11,15'-dihydrooxepin-β,β-carotene

• 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'-dihydrooxepin-β,β-carotene
• 英文别名: 5-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-1,3,5,7-tetraenyl]-2-methyl-4-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)buta-1,3-dienyl]-4,5-dihydrooxepine
• 化学式: C₄₀H₅₆O
• 分子量: 552.884
• InChiKey: HNVSNCCUONZQCU-HJBKJGAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  β-胡萝卜素 在 氧气 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 11,15'-dihydrooxepin-β,β-carotene
  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

• Subsequent Products After Antioxidant Actions of β-Carotene and α-Tocopherol Have No<i>Salmonella</i>Mutagenicity
  作者：Mingzhou SUN、Ryo YAMAUCHI、Hitoshi ASHIDA、Kazuki KANAZAWA

  DOI：10.1271/bbb.66.363

  日期：2002.1

  β-Carotene and α-tocopherol are important antioxidants biologically, but whether their oxidized products are toxic or not remains to be discovered. Here, we chromatographically separated 5 pure products or isomeric mixtures from reaction mixtures of β-carotene and reactive oxygens, and 17 lipid-radical scavenging products of α-tocopherol. The products were tested for mutagenicity using Salmonella typhimurium TA98, TA100, TA102, and TA104, in the presence and absence of S9. None showed mutagenicity against any of the four strains, or cytotoxicity that influenced the survival of the bacteria. Lipid-peroxides have been known to increase the formation of mutagens from dietary procarcinogens such as heterocyclic amines. So, we also measured the activity to increase 3-amino-1-methyl- 5H-pyrido[4,3-b]indole (Trp-P-2) mutagenicity. The products from β-carotene and α-tocopherol did not increase, but rather several of them suppressed, the mutagenicity of Trp-P-2. Thus, the products of β-carotene and α-tocopherol formed after the antioxidant actions were not genotoxic.

  β-胡萝卜素和α-生育酚是重要的生物抗氧化剂，但其氧化产物是否具有毒性仍有待发现。在这里，我们从β-胡萝卜素和活性氧的反应混合物中分离出了5种纯产物或异构混合物，并从α-生育酚的反应混合物中分离出了17种清除脂质自由基的产物。在 S9 存在和不存在的情况下，使用鼠伤寒沙门氏菌 TA98、TA100、TA102 和 TA104 对这些产品进行了诱变性测试。结果表明，这四种产品对任何一种菌株都没有诱变作用，也没有影响细菌存活的细胞毒性。众所周知，脂质过氧化物会增加杂环胺等膳食致癌物质诱变剂的形成。因此，我们还测量了增加 3-氨基-1-甲基-5H-吡啶并[4,3-b]吲哚（Trp-P-2）致突变性的活性。β-胡萝卜素和α-生育酚的产物并没有增加，相反，其中几种产物抑制了 Trp-P-2 的致突变性。因此，β-胡萝卜素和α-生育酚在抗氧化作用后形成的产物不具有遗传毒性。
• Oxidation Products of β-Carotene during the Peroxidation of Methyl Linoleate in the Bulk Phase
  作者：Ryo YAMAUCHI、Kakue TSUCHIHASHI、Koji KATO

  DOI：10.1271/bbb.62.1301

  日期：1998.1

  Methyl linoleate containing β-carotene was autoxidized or photooxidized at 37°C in the bulk phase, and the oxidation products of β-carotene were analyzed by high-performance liquid chromatography. Formyl β-carotenes, β-carotene 5,6-epoxide, and cyclic ethers of β-carotene were detected as the oxidation products during the peroxidation of methyl linoleate initiated by a free radical initiator. These

  在本体相中于37℃将含有β-胡萝卜素的亚油酸甲酯自氧化或光氧化，并通过高效液相色谱法分析β-胡萝卜素的氧化产物。在自由基引发剂引发的亚油酸甲酯过氧化过程中，甲酰β-胡萝卜素，β-胡萝卜素5，6-环氧化物和β-胡萝卜素的环状醚被检测为氧化产物。在没有引发剂的情况下，在自氧化的亚油酸甲酯中也检测到了这些产物，仅能以比消耗的β-胡萝卜素小得多的量检测到这些产物。在叶绿素敏化的光氧化过程中，产物为β-胡萝卜素5,8-内过氧化物和β-胡萝卜素5,6-环氧化物。α-生育酚部分抑制了5,6-环氧化物的形成，但对主要产物5,8-内过氧化物没有影响。
• 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.