trans-4-hydroxy-2-hexenal | 17427-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-4-hydroxy-2-hexenal
• 英文别名: (2E)-4-hydroxyhex-2-enal；(E)-4-hydroxy-2-hexenal；(E)-4-hydroxyhex-2-enal；4-hydroxy-2(E)-hexenal；4-hydroxy-2E-hexenal；4-hydroxy-2-hexenal；4-Hydroxyhexenal
• CAS: 17427-21-3
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: JYTUBIHWMKQZRB-ONEGZZNKSA-N

物化性质

• 沸点：
  89-90 °C(Press: 2 Torr)
• 密度：
  0.980±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：50mg/mL； DMSO：50mg/mL；乙醇：>50mg/mL； PBS pH 7.2：>1 mg/mL

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

ADMET

代谢

尿素毒素往往会因为饮食过量或者肾脏过滤功能不佳而在血液中积聚。大多数尿素毒素是代谢废物，通常通过尿液或粪便排出。

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

尿毒症毒素，如4-羟基己烯醛，通过有机离子转运体（特别是OAT3）积极运输到肾脏中。尿毒症毒素水平的增加可以刺激活性氧种类的产生。这似乎是通过尿毒症毒素直接结合或抑制NADPH氧化酶（特别是肾脏和心脏中丰富的NOX4）来介导的（A7868）。活性氧种类可以诱导几种不同的DNA甲基转移酶（DNMTs），这些酶涉及到一种名为KLOTHO的蛋白的沉默。KLOTHO已被识别出在抗衰老、矿物质代谢和维生素D代谢中具有重要作用。许多研究指出，在急性或慢性肾脏疾病中，由于局部活性氧种类水平升高，KLOTHO mRNA和蛋白水平会降低（A7869）。

Uremic toxins such as 4-Hydroxyhexenall are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

长期暴露于尿毒症毒素可能会导致多种疾病，包括肾脏损伤、慢性肾病和心血管疾病。

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

内源性的，摄入，皮肤（接触）

Endogenous, Ingestion, Dermal (contact)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

作为尿毒症毒素，这种化合物可以引起尿毒症综合征。尿毒症综合征可能影响身体的任何部位，并可能导致恶心、呕吐、食欲丧失和体重减轻。它还可能引起精神状态的变化，如混乱、意识减退、躁动、精神疾病、癫痫和昏迷。还可能出现异常出血，例如因非常轻微的损伤而自发或大量出血。心脏问题，如心律不齐、心脏包膜（心包炎）炎症和心脏压力增加，也可能出现在尿毒症综合征患者身上。由于肺部和胸壁之间（胸腔积液）的液体积聚导致的呼吸急促也可能出现。

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  trans-4-hydroxy-2-hexenal 以43%的产率得到(2E)-4-hydroxyoct-2-enal
  参考文献：
  名称：

  (2E)-4-hydroxyalk-2-enals and 2-substituted furans as products of reactions of (2E)-4,4-dimethoxybut-2-enal with Grignard compounds

  摘要：

  Methods have been developed for the synthesis of (2E)-1,1-dimethoxyalk-2-en-4-ols and (2E)-4-hydroxyalk-2-enals by reaction of (2E)-4,4-dimethoxybut-2-enals and Grignard compounds. Thermal isomerization of (2E)-4-hydroxyalk-2-enals gave the corresponding 2-alkylfurans.

  DOI：

  10.1134/s1070428010030188
• 作为产物：
  描述：

  反式-2-己烯醛二甲基乙缩醛 生成 trans-4-hydroxy-2-hexenal
  参考文献：
  名称：

  �ber die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 2. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, I

  摘要：

  DOI：

  10.1007/bf01167149

文献信息

• ALDEHYDE CONJUGATES AND USES THEREOF
  申请人：Aldeyra Therapeutics, Inc.

  公开号：US20200246345A1

  公开（公告）日：2020-08-06

  The present invention provides compounds and methods of use thereof for the treatment, prevention, and/or reduction of a risk of a disease, disorder, or condition in which aldehyde toxicity is implicated in the pathogenesis, including ocular disorders, skin disorders, conditions associated with injurious effects from blister agents, and autoimmune, inflammatory, neurological and cardiovascular diseases by the use of a primary amine to scavenge toxic aldehydes, such as MDA and HNE.

  本发明提供了化合物及其使用方法，用于治疗、预防和/或减少由醛毒性引起病理发生的疾病、紊乱或状况的风险，包括眼部疾病、皮肤疾病、与水泡剂引起的有害效应相关的状况，以及自身免疫、炎症、神经和心血管疾病，通过使用一种主要胺来清除有毒醛类化合物，如MDA和HNE。
• Tandem IBX‐Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ‐Diolcarbonate Aldehydes to ( <i>E</i> )‐γ‐Hydroxy‐α,β‐enals
  作者：Anupama Kumari、Sachin P. Gholap、Rodney A. Fernandes

  DOI：10.1002/asia.201900421

  日期：2019.7

  A tandem IBX‐promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ‐diolcarbonate aldehyde to (E)‐γ‐hydroxy‐α,β‐enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)‐olefin and no over‐oxidation of γ‐hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)‐ and (R)‐coriolides and

  已经开发出串联IBX促进伯醇氧化为醛，并将中间的β，γ-二醇碳酸酯醛打开为（E）-γ-羟基-α，β-烯醛。值得注意的是，碳酸盐开口仅释放了（E）-烯烃，没有观察到γ-羟基的过度氧化。开发的方法已经延伸到完成两个（的立体选择性全合成小号） -和（- [R）-coriolides和d -木糖-和d -阿拉伯-C-20 guggultetrols。
• Specific markers of lipid peroxidation
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1411041A1

  公开（公告）日：2004-04-21

  The present invention concerns a 4-hydroxy-2E-alkenoic acid according to formula (I) below    in which R is chosen in the group consisting of CH3-, CH3-(CH2)3- and CH3-(CH2)3-CH=CH- and its use as lipid peroxidation marker. The present invention also concerns methods to determine its presence and its level in solution and methods for the diagnosis of a pathology involving an increase in lipid peroxidation and for following the effectiveness of the treatment of said pathologies.

  本发明涉及一种根据下式（I）的4-羟基-2E-烯酸 其中R选自CH3-、CH3-(CH2)3-和CH3-(CH2)3-CH=CH-的群组，并且其用作脂质过氧化标记物。本发明还涉及确定其在溶液中的存在和水平的方法，以及用于诊断涉及脂质过氧化增加的病理的方法，以及用于跟踪治疗所述病理的有效性的方法。
• An expeditious synthesis of 4-hydroxy-2(E)-nonenal (4-HNE), its dimethyl acetal and of related compounds
  作者：Laurent Soulère、Yves Queneau、Alain Doutheau

  DOI：10.1016/j.chemphyslip.2007.07.003

  日期：2007.12

  The facile one step synthesis of 4-hydroxy-2E-nonenal and its dimethyl acetal via a cross-metathesis reaction between commercially available octen-3-ol and acrolein or its dimethyl acetal is reported. The method was extended to the synthesis of C6 and C12 4-hydroxy-2E-enals, their dimethyl acetal and of the 4-hydroxy-2E-nonenoic acid (4-HNA).

  据报道，通过可商购的辛烯-3-醇和丙烯醛或其二甲基乙缩醛之间的交叉复分解反应，可以容易地一步合成4-羟基-2E-壬烯醛及其二甲基乙缩醛。该方法扩展到合成C6和C12 4-羟基-2E-烯醛，它们的二甲基乙缩醛和4-羟基-2E-壬烯酸（4-HNA）。
• ALLEVIATING OXIDATIVE STRESS DISORDERS WITH PUFA DERIVATIVES
  申请人：Shchepinov Mikhail S.

  公开号：US20110105609A1

  公开（公告）日：2011-05-05

  Some aspects of the invention provide for essential fatty acids which are substituted in specific positions to slow down oxidative damage by Reactive Oxygen Species (ROS), and to suppress the rate of consequent formation of reactive products, for the purpose of preventing or reducing the damage associated with oxidative stress associated diseases such as neurological diseases and age-related macular degeneration (AMD).

  本发明的某些方面提供了在特定位置被替代的必需脂肪酸，以减缓由反应性氧化物质（ROS）引起的氧化损伤，并抑制随之形成的反应性产物的速率，以预防或减少与氧化应激相关的疾病，如神经系统疾病和年龄相关性黄斑变性（AMD）相关的损伤。