11,15'-dihydrooxepino-β,β-carotene-4,4'-dione

• 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: 11,15'-dihydrooxepino-β,β-carotene-4,4'-dione
• 英文别名: 3-[(1E,3E,5E,7E)-3,7-dimethyl-8-[7-methyl-5-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)buta-1,3-dienyl]-4,5-dihydrooxepin-4-yl]octa-1,3,5,7-tetraenyl]-2,4,4-trimethylcyclohex-2-en-1-one
• 化学式: C₄₀H₅₂O₃
• 分子量: 580.851
• InChiKey: SALAITJKDOEZKB-QMPVKDLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  斑蝥黄 在 18-冠醚-6 、 sodium 3-chlorobenzoate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以2%的产率得到11,15'-dihydrooxepino-β,β-carotene-4,4'-dione
  参考文献：
  名称：

  Oxidation of carotenoids — I. Dihydrooxepin derivatives as products of oxidation of canthaxanthin and β,β-carotene

  摘要：

  Dihydrooxepin derivatives 1 and 2 were obtained by oxidation of canthaxanthin with m-CPBA and of beta,beta-carotene with molecular oxygen, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10097-1

文献信息

• Products Formed by Peroxyl Radical-Mediated Oxidation of Canthaxanthin in Benzene and in Methyl Linoleate
  作者：Ryo Yamauchi、Koji Kato

  DOI：10.1021/jf980647r

  日期：1998.12.1

  Canthaxanthin was reacted with peroxyl radicals generated by thermolysis of 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN) in benzene. The reaction products were separated by reversed-phase high-performance liquid chromatography, and their structures were identified as a mixture of 12-formyl-11-nor-beta,beta-carotene-4,4'-dione (1a) and 15'-formyl-15-nor-beta,beta-carotene-4,4'-dione (1b), 15',13-epoxyvinyleno-13, 15'-dihydro-14,15-dinor-beta,beta-carotene-4,4 (2), 13,15'-epoxyvinyleno-13,15'-dihydro-14,15-dinor-beta,beta-carotene-4,4'-dione (3), and 11,15'-dihydrooxepino-beta,beta-carotene-4,4'-dione (4). Compounds 1-4 could be accounted for almost all the consumed canthaxanthin at an early stage of the reaction mixture. The peroxidation of methyl linoleate initiated by AMVN in bulk phase was suppressed by the addition of canthaxanthin. The reaction products of canthaxanthin, 1-4, were also formed during the antioxidant process of canthaxanthin, although their yields were low. The result indicates that the peroxyl radical addition occurred in the antioxidant process of canthaxanthin during the AMVN-initiated peroxidation of methyl linoleate.
• Oxidation of carotenoids — I. Dihydrooxepin derivatives as products of oxidation of canthaxanthin and β,β-carotene
  作者：Marcel Zürcher、Urs A. Niggli、Andrea Steck、Hanspeter Pfander

  DOI：10.1016/s0040-4039(97)10097-1

  日期：1997.11

  Dihydrooxepin derivatives 1 and 2 were obtained by oxidation of canthaxanthin with m-CPBA and of beta,beta-carotene with molecular oxygen, respectively. (C) 1997 Elsevier Science Ltd.