(9Z)-lutein | 29414-89-9

• 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: (9Z)-lutein
• 英文别名: 9'-cis-lutein；(9Z,3R,3'R,6'R)-lutein；9-cis-Lutein；(1R)-4-[(1E,3Z,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
• CAS: 29414-89-9
• 化学式: C₄₀H₅₆O₂
• 分子量: 568.883
• InChiKey: KBPHJBAIARWVSC-HPIWMWCCSA-N

物化性质

• 沸点：
  702.3±60.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  叶黄素 在 碘 作用下， 以 正己烷 为溶剂， 反应 0.33h， 生成 (9Z)-lutein 、 (9'Z)-lutein
  参考文献：
  名称：

  黄斑叶黄素分子构型形式的拉曼光谱分析

  摘要：

  黄斑，人眼的视网膜的黄斑，包括三个叶黄素色素：叶黄素，玉米黄质，和中观-zeaxanthin，打了无数重要的生物学功能。由于黄斑位于光轴上，相对于感光体，黄斑叶黄素暴露于眼睛中相对较强的照明。在目前的工作中，我们通过共振拉曼光谱法解决了黄斑叶黄素的光稳定性和可能的​​光异构化问题。结果显示黄斑叶黄素的两个主要异构体全反式和9顺式的光稳定性，以及13顺式异构体向9的有效光转化。顺式，大部分为全反式。我们报告了黄斑叶黄素主要分子构型的拉曼光谱，为检查它们在自然系统中可能存在和进行光转化开辟了一条途径。

  DOI：

  10.1002/jrs.5818

文献信息

• Determination of the geometric configuration of the polyene chain of mono-cis c40 carotenoids II
  作者：M. Baranyai、P. Molnár、J. Szabolcs、L. Radics、M. Kajtár-Peredy

  DOI：10.1016/s0040-4020(01)97736-1

  日期：1981.1

  Systematic chromatography has resulted in the isolation of four geometric isomers as products of iodine-catalysed isomerisation of lutein, 13C NMR spectral analysis has established their stereochemistry as mono-cis luteins with a cis-configured double bond at C-9. C-9', C-13 and C-13', respectively. Carbon-13 NMR has also provided unambiguous stereochemical assignment for the previously isolated four

  系统色谱已分离出作为叶黄素碘催化的异构化产物的四个几何异构体，13 C NMR光谱分析已确定其立体化学为在C-9处具有顺式构型双键的单顺式叶黄素。C-9'，C-13和C-13'。Carbon-13 NMR还为先前分离的四个单顺式辣椒红素提供了明确的立体化学归属。
• Effect of ultrasonic waves on the stability of all-trans lutein and its degradation kinetics
  作者：Jiang-Feng Song、Da-Jing Li、Hui-Li Pang、Chun-Quan Liu

  DOI：10.1016/j.ultsonch.2015.04.020

  日期：2015.11

  Ultrasound treatment has been widely applied in the extraction of biologically active compounds including carotenoids. However, there are few reports on their effects on the stability of these compounds. In the present study, the stability of all-trans lutein, one of the carotenoids, was investigated under the action of ultrasound. Results showed that ultrasound induced the isomerization of all-trans lutein to its isomers, namely to 13-cis lutein, 13'-cis lutein, 9-cis lutein and 9'-cis lutein as analyzed by HPLC coupled with DAD and LC-MS; and the percentage of the isomerization increased with increasing both ultrasonic frequency and power. The stability of all-trans lutein in dichloromethane was worst among multiple kinds of solvents. Interestingly, the retention rate of all-trans lutein improved as the temperature increased, which runs counter to the Arrhenius law. Under ultrasound irradiation, the degradation mechanism might be different with various temperatures, the degradation of all-trans lutein followed first-order kinetics at 20 degrees C, while second-order kinetics was followed at 30-50 degrees C. As the ultrasonic reaction time prolonged, lutein epoxidation nearly occurred. Those results presented here emphasized that UAE techniques should be carefully used in the extraction of all-trans lutein. (C) 2015 Elsevier B.V. All rights reserved.
• Raman spectroscopy analysis of molecular configuration forms of the macular xanthophylls
  作者：A. Sek、R. Welc、M.M. Mendes‐Pinto、E. Reszczynska、W. Grudzinski、R. Luchowski、W.I. Gruszecki

  DOI：10.1002/jrs.5818

  日期：2020.4

  of the macular xanthophylls, all‐trans and 9‐cis, and efficient photoconversion of the 13‐cis isomer to the 9‐cis and mostly to the all‐trans form. We report the Raman spectra of the main molecular configuration forms of the macular xanthophylls, opening an avenue for the examination of their possible presence and photoconversion in natural systems.

  黄斑，人眼的视网膜的黄斑，包括三个叶黄素色素：叶黄素，玉米黄质，和中观-zeaxanthin，打了无数重要的生物学功能。由于黄斑位于光轴上，相对于感光体，黄斑叶黄素暴露于眼睛中相对较强的照明。在目前的工作中，我们通过共振拉曼光谱法解决了黄斑叶黄素的光稳定性和可能的​​光异构化问题。结果显示黄斑叶黄素的两个主要异构体全反式和9顺式的光稳定性，以及13顺式异构体向9的有效光转化。顺式，大部分为全反式。我们报告了黄斑叶黄素主要分子构型的拉曼光谱，为检查它们在自然系统中可能存在和进行光转化开辟了一条途径。