apo-11-astaxanthinal | 64809-43-4

• 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: apo-11-astaxanthinal
• 英文别名: 5-(2,6,6-trimethyl-3-oxo-4-hydroxy-cyclohex-1-en-1-yl)-3-methyl-penta-2,4-dien-1-al；(2E,4E)-5-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methylpenta-2,4-dienal
• CAS: 64809-43-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: GXLJMSJMXSSYQD-WEYXYWBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  apo-11-astaxanthinal 、 氯乙酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 生成 5-[4(S)-(chloroacetoxy)-3-oxo-2,6,6-trimethyl-cyclohex-1-en-1-yl]-3-methyl-penta-2,4-dien-1-al
  参考文献：
  名称：

  Polyene compounds

  摘要：

  15,15'-二去氢辉黄素及其酯衍生物可用作着色剂和辉黄素的中间体，以及从酮α-异佛酮和其中间体制备辉黄素的方法。

  公开号：

  US04156090A1
• 作为产物：
  描述：

  虾青素 在 air 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 apo-11-astaxanthinal 、 rac-3-Hydroxy-4-oxo-12'-apo-β-carotin-12'-al 、 apo-12'-astaxanthinoic acid 、 apo-8'-astaxanthinol 、 (+/-)-3-Hydroxy-4-oxo-β-jonon
  参考文献：
  名称：

  Analysis of Palmitoyl Apo-astaxanthinals, Apo-astaxanthinones, and their Epoxides by UHPLC-PDA-ESI-MS

  摘要：

  Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl-) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8') conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8?-astaxanthinal). Fragmentation of [M + H](+) and [M + Na](+) parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl the ester bond of the apo-astaxanthin palmitoyl esters was degraded.

  DOI：

  10.1021/jf503520q

文献信息

• US4156090A
  申请人：——

  公开号：US4156090A

  公开（公告）日：1979-05-22
• US7247752B2
  申请人：——

  公开号：US7247752B2

  公开（公告）日：2007-07-24
• Polyene compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US04156090A1

  公开（公告）日：1979-05-22

  15,15'-Didehydro-astaxanthin and ester derivatives thereof useful as coloring agents and intermediates for astaxanthin and a method for preparing astaxanthin from keto .alpha.-isophorone and intermediates therein.

  15,15'-二去氢辉黄素及其酯衍生物可用作着色剂和辉黄素的中间体，以及从酮α-异佛酮和其中间体制备辉黄素的方法。
• Analysis of Palmitoyl Apo-astaxanthinals, Apo-astaxanthinones, and their Epoxides by UHPLC-PDA-ESI-MS
  作者：Yannick Weesepoel、Harry Gruppen、Wouter de Bruijn、Jean-Paul Vincken

  DOI：10.1021/jf503520q

  日期：2014.10.22

  Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl-) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8') conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8?-astaxanthinal). Fragmentation of [M + H](+) and [M + Na](+) parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl the ester bond of the apo-astaxanthin palmitoyl esters was degraded.