反式-4-羟基-2-己烯醛 | 17427-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 反式-4-羟基-2-己烯醛
• 英文名称: 4-hydroxy-2-hexenal
• 英文别名: 4-hydroxy-hexenal；4-hydroxyhexenal；4-HHE；Hexenal, 4-hydroxy-；4-hydroxyhex-2-enal
• CAS: 17427-08-6
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: JYTUBIHWMKQZRB-UHFFFAOYSA-N

物化性质

• 沸点：
  233.5±23.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)
• LogP：
  0.368 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2912491000

反应信息

• 作为反应物：
  描述：

  反式-4-羟基-2-己烯醛 在 吡啶 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Characterization of Carbonyl–Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal

  摘要：

  4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e., cathechin or quercetin), and the corresponding carbonyl-phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by one- and two-dimensional nuclear magnetic resonance and mass spectrometry as dihydrobenzofuranols (1), chromane-2,7-diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (E-a) of formation were similar to 25 kJ mol(-1) for adducts 1,similar to 32 kJ mol(-1) for adducts 2, and similar to 38 kJ mol(-1) for adducts 3. A reaction pathway that explains their formation is proposed. All of these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl-phenol adducts derived from hydroxyalkenals in food products.

  DOI：

  10.1021/acs.jafc.8b07091
• 作为产物：
  描述：

  3,4-环氧己烷醇 在 periodinane 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 反式-4-羟基-2-己烯醛
  参考文献：
  名称：

  Characterization of Carbonyl–Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal

  摘要：

  4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e., cathechin or quercetin), and the corresponding carbonyl-phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by one- and two-dimensional nuclear magnetic resonance and mass spectrometry as dihydrobenzofuranols (1), chromane-2,7-diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (E-a) of formation were similar to 25 kJ mol(-1) for adducts 1,similar to 32 kJ mol(-1) for adducts 2, and similar to 38 kJ mol(-1) for adducts 3. A reaction pathway that explains their formation is proposed. All of these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl-phenol adducts derived from hydroxyalkenals in food products.

  DOI：

  10.1021/acs.jafc.8b07091

文献信息

• Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D2, and other endogenous and xenobiotic carbonyl compounds
  作者：Satoshi Endo、Toshiyuki Matsunaga、Atsuko Matsumoto、Yuki Arai、Satoshi Ohno、Ossama El-Kabbani、Kazuo Tajima、Yasuo Bunai、Shigeru Yamano、Akira Hara、Yukio Kitade

  DOI：10.1016/j.bcp.2013.08.024

  日期：2013.11

  for NADP(H) over NAD(H) at a physiological pH of 7.4. In the NADPH-linked reduction, 3HBD showed broad substrate specificity for a variety of quinones, ketones and aldehydes, including 3-, 17- and 20-ketosteroids and prostaglandin D(2), which were converted to 3alpha-, 17beta- and 20alpha-hydroxysteroids and 9alpha,11beta-prostaglandin F(2), respectively. Especially, alpha-diketones (such as isatin

  3-羟基己异巴比妥脱氢酶（3HBD）催化将NAD（P）（+）链接的3-羟基己异巴比妥氧化为3-羟基己异巴比妥。该酶被认为是异生物醇和某些羟基类固醇的脱氢酶，但其生理功能仍然未知。我们已经纯化了兔3HBD，分离了其cDNA，并检查了其对辅酶和底物的特异性，反应方向性和组织分布。3HBD是醛酮还原酶（AKR）超家族的成员（AKR1C29），并且在7.4的生理pH值下，NADP（H）优于NAD（H）。在与NADPH相关的还原反应中，3HBD对多种醌，酮和醛（包括3-，17-和20-酮类固醇和前列腺素D（2））显示出广泛的底物特异性，它们被转化为3alpha-，17beta-和20alpha -羟基类固醇和9alpha，11beta-前列腺素F（2），分别。特别是，α-二酮（如isatin和diacetyl）和脂质过氧化衍生的醛（如4-oxo-和4-hydroxy-2-nonenals）是显示低K（m）值（0
• Properties and tissue distribution of a novel aldo–keto reductase encoding in a rat gene (Akr1b10)
  作者：Satoshi Endo、Toshiyuki Matsunaga、Tsukasa Kuragano、Satoshi Ohno、Yukio Kitade、Kazuo Tajima、Ossama El-Kabbani、Akira Hara

  DOI：10.1016/j.abb.2010.08.010

  日期：2010.11

  A recent rat genomic sequencing predicts a gene Akr1b10 that encodes a protein with 83% sequence similarity to human aldo-keto reductase (AKR) 1B10. In this study, we isolated the cDNA for the rat AKR1B10 (R1B10) from rat brain, and examined the enzymatic properties of the recombinant protein. R1B10 utilized NADPH as the preferable coenzyme, and reduced various aldehydes (including cytotoxic 4-hydroxy-2-hexenal and 4-hydroxy- and 4-oxo-2-nonenals) and alpha-dicarbonyl compounds (such as methylglyoxal and 3-deoxyglucosone), showing low K(m) values of 0.8-6.1 mu M and 3.7-67 mu M, respectively. The enzyme also reduced glyceraldehyde and tetroses (K(m) = 96-390 mu M), although hexoses and pentoses were inactive and poor substrates, respectively. Among the substrates, 4-oxo-2-nonenal was most efficiently reduced into 4-oxo-2-nonenol, and its cytotoxicity against bovine endothelial cells was decreased by the overexpression of R1B10. R1B10 showed low sensitivity to aldose reductase inhibitors, and was activated to approximately two folds by valproic acid, and alicyclic and aromatic carboxylic acids. The mRNA for R1B10 was expressed highly in rat brain and heart, and at low levels in other rat tissues and skin fibroblasts. The results suggest that R1B10 functions as a defense system against oxidative stress and glycation in rat tissues. (C) 2010 Elsevier Inc. All rights reserved.
• Characterization of Carbonyl–Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal
  作者：Francisco J. Hidalgo、Rosario Zamora

  DOI：10.1021/acs.jafc.8b07091

  日期：2019.2.20

  4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e., cathechin or quercetin), and the corresponding carbonyl-phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by one- and two-dimensional nuclear magnetic resonance and mass spectrometry as dihydrobenzofuranols (1), chromane-2,7-diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (E-a) of formation were similar to 25 kJ mol(-1) for adducts 1,similar to 32 kJ mol(-1) for adducts 2, and similar to 38 kJ mol(-1) for adducts 3. A reaction pathway that explains their formation is proposed. All of these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl-phenol adducts derived from hydroxyalkenals in food products.