(2E)-4-hydroxydec-2-enal | 18286-52-7

• 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: (2E)-4-hydroxydec-2-enal
• 英文别名: (E)-4-hydroxydec-2-enal；4-hydroxy-dec-2t-enal；4-Hydroxydecenal
• CAS: 18286-52-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: HDQZDHGXJUBNIK-SOFGYWHQSA-N

物化性质

• 沸点：
  133-135 °C(Press: 2 Torr)
• 密度：
  0.933±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-羟基癸烯醛，通过有机离子转运体（特别是OAT3）积极地转运到肾脏中。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氧化酶酶（特别是肾脏和心脏中丰富的NOX4）（A7868）来介导的。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已被识别为在抗衰老、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较高，KLOTHO mRNA和蛋白水平会降低（A7869）。

Uremic toxins such as 4-Hydroxydecenal 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

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

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，这种化合物可以导致尿毒症综合征。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、意识降低、激动、精神疾病、癫痫和昏迷。异常出血也可能发生，例如在非常轻微的损伤后自发或大量出血。心脏问题，如心律不齐、心脏周围囊炎症（心包炎）和心脏压力增加，也可能出现在尿毒症综合征患者中。由于肺部和胸壁之间的空间（胸腔积液）积聚液体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)

反应信息

• 作为反应物：
  描述：

  (2E)-4-hydroxydec-2-enal 以45%的产率得到2-正-己基呋喃
  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：

  (E)-癸-3-烯-1-醇 在 吡啶 、 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 28.17h， 生成 (2E)-4-hydroxydec-2-enal
  参考文献：
  名称：

  串联IBX促进伯醇氧化/中间β，γ-碳酸氢根醛向（E）-γ-羟基-α，β-烯醛的开放

  摘要：

  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。

  DOI：

  10.1002/asia.201900421

文献信息

• �ber die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 2. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, I
  作者：H. Esterbauer、W. Weger

  DOI：10.1007/bf01167149

  日期：——
• Iriye, Ryozo; Uno, Tsuyoshi; Ohwa, Ikuo, Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1841 - 1843
  作者：Iriye, Ryozo、Uno, Tsuyoshi、Ohwa, Ikuo、Konishi, Asako

  DOI：——

  日期：——
• Iriye; Konishi; Uno, Agricultural and biological chemistry, 1990, vol. 54, # 5, p. 1303 - 1305
  作者：Iriye、Konishi、Uno、Ohwa

  DOI：——

  日期：——
• �ber die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 3. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, II
  作者：H. Esterbauer、W. Weger

  DOI：10.1007/bf01167162

  日期：——
• Total syntheses of proposed (±)-trichodermatides B and C
  作者：Qian Li、Yan-Shuang Xu、Gregory A. Ellis、Timothy S. Bugni、Yu Tang、Richard P. Hsung

  DOI：10.1016/j.tetlet.2013.07.137

  日期：2013.10

  Total syntheses of putative (+/-)-trichodermatides B and C are described. These efficient syntheses feature the oxa-[3+3] annulation strategy, leading to B and C along with their respective C2-epimers. However, these synthetic samples are spectroscopically very different from the natural products. OFT calculations of C13 chemical shifts are conducted and the predicted values are in good agreement with those of synthetic samples, thereby questioning the accuracy of structural assignments of trichodermatides B and C. Published by Elsevier Ltd.