(3R,3'R,6'R)-β,ε-carotenyl-3,3'-disuccinate | 264254-32-2

• 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: (3R,3'R,6'R)-β,ε-carotenyl-3,3'-disuccinate
• 英文别名: lutein succinate diester；lutein disuccinate；β,ε-carotenyl 3,3'-disuccinate；β,ε-carotenyl-3,3'-disuccinate；βε-carotenyl-3,3'-disuccinate；4-[(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-(3-carboxypropanoyloxy)-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-yl]oxy-4-oxobutanoic acid
• CAS: 264254-32-2
• 化学式: C₄₈H₆₄O₈
• 分子量: 769.031
• InChiKey: LTPLHBXCAPCQEY-XRYLBMDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  56
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,3'R,6'R)-β,ε-carotenyl-3,3'-disuccinate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以91%的产率得到(3R,3'R,6'R)-β,ε-carotenyl-3,3'-disuccinate disodium salt
  参考文献：
  名称：

  Reduction in complement activation and inflammation during tissue injury by carotenoids, carotenoid analogs, or derivatives thereof

  摘要：

  将水溶性或可分散性的天然类胡萝卜素类似物或衍生物，如虾青素、叶黄素、玉米黄质或番茄红素等，直接给予受试者，可能减少身体器官或组织中炎症的一些不良影响。这些类似物或衍生物可以被加入到药物、非处方药或营养保健制剂中。给予此处描述的类似物或衍生物可能减少炎症介质（如C-反应蛋白、补体系统蛋白或膜攻击复合物（MAC））在组织中的沉积。减少这些分子在组织中的沉积可能减少细胞在组织中的损伤和/或溶解。

  公开号：

  US20060270590A1
• 作为产物：
  描述：

  丁二酸酐 、 叶黄素 在 Candida antarctica lipase B on graphitic carbon nitride nanosheets polyethyleneimine glutaraldehyde 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,3'R,6'R)-β,ε-carotenyl-3,3'-disuccinate
  参考文献：
  名称：

  使用共价固定在功能化石墨氮化碳纳米片上的南极假丝酵母脂肪酶 B 的新型生物催化剂合成叶黄素酯

  摘要：

  叶黄素清除自由基，抑制光氧化造成的视力损伤，同时易受光和热分解。通过叶黄素酯合成可以极大地提高其稳定性和生物利用度。然而，迫切需要绿色高效的酯化制备方法。在这项研究中，使用功能化石墨氮化碳纳米片（gC 3 N 4 -Ns）作为固定载体，设计并制备了一种新型生物催化剂以适应南极念珠菌脂肪酶 B (CALB)，大大提高了性能。通过 TEM、XRD、FTIR、XPS、TGA 和 BET 对其进行表征，证明其制备成功，然后应用于催化叶黄素和琥珀酸酐在二甲基甲酰胺 (DMF) 溶剂中的酯化反应，在 50° 下转化率高达 92% 60 h C，比同等条件下游离CALB高34%。我们相信这是叶黄素酯合成中酯化率最高的，它具有促进环保和高效制备的巨大潜力。

  DOI：

  10.1039/d0ra00563k

文献信息

• [EN] SMALL MOLECULE COMPOUNDS TO SUPPORT HEALTHY HUMAN AGING<br/>[FR] COMPOSÉS À PETITES MOLÉCULES POUR FAVORISER UN VIEILLISSEMENT HUMAIN SAIN
  申请人：CARDAX PHARMA INC

  公开号：WO2018183353A1

  公开（公告）日：2018-10-04

  Disclosed herein are methods of activating expression of the FOXO3 gene in a subject comprising administering to a subject small molecule compound (such as astaxanthin and/or one or more astaxanthin derivatives), or pharmaceutically acceptable salts thereof, in an amount sufficient to at least partially increase the amount of FoxO3 expressed in the subject.

  本文揭示了一种激活主体中FOXO3基因表达的方法，包括向主体施用小分子化合物（如虾青素和/或一个或多个虾青素衍生物）或其药用可接受盐，以足够数量至少部分增加主体中表达的FoxO3的方法。
• Carotenoids, carotenoid analogs, or carotenoid derivatives for the treatment of visual disabilities
  申请人：Lockwood F. Samuel

  公开号：US20060270589A1

  公开（公告）日：2006-11-30

  A method and system used for treating visual disabilities using carotenoids, carotenoid analogs, and/or carotenoid derivatives. The analog, derivative, or intermediate may be administered such that a subject's risk of experiencing diseases associated with visual disabilities may be thereby reduced. Analogs or derivatives of carotenoids may include substituents including for example co-antioxidants (e.g., Vitamin C and Vitamin C analogs). The carotenoid analog or derivative may be synthetic. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

  一种用于治疗视觉障碍的方法和系统，使用类胡萝卜素、类胡萝卜素类似物和/或类胡萝卜素衍生物。类似物、衍生物或中间体可以被施用，以减少受试者患上与视觉障碍相关疾病的风险。类胡萝卜素的类似物或衍生物可能包括取代基，例如共抗氧化剂（例如维生素C和维生素C类似物）。类胡萝卜素的类似物或衍生物可以是合成的。类胡萝卜素的类似物可能包括具有7到14个双键的共轭聚烯。共轭聚烯可能包括至少一个取代基的非环烯烃和/或至少一个取代基的环状环。在某些实施例中，类胡萝卜素的类似物或衍生物可能包括至少一个取代基。取代基可以增强类胡萝卜素的类似物或衍生物的溶解性，使得类胡萝卜素的类似物或衍生物至少部分溶解在水中。
• Hydrophilic Carotenoids: Recent Progress
  作者：Magdolna Háda、Veronika Nagy、József Deli、Attila Agócs

  DOI：10.3390/molecules17055003

  日期：——

  Carotenoids are substantially hydrophobic antioxidants. Hydrophobicity is this context is rather a disadvantage, because their utilization in medicine as antioxidants or in food chemistry as colorants would require some water dispersibility for their effective uptake or use in many other ways. In the past 15 years several attempts were made to synthetize partially hydrophilic carotenoids. This review compiles the recently synthetized hydrophilic carotenoid derivatives.

  类胡萝卜素是一种非常疏水的抗氧化剂。在这种情况下，疏水性是一个缺点，因为将其作为抗氧化剂用于医药或作为着色剂用于食品化学时，需要一定的水分散性才能有效吸收或用于许多其他方面。过去 15 年中，人们曾多次尝试合成部分亲水性类胡萝卜素。本综述汇编了最近合成的亲水性类胡萝卜素衍生物。
• 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。
• 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.