(3S,3'S)-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester | 264254-35-5

• 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: (3S,3'S)-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester
• 英文别名: disuccinic acid astaxanthin ester；4-[(1S)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-(3-carboxypropanoyloxy)-2,6,6-trimethyl-3-oxocyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-2-oxocyclohex-3-en-1-yl]oxy-4-oxobutanoic acid
• CAS: 264254-35-5
• 化学式: C₄₈H₆₀O₁₀
• 分子量: 796.998
• InChiKey: MUSBCQQQJBPMIT-KQUWWJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3S,3'S)-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester 在 原甲酸三乙酯 、 sodium isopropylate 作用下， 以 异丙醇 为溶剂， 反应 3.5h， 以37%的产率得到(3S,3'S)-sodium succinate mono-(4-{18-[4-(3-carboxypropionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester
  参考文献：
  名称：

  The Efficient Synthesis of Disodium Disuccinate Astaxanthin (Cardax)

  摘要：

  A practical procedure is described for the multigram preparation of disodium disuccinate derivatives of synthetic astaxanthin (Cardax) [from all-trans-(alI-E)-3S,3'S-, meso-(3R,3'S)-, and 3R,3'R-dihydroxy-beta,beta-carotene-4,4'-dione) in a 1:2:1 statistical mixture of stereoisomers, as well as from the individual component stereoisomers]. Process development eliminated chromatographic separations, controlled geometric isomerization, and improved the overall yield of the two-step process, with significant improvements in both the yield and purity of Cardax. Bulk chromatographic separation of the diastereomeric dicamphanic acid ester of synthetic astaxanthin was performed by modifications of the published procedure to subsequently generate multigram quantities of each stereoisomer of disodium disuccinate of astaxanthin.

  DOI：

  10.1021/op049909i
• 作为产物：
  描述：

  丁二酸酐 、 虾青素 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3S,3'S)-succinic acid mono-(4-{18-[4-(3-carboxy-propionyloxy)-2,6,6-trimethyl-3-oxo-cyclohex-1-enyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl}-3,5,5-trimethyl-2-oxo-cyclohex-3-enyl) ester
  参考文献：
  名称：

  10.3390/molecules28186513

  摘要：

  This paper aims to explore the effect and mechanism of water-soluble astaxanthin succinate diester (Asta-SD) on ulcerative colitis (UC) induced by dextran sodium sulfate in zebrafish and C57BL/6J mice. Asta-SD was synthesized with hydrophilic fatty acid succinic anhydride and the hydroxyl groups at the ends of F-Asta were synthesized by esterifying. Through the construction of a zebrafish intestinal inflammation model, it was found that Asta-SD could effectively reduce the levels of ROS and increase the number of healthy intestinal lysosomes in zebrafish. After continuous gavage of Asta-SD for seven days, the body weight, disease activity index, colonic length, colonic histopathology, expression of inflammatory factors, and intestinal flora of the mice were measured. The results showed that Asta-SD could significantly alleviate weight loss and colonic shrinkage, as well as reducing pro-inflammatory cytokines and recess injury in UC mice. The 16S rRNA gene sequencing showed that Asta-SD significantly increased the beneficial bacteria (Lactobacillus, Anaerotruncus) and decreased the relative abundance of pathogenic bacteria, effectively maintaining intestinal microbiota homeostasis in mice. Based on Pearson analysis, Bacteroides, Parabacteroides, and Butyrimionas were expected to be associated with the significant difference in the expression of inflammatory factors between the UC and the corresponding host. Thus, Asta-SD significantly improves UC and maintains intestinal microbiota homeostasis.

  DOI：

  10.3390/molecules28186513

文献信息

• 一种新型抗炎虾青素衍生物的制备方法
  申请人：中国海洋大学

  公开号：CN114213438B

  公开（公告）日：2023-04-14

  本发明涉及一种新型抗炎虾青素衍生物的制备方法，所述新型抗炎虾青素衍生物，以游离虾青素为主体骨架，经琥珀酸酐进行酯化后接枝ROS响应官能团得到所述新型抗炎虾青素衍生物。本发明通过虾青素两端的羟基与琥珀酸酐进行酯化反应，改善虾青素的水分散性，再进一步连接ROS响应官能团，构建具有ROS响应性的虾青素，使其在生物体内有更好的抑制炎症效果。
• The Efficient Synthesis of Disodium Disuccinate Astaxanthin (Cardax)
  作者：Dean A. Frey、Erik W. Kataisto、Juris L. Ekmanis、Sean O'Malley、Samuel F. Lockwood

  DOI：10.1021/op049909i

  日期：2004.9.1

  A practical procedure is described for the multigram preparation of disodium disuccinate derivatives of synthetic astaxanthin (Cardax) [from all-trans-(alI-E)-3S,3'S-, meso-(3R,3'S)-, and 3R,3'R-dihydroxy-beta,beta-carotene-4,4'-dione) in a 1:2:1 statistical mixture of stereoisomers, as well as from the individual component stereoisomers]. Process development eliminated chromatographic separations, controlled geometric isomerization, and improved the overall yield of the two-step process, with significant improvements in both the yield and purity of Cardax. Bulk chromatographic separation of the diastereomeric dicamphanic acid ester of synthetic astaxanthin was performed by modifications of the published procedure to subsequently generate multigram quantities of each stereoisomer of disodium disuccinate of astaxanthin.