4-nitro-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: 4-nitro-β-carotene
• 英文别名: 1,3,3-trimethyl-6-nitro-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohexene
• 化学式: C₄₀H₅₅NO₂
• 分子量: 581.882
• InChiKey: YBVTZGKFSRCARQ-QQGJMDNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  β-胡萝卜素 在 gas-phase research grade 1R₃ cigarette smoke 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 beta-阿朴-14'-胡萝卜醛 、 mutatochrome 、 5,6-epoxy-5,6-dihydro-β,β-carotene 、 4-nitro-β-carotene
  参考文献：
  名称：

  Reactions of β-Carotene with Cigarette Smoke Oxidants. Identification of Carotenoid Oxidation Products and Evaluation of the Prooxidant/Antioxidant Effect

  摘要：

  Recent intervention trials reported that smokers given dietary beta-carotene supplementation exhibited an increased risk of lung cancer and overall mortality. beta-Carotene has been hypothesized to promote lung carcinogenesis by acting as a prooxidant in the smoke-exposed lung. We have examined the interactions of cigarette smoke with beta-carotene in model systems. Both whole smoke and gas-phase smoke oxidized beta-carotene in toluene to several products, including carbonyl-containing polyene chain cleavage products and beta-carotene epoxides. A major product of the reaction was identified as I-nitro-beta-carotene, which was formed by nitrogen oxides in smoke. Both cis and all-trans isomers of 4-nitro-beta-carotene were detected. The hypothesis that smoke-driven p-carotene autoxidation exerts prooxidant effects was tested in a liposome system. Lipid peroxidation in dilinoleoylphosphatidylcholine liposomes exposed to gas-phase smoke was modestly inhibited by the incorporation of 0.1 mol % beta-carotene. Both the lipid soluble antioxidant alpha-tocopherol and the water soluble antioxidant ascorbate were oxidized more slowly by gas-phase smoke exposure in liposomes containing beta-carotene. These data indicate that beta-carotene exerts weak antioxidant effects against smoke-induced oxidative damage in vitro. It is unlikely that a prooxidant effect of beta-carotene occurs under biologically relevent conditions or is responsible for an increased incidence of lung cancer observed in smokers who consume beta-carotene supplements.

  DOI：

  10.1021/tx980263v