; R2 is an alkyl group of from 1 to 5 carbon atoms; R3 is H, C1-C5 alkyl, cyclo C3-C7 alkyl, C2-C5 alkenyl, cyclo C3-C7 alkenyl, aryl, hydroxy, C1-C5 alkoxy, aryloxy, arylalkoxy, formyl, C1-C6 alkylcarbonyl, C2-C5 alkenylcarbonyl, arylcarbonyl, aryl C1-C5 alkylcarbonyl, aryl C2-C5 alkenylcarbonyl, NR6R5, SR5, retinyloxy, retinoyl, retinoyloxy, or R6 is H, C1-C20 alkyl, aryl, aralkyl; and Z is a cycloalkyl, cycloalkenyl or cycloalkadienyl group substituted with from 0 to 5 alkyl groups, a keto group or a hydroxyl group, or a phenyl group substituted with from 0 to 4 hydroxy, alkoxy, alkyl or trifluoromethyl groups or halogen atoms or combinations thereof; and the pharmaceutically- acceptable salts thereof.

  本发明涉及新型 a-烷基聚烯烃化合物和含有上述化合物的药物。这些药物可用于治疗牛皮癣。a- 烷基聚烯烃化合物具有如下结构 其中 n 为 0 至 3； R 和 R4 各自独立地为氢或 1 至 5 个碳原子的烷基； R2 是 1 至 5 个碳原子的烷基； R3是H、C1-C5烷基、环C3-C7烷基、C2-C5烯基、环C3-C7烯基、芳基、羟基、C1-C5烷氧基、芳氧基、芳烷氧基、甲酰基、C1-C6烷基羰基、C2-C5烯基羰基、芳基羰基、芳基C1-C5烷基羰基、芳基C2-C5烯基羰基、NR6R5、SR5、 视黄氧基、视黄酰基、视黄酰氧基，或 R6 是 H、C1-C20 烷基、芳基、芳烷基；和 Z 是被 0 至 5 个烷基、酮基或羟基取代的环烷基、环烯基或环烷二烯基，或被 0 至 4 个羟基、烷氧基、烷基或三氟甲基或卤原子或其组合取代的苯基；及其药学上可接受的盐。
• Experimental and Theoretical Analysis of the Steric Tolerance of the Binding Site of Bacterioopsin with the Use of Side-Chain Methyl-Shifted Retinal Analogs
  作者：Angel R. de Lera、Beatriz Iglesias、Jesus Rodriguez、Rosana Alvarez、Susana Lopez、Xavier Villanueva、Esteve Padros

  DOI：10.1021/ja00136a021

  日期：1995.8

  Four positional isomers of trans-retinal (1) differing in the location of the side-chain methyl groups have been prepared by a combination of Wittig and highly stereocontrolled Suzuki coupling reactions. The incubation of 9-demethyl-10-methylretinal (5) with bacterioopsin yielded an artificial pigment with an opsin shift of 4630 cm(-1) The other three analogs, namely 13-demethyl-14-methylretinal (3), 13-demethyl-12-methylretinal (4), and 9-demethyl-8-methylretinal (6) did not bind to the apoprotein. In order to rationally address the intrinsic structural differences among analogs which could be relevant to the discrimination exhibited by the protein binding site, ab initio calculations with complete optimization at the 3-21G level were performed on model N-methylretinal iminium salts derived from aldehydes 1 and 3-6. The validity of the approach was inferred from the remarkable coincidence between the minimized structure of N-methylretinal Schiff base (PSB-1) and the structural parameters displayed by N-methyl-N-phenylretinal iminium perchlorate (38b). Computations clearly show that the location of the methyl groups on the polyene side chain is of the utmost importance in determining the overall shape of the retinal ligands. Those structural effects, added to the dominant steric and electronic restrictions of the binding pocket, would explain the observed discrimination among the analogs 3-6, with minor structural changes, and perhaps among other retinals reported in the literature. Additionally, the theoretical and experimental results obtained with 9-demethyl-8-methylretinal (6) provide further indirect evidence of the importance of the 6-s-trans conformation for the native chromophore in bacteriorhodopsin.
• USE OR RETINOIDS TO LOWER PLASMA LEVELS OF LIPOPROTEIN (a)
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0808159A1

  公开（公告）日：1997-11-26
• US4523042A
  申请人：——

  公开号：US4523042A

  公开（公告）日：1985-06-11
• US4614747A
  申请人：——

  公开号：US4614747A

  公开（公告）日：1986-09-30