all-trans-apo-12'-fucoxanthinal | 22488-61-5

• 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: all-trans-apo-12'-fucoxanthinal
• 英文别名: Apo-12a(2)-fucoxanthinal；(2E,4E,6E,8E,10E)-13-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-2,7,11-trimethyl-12-oxotrideca-2,4,6,8,10-pentaenal
• CAS: 22488-61-5
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: MFXMPUIXRGTKOU-XTGOMCJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  fucoxanthin 在 potassium permanganate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 apo-11'-fucoxanthinal 、 apo-13'-fucoxanthinone 、 apo-15-fucoxanthinal 、 apo-14'-fucoxanthinal 、 all-trans-apo-12'-fucoxanthinal 、 all-trans-apo-12-fucoxanthinal 、 apo-9'-fucoxanthinone 、 (2E,4E,6E)-9-<(1R,2R,4S)-4-acetoxy-2-hydroxy-2,6,6-trimethylcyclohexylidene>-3,7-dimethylnona-2,4,6,8-tetraenal
  参考文献：
  名称：

  Chemical cleavage of fucoxanthin from Undaria pinnatifida and formation of apo-fucoxanthinones and apo-fucoxanthinals identified using LC-DAD-APCI-MS/MS

  摘要：

  As the most abundant carotenoid in nature, fucoxanthin is susceptible to oxidation under some conditions, forming cleavage products that possibly exhibit both positive and negative health effects in vitro and in vivo. Thus, to produce relatively high amounts of cleavage products, chemical oxidation of fucoxanthin was performed. Kinetic models for oxidation were probed and reaction products were identified. The results indicated that both potassium permanganate (KMnO4) and hypochlorous acid/hypochlorite (HClO/ClO-) treatment fitted a first-order kinetic model, while oxidation promoted by hydroxyl radical (OH center dot) followed second-order kinetics. With the help of liquid chromatography-tandem mass spectrometry, a total of 14 apo-fucoxanthins were detected as predominant cleavage products, with structural and geometric isomers identified among them. Three apo-fucoxanthinones and eleven apo-fucoxanthinals, of which five were cis-apo-fucoxanthinals, were detected upon oxidation by the three oxidizing agents (KMnO4, HClO/ClO-, and OH center dot). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2016.05.064