4-hydroxy-nonanal

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-hydroxy-nonanal
• 英文别名: 4-hydroxynonanal；4-hydroxynonenal
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: JKDRLGCUTJVKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻溴苄氧胺盐酸盐 、 4-hydroxy-nonanal 反应 1.0h， 生成 C₁₆H₂₄BrNO₂ 、 C₁₆H₂₄BrNO₂
  参考文献：
  名称：

  简便的肟醚合成：溴化O-苄基羟胺衍生游离羰基化合物

  摘要：

  摘要 脂肪酸的脂质过氧化产生副产物，其中几种羰基化合物在食品毒理学中受到关注。需要检测这些活性醛以进行鉴定和评估。衍生化对于提高它们在液相色谱/高分辨率质谱 (LC/HRMS) 痕量分析中的稳定性和检测能力是必要的。因此，选择溴化 O-苄基羟胺，即 1-((ammoniooxy)methyl)-2-溴苯氯化物作为温和和选择性衍生羰基化合物的新探针。因此在温和的反应和后处理条件下合成了新的肟醚，并具有完整的分析表征。化学反应的相关性用九种醛，特别是共轭和氘标记的醛和两种酮进行评估。实际上，该反应应该适用于大量羰基化合物，用于复杂生物样品中的衍生化，并通过 LC/HRMS 方法选择性检测原位合成的溴化肟醚。图形概要

  DOI：

  10.1080/00397911.2015.1035791
• 作为产物：
  描述：

  亚油酸甲酯 生成 4-hydroxy-nonanal
  参考文献：
  名称：

  Miyashita, Kazuo; Hara, Nobuko; Fujimoto, Kenshiro, Agricultural and Biological Chemistry, 1985, vol. 49, # 9, p. 2633 - 2640

  摘要：

  DOI：

文献信息

• Antioxidative Function and Substrate Specificity of NAD(P)H- dependent Alkenal/one Oxidoreductase
  作者：Ryan A. Dick、Mi-Kyoung Kwak、Thomas R. Sutter、Thomas W. Kensler

  DOI：10.1074/jbc.m105487200

  日期：2001.11

  There are several known routes for the metabolic detoxication of alpha,beta -unsaturated aldehydes and ketones, including conjugation to glutathione and reduction and oxidation of the aldehyde to an alcohol and a carboxylic acid, respectively. In this study, we describe a fourth class of detoxication that involves the reduction of the alpha,beta -carbon = carbon double bond to a single bond. This reaction is catalyzed by NAD(P)H-dependent alkenal/one oxidoreductase (AO), an enzyme heretofore known as leukotriene B-4 12-hydroxydehydrogenase, 15-oxoprostagiandin 13-reductase, and dithiolethione-inducible gene-1. AO is shown to effectively reduce cytotoxic lipid peroxidation products such as 4-hydroxy-2-nonenal (HNE) (k(cat) = 4.0 x 10(3) min(-1); k(cat)/K-m = 3.3 x 10(7) min(-1) M-1) and acrolein (k(cat) = 2.2 x 10(2) min(-1); k(cat)/K-m = 1.5 x 10(6) min(-1) m(-1)) and common industrial compounds such as ethyl vinyl ketone (k(cat) = 9.6 x 10(3) min(-1); k(cat)/K-m = 8.8 x 10(7) min(-1) M-1) and 15-oxoprostaglandin E-1 (k(cat) = 2.4 x 10(3) min(-1); k(cat)/K-m = 2.4 x 10(9) min(-1) M-1). Furthermore, transfection of human embryonic kidney cells with a rat liver AO expression vector protected these cells from challenge with HNE. The concentration of HNE at which 50% of the cells were killed after 24 h increased from similar to 15 mum in control cells to similar to 70 muM in AO-transfected cells. Overexpression of AO also completely abolished protein alkylation by HNE at all concentrations tested (up to 30 muM). Thus, we describe a novel antioxidative activity of a previously characterized bioactive lipid-metabolizing enzyme that could prove to be therapeutically or prophylactically useful due to its high catalytic rate and inducibility.
• A PROCESS FOR THE EXTRACTION OF ANTHOCYANINS FROM BLACK RICE AND COMPOSITION THEREOF
  申请人：Forbes Medi-Tech Inc.

  公开号：EP1490080A1

  公开（公告）日：2004-12-29
• medical use of anthocyanins extracted from black rice
  申请人：Forbes Medi-Tech Inc.

  公开号：EP1490080B1

  公开（公告）日：2010-11-03
• GENES ENCODING CHAVICOL/EUGENOL SYNTHASE FROM THE CREOSOTE BUSH LARREA TRIDENTATA
  申请人：Washington State University

  公开号：EP2046110A2

  公开（公告）日：2009-04-15
• GSH adducts and uses thereof
  申请人：Blair Ian

  公开号：US20080280319A1

  公开（公告）日：2008-11-13

  This invention relates to biomarkers of oxidative stress and their use. Specifically, the invention relates to thiadiazabicyclo-4-oxo-2(E)-nonenal-Glutathione adduct as a novel biomarker of oxidative stress and its diagnostic use.