(E)-4,5-epoxy-(E)-2-heptenal | 78307-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-4,5-epoxy-(E)-2-heptenal
• 英文别名: (E)-3-(3-ethyloxiran-2-yl)prop-2-enal
• CAS: 78307-41-2
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: PGTKHYGKDOAHEN-ONEGZZNKSA-N

物化性质

• 沸点：
  223.3±15.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)
• LogP：
  0.525 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-赖氨酸 、 (E)-4,5-epoxy-(E)-2-heptenal 反应 0.01h， 生成 1-(5'-amino-1'-carboxypentyl)pyrrole 、 1-(5'-amino-5'-carboxypentyl)pyrrole 、 1-(5'-amino-5'-carboxypentyl)-2-(1"-hydroxypropyl)pyrrole 、 1-(5'-amino-1'-carboxypentyl)-2-(1"-hydroxypropyl)pyrrole 、 1-(5'-amino-1'-carboxypentyl)-2-<(Z)-1"-propenyl>pyrrole 、 1-(5'-amino-1'-carboxypentyl)-2-<(E)-1"-propenyl>pyrrole
  参考文献：
  名称：

  Characterization of the Products Formed during Microwave Irradiation of the Nonenzymic Browning Lysine/(E)-4,5-Epoxy-(E)-2-heptenal Model System

  摘要：

  Previous studies have shown that a lysine/(E)-4,5-epoxy-(E)-2-heptenal model system may help to elucidate the nonenzymatic browning produced in foods by lipid peroxidation products during microwave heating. As a continuation of those studies, this research was undertaken to isolate and characterize the different compounds that are produced in the above system in order to elucidate the mechanisms that take place at the molecular level upon microwave irradiation. Six pyrrole derivatives were isolated and characterized by H-1 and C-13 nuclear magnetic resonance spectroscopy and mass spectrometry. They were 1-[5'-amino-(1' and 5')-carboxypentyl]pyrrole (3 and 4, respectively), 1-[5'-amino-(1' and 5')-carboxypentyl]-2-(1''-hydroxypropyl)pyrrole (5 and 6, respectively), and 1-(5'-amino-1'-carboxypentyl)-2-[(Z and E)-1''-propenyl]pyrrole (7 and 8, respectively). Two of these compounds (7 and 8) were not previously found during thermic heating at low or moderate temperatures. A possible mechanism that explains the formation of all these compounds is suggested and discussed in relation to the formation of color and fluorescence in this system.

  DOI：

  10.1021/jf00052a033
• 作为产物：
  描述：

  (E,E)-2,4-庚二烯醛 在 间氯过氧苯甲酸 作用下， 生成 (E)-4,5-epoxy-(E)-2-heptenal
  参考文献：
  名称：

  Pyrrolization and Antioxidant Function of Proteins Following Oxidative Stress

  摘要：

  The consequences of oxidative stress on microsomal proteins were analyzed by studying their pyrrolization and the antioxidative activity of the modified proteins produced. The microsomal system consisted of freshly prepared trout muscle microsomes, which were oxidized in the presence of 5 muM Cu2+, 1 mM Fe3+/5 mM ascorbate, or 1 mM Cu2+/10 mM H2O2. Pyrroles on proteins were detected by forming Ehrlich adducts with p-(dimethylamino)benzaldehyde and by determination of epsilon -N-pyrrolylnorleucine (Pnl) by capillary electrophoresis. Their antioxidative activity was studied by testing two model pyrrolized proteins (dimeric and monomeric modified bovine serum albumin: DBSA and MESA, respectively), which were produced in the reaction of BSA and 4,5(E)-epoxy-2(E)-heptenal. These proteins were assayed at a concentration of 10-40 mug/mL, which was selected because at this concentration both DBSA and MESA had a concentration of Pnl similar to the Pnl concentration produced in oxidized microsomes. Both DBSA and MESA significantly (p < 0.05) protected against lipid peroxidation, assessed by the formation of thiobarbituric acid reactive substances (TBARS), and protein damage, evaluated by amino acid analysis, for the three systems assayed, and this protection was always higher than that exhibited by BSA, which was used as control. The order of effectiveness was DBSA > MBSA > BSA and was parallel to the Pnl content in the assayed proteins. These results suggest that antioxidative activity of BSA may also be related to its ability to react with lipid oxidation products and to produce modified BSA with antioxidative activity. This mechanism may also be contributing to the antioxidative activity exhibited by many proteins.

  DOI：

  10.1021/tx000215m

文献信息

• ANTHROPOD REPELLENT CHEMICALS
  申请人：The Regents of the University of California

  公开号：US20160272612A1

  公开（公告）日：2016-09-22

  Compositions and methods for repelling arthropods. The compositions include a carrier and an arthropod repelling compound, which can be a compound discovered by a novel and complex cheminformatic process to demonstrate repellency behavior across a broad spectrum of arthropods. The compound can be a thiane compound, a pyrrolidone compound, a cyclohexadiene compound, a cyclohexenone compound, a cyclohexene compound, a furanone compound, a pyran compound, a tetrahydropyran compound, a thiazolidine compound, a thiazoline compound, a dihydrothiophene compound, a dithiolane compound, a dithiane compound, an epoxide compound, an oxathiane compound, a cyclopentene compound, a cyclohexane compound, a quinoline compound, an oxazoline compound, a tetrahydropyridine compound, and an imidazolidinone compound, or a combination thereof.
• Pyrrolization and Antioxidant Function of Proteins Following Oxidative Stress
  作者：Francisco J. Hidalgo、Manuel Alaiz、Rosario Zamora

  DOI：10.1021/tx000215m

  日期：2001.5.1

  The consequences of oxidative stress on microsomal proteins were analyzed by studying their pyrrolization and the antioxidative activity of the modified proteins produced. The microsomal system consisted of freshly prepared trout muscle microsomes, which were oxidized in the presence of 5 muM Cu2+, 1 mM Fe3+/5 mM ascorbate, or 1 mM Cu2+/10 mM H2O2. Pyrroles on proteins were detected by forming Ehrlich adducts with p-(dimethylamino)benzaldehyde and by determination of epsilon -N-pyrrolylnorleucine (Pnl) by capillary electrophoresis. Their antioxidative activity was studied by testing two model pyrrolized proteins (dimeric and monomeric modified bovine serum albumin: DBSA and MESA, respectively), which were produced in the reaction of BSA and 4,5(E)-epoxy-2(E)-heptenal. These proteins were assayed at a concentration of 10-40 mug/mL, which was selected because at this concentration both DBSA and MESA had a concentration of Pnl similar to the Pnl concentration produced in oxidized microsomes. Both DBSA and MESA significantly (p < 0.05) protected against lipid peroxidation, assessed by the formation of thiobarbituric acid reactive substances (TBARS), and protein damage, evaluated by amino acid analysis, for the three systems assayed, and this protection was always higher than that exhibited by BSA, which was used as control. The order of effectiveness was DBSA > MBSA > BSA and was parallel to the Pnl content in the assayed proteins. These results suggest that antioxidative activity of BSA may also be related to its ability to react with lipid oxidation products and to produce modified BSA with antioxidative activity. This mechanism may also be contributing to the antioxidative activity exhibited by many proteins.
• Characterization of the Products Formed during Microwave Irradiation of the Nonenzymic Browning Lysine/(E)-4,5-Epoxy-(E)-2-heptenal Model System
  作者：Francisco J. Hidalgo、Rosario Zamora

  DOI：10.1021/jf00052a033

  日期：1995.4

  Previous studies have shown that a lysine/(E)-4,5-epoxy-(E)-2-heptenal model system may help to elucidate the nonenzymatic browning produced in foods by lipid peroxidation products during microwave heating. As a continuation of those studies, this research was undertaken to isolate and characterize the different compounds that are produced in the above system in order to elucidate the mechanisms that take place at the molecular level upon microwave irradiation. Six pyrrole derivatives were isolated and characterized by H-1 and C-13 nuclear magnetic resonance spectroscopy and mass spectrometry. They were 1-[5'-amino-(1' and 5')-carboxypentyl]pyrrole (3 and 4, respectively), 1-[5'-amino-(1' and 5')-carboxypentyl]-2-(1''-hydroxypropyl)pyrrole (5 and 6, respectively), and 1-(5'-amino-1'-carboxypentyl)-2-[(Z and E)-1''-propenyl]pyrrole (7 and 8, respectively). Two of these compounds (7 and 8) were not previously found during thermic heating at low or moderate temperatures. A possible mechanism that explains the formation of all these compounds is suggested and discussed in relation to the formation of color and fluorescence in this system.