β-carotene cation radical | 57793-67-6

• 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: β-carotene cation radical
• CAS: 57793-67-6
• 化学式: C₄₀H₅₆
• 分子量: 536.885
• InChiKey: CLQZGWONRLSBEC-JLTXGRSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.46
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  海胆烯酮 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 生成 β-carotene cation radical
  参考文献：
  名称：

  电荷离位的类胡萝卜素单和药的亲核反应。

  摘要：

  在本研究中，通过与BF3-醚酸酯进行反应而制得的二芳基（phi，phi-胡萝卜素，异戊二烯）和脂肪族（psi，psi-胡萝卜素，番茄红素）胡萝卜素的阳离子混合物，与β相比，具有更大的复杂性，从而获得了见识。 β-胡萝卜素。由烯丙基类胡萝卜素β，β-胡萝卜素-4-醇（异隐黄质）和β，β-胡萝卜素-4,4'-二醇（异玉米黄质），以及异戊二烯和番茄红素原位制备的单药和除草剂的化学反应是使用选定的O，N和S亲核试剂进行调查; 水，甲醇，叠氮化物和硫代乙酸盐。共分离出22种产品，包括18种新的中性类胡萝卜素产品，并通过VIS，MS和NMR（部分）光谱进行鉴定。它们的结构与阳离子中间体的结构相容。在各种药物中正式添加氢化物，合理化次要反应产物所必需的化合物，将在阳离子反应中更可能发生氢自由基或质子转移的方面进行讨论。对于所有淬灭产物，观察到广泛的E / Z异构化。讨论了类胡萝卜素阳离子在合成4 ,,（

  DOI：

  10.1039/b406913g

文献信息

• Simultaneous electrochemical and electron paramagnetic resonance studies of carotenoid cation radicals and dications
  作者：Mazen Khaled、Andreas Hadjipetrou、Lowell D. Kispert、Robert D. Allendoerfer

  DOI：10.1021/j100159a060

  日期：1991.3

  Comproportionation equilibrium constants have been determined from simultaneous electrochemical and EPR measurements for the carotenoid cation radicals (CAR.+) and dications (CAR2+) of beta-carotene (I), beta-apo-8'-carotenal (II), and canthaxanthin (III). K(I)com = 2.4 x 10(-2), K(com)(II) = 1.8 x 10(-2), K(com)(III) = 2.1 x 10(3). These indicated that, upon oxidation of III, 96% CAR.+ would be formed while 99.7% CAR2+ would be formed for I and II if the oxidation potential was 100 mV anodic of the first observed voltammetric wave. This explains the reason for the strong EPR spectrum observed for III and the weak EPR spectra observed for I and II. Rotating disk experiments confirm that oxidation of carotenoids occurs by an EE rather than by an ECE mechanism and are highly quasireversible systems. The second oxidation peak in the CV spectrum of II has been shown not to be due to a dication analogous to the CV of III but to a radical apparently from the oxidation of a decay product of the dication from II.
• Simultaneous Electrochemical and Electron Paramagnetic Resonance Studies of Carotenoids: Effect of Electron Donating and Accepting Substituents
  作者：A. S. Jeevarajan、M. Khaled、L. D. Kispert

  DOI：10.1021/j100083a006

  日期：1994.8

  A series of substituted phenyl-7'-apocarotenoids with varying electron donating and accepting substituents was examined by cyclic voltammogram (CV) and simultaneous electrochemical electron paramagnetic resonance (SEEPR). Carotenoids substituted with electron donating groups are more easily oxidized than those with electron accepting substituents. Comproportionation constants for the dication and the neutral species were measured by SEEPR techniques and by simulation of the CVs. The Delta H-pp of the SEEPR spectrum of the cation radicals varies from 13.2 to 15.6 G, and the g factors are 2.0027 +/- 0.0002. These EPR parameters suggest a polyene pi-cation radical structure. The CVs are calculated using DigiSim, a CV simulation program, and the proposed mechanism involves three electrode reactions and two homogeneous reactions.