β-cryptoxanthin monosuccinate | 264254-30-0

• 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-cryptoxanthin monosuccinate
• 英文别名: β-cryptoxanthin succinate；4-oxo-4-[(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-3-en-1-yl]oxybutanoic acid
• CAS: 264254-30-0
• 化学式: C₄₄H₆₀O₄
• 分子量: 652.958
• InChiKey: DFZHYGFWTVZMNV-JJVIRXEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-cryptoxanthin monosuccinate 、 隐黄质 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到bis[(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-3-en-1-yl] butanedioate
  参考文献：
  名称：

  Dicarotenoid esters of bivalent acids

  摘要：

  For the evaluation of the synthesis of dendritic esters from carotenoids the C-20 apocarotenoid retinol was chosen for model studies, being a commercially available hydroxy carotenoid. Dimers were synthesized from retinol with dicarboxyl cores and from retinol succinate with other hydroxy carotenoids. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.137
• 作为产物：
  描述：

  丁二酸酐 、 隐黄质 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到β-cryptoxanthin monosuccinate
  参考文献：
  名称：

  Synthesis, Pharmacokinetic Characterization and Antioxidant Capacity of Carotenoid Succinates and Their Melatonin Conjugates

  摘要：

  类胡萝卜素琥珀酸盐由羟基类胡萝卜素合成，并通过酰胺键与市售的褪黑素衍生物偶联，从而生产出更强效的抗氧化剂和具有额外治疗效果的新型混合亲脂双功能分子。偶联反应产生的共轭物收率良好。琥珀酰化增加了类胡萝卜素的水溶性，而与褪黑素共轭则产生了更多亲脂性衍生物。共轭物在水介质中显示出自组装特性，并在磷酸盐缓冲盐水中形成相对稳定的胶体溶液。类胡萝卜素、类胡萝卜素琥珀酸盐以及与褪黑素的共轭物的抗氧化性能是通过 ABTS 和 FRAP 方法测定的。结果表明，抗氧化性与溶剂的质量密切相关。研究发现，新衍生物在磷酸盐缓冲盐水中的 TEAC 值与类胡萝卜素母体的 TEAC 值相当或更高，但只有在 FRAP 分析中观察到了协同作用。

  DOI：

  10.3390/molecules27154822

文献信息

• The first synthesis of PEG–carotenoid conjugates
  作者：Magdolna Háda、Dóra Petrovics、Veronika Nagy、Katalin Böddi、József Deli、Attila Agócs

  DOI：10.1016/j.tetlet.2011.04.039

  日期：2011.6

  Carotenoid-PEG esters and diesters were synthesized from several carotenols with polyethyleneglycols of different chain length to enhance the water solubility and bioavailability of these hydrophobic carotenoids. The water solubility of the products was compared and found, as expected, to be proportional with the PEG content of the conjugates. (C) 2011 Elsevier Ltd. All rights reserved.
• Dicarotenoid esters of bivalent acids
  作者：Magdolna Háda、Veronika Nagy、Anikó Takátsy、József Deli、Attila Agócs

  DOI：10.1016/j.tetlet.2008.03.137

  日期：2008.5

  For the evaluation of the synthesis of dendritic esters from carotenoids the C-20 apocarotenoid retinol was chosen for model studies, being a commercially available hydroxy carotenoid. Dimers were synthesized from retinol with dicarboxyl cores and from retinol succinate with other hydroxy carotenoids. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis, Pharmacokinetic Characterization and Antioxidant Capacity of Carotenoid Succinates and Their Melatonin Conjugates
  作者：Dalma Czett、Katalin Böddi、Veronika Nagy、Anikó Takátsy、József Deli、Paul Tone、György T. Balogh、Anna Vincze、Attila Agócs

  DOI：10.3390/molecules27154822

  日期：——

  Carotenoid succinates were synthesized from hydroxy carotenoids and were coupled to a commercially available derivative of melatonin via amide bond for producing more powerful anti-oxidants and yet new hybrid lipophilic bifunctional molecules with additional therapeutic effects. The coupling reactions produced conjugates in acceptable to good yields. Succinylation increased the water solubility of the carotenoids, while the conjugation with melatonin resulted in more lipophilic derivatives. The conjugates showed self-assembly in aqueous medium and yielded relatively stable colloidal solutions in phosphate-buffered saline. Antioxidant behavior was measured with ABTS and the FRAP methods for the carotenoids, the carotenoid succinates, and the conjugates with melatonin. A strong dependence on the quality of the solvent was observed. TEAC values of the new derivatives in phosphate-buffered saline were found to be comparable to or higher than those of parent carotenoids, however, synergism was observed only in FRAP assays.

  类胡萝卜素琥珀酸盐由羟基类胡萝卜素合成，并通过酰胺键与市售的褪黑素衍生物偶联，从而生产出更强效的抗氧化剂和具有额外治疗效果的新型混合亲脂双功能分子。偶联反应产生的共轭物收率良好。琥珀酰化增加了类胡萝卜素的水溶性，而与褪黑素共轭则产生了更多亲脂性衍生物。共轭物在水介质中显示出自组装特性，并在磷酸盐缓冲盐水中形成相对稳定的胶体溶液。类胡萝卜素、类胡萝卜素琥珀酸盐以及与褪黑素的共轭物的抗氧化性能是通过 ABTS 和 FRAP 方法测定的。结果表明，抗氧化性与溶剂的质量密切相关。研究发现，新衍生物在磷酸盐缓冲盐水中的 TEAC 值与类胡萝卜素母体的 TEAC 值相当或更高，但只有在 FRAP 分析中观察到了协同作用。