(2E)-4-hydroxyoct-2-enal | 55-88-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-4-hydroxyoct-2-enal
• 英文别名: (E)-4-hydroxyoct-2-enal；4-hydroxynonenal；4-hydroxy-oct-2t-enal；4-Hydroxy-2-octenal
• CAS: 55-88-9
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: PYWFGGNTBVBZAT-GQCTYLIASA-N

物化性质

• 沸点：
  110-112 °C(Press: 2 Torr)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-羟基辛烯醛，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升高，KLOTHO mRNA和蛋白水平会降低（A7869）。

Uremic toxins such as 4-Hydroxyoctenal 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空间（胸腔积液）积聚的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：

  2,4-二硝基苯肼 、 (2E)-4-hydroxyoct-2-enal 生成 (E,1E)-1-[(2,4-dinitrophenyl)hydrazinylidene]oct-2-en-4-ol
  参考文献：
  名称：

  WERNER, A.;GRUNE, T.;SIEMS, W.;SCHNEIDER, W.;SHIMASAKI, H.;ESTERBAUER, H.+, CHROMATOGRAPHIA, 28,(1989) N-2, C. 65-68

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-1,1-dimethoxy-octane 在 氢氧化钾 作用下， 生成 (2E)-4-hydroxyoct-2-enal
  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

• 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。
• Raphanus with increased anthocyanin levels
  申请人：Koppert, Gerrit

  公开号：EP1290938A1

  公开（公告）日：2003-03-12

  The present invention relates to plants of the genus Raphanus containing increased levels of anthocyanins. In particular the edible sprouts and turnips of the Raphanus plants contain high levels of anthocyanins and thereby provide health-promoting effects. The anthocyanins in the Raphanus plants are present at a level of at least 100 nmol per gram of fresh weight and have an absorbance maximum at a wavelength in the range of 515 to 550 nm. The invention also provides methods for growing the Raphanus plants as purple sprouts, both in the form of alfalfa-type sprouts as well as in the form of two-leafed plantlets, referred to as cress or micro-vegetables. The invention further provides methods for producing anthocyanins based on growing the Raphanus plants and isolating anthocyanins therefrom.

  本发明涉及含有更多花青素的油菜属植物。特别是油菜属植物的可食用芽菜和萝卜含有大量花青素，因此具有促进健康的作用。油菜植物中的花青素含量至少为每克鲜重 100 nmol，在 515 至 550 nm 波长范围内具有最大吸光度。本发明还提供了种植紫花苜蓿植物的方法，这种紫花苜蓿植物既可以是紫花苜蓿类型的芽，也可以是两片叶子的小植株，即所谓的芹菜或微型蔬菜。本发明进一步提供了基于种植油菜植物并从中分离花青素的花青素生产方法。
• [EN] THERAPEUTICALLY ACTIVE MIXTURE OF GLUTATHION AND ANTHOCYAN COMPOUNDS
  申请人：OHLENSCHLÄGER, Gerhard

  公开号：WO1992003146A1

  公开（公告）日：1992-03-05

  (DE) Stoffgemisch zur therapeutischen Behandlung des menschlichen oder tierischen Körpers, das reduziertes Glutathion und mindestens eine Anthocyan-Verbindung der Gruppe Pelargonidin, Päonidin, Cyanidin, Melvidin, Petunidin, Delphinidin enthält, wobei das reduzierte Glutathion ganz oder teilweise durch mindestens ein Thiol-Derivat des Glutathions der Gruppe Methyl-Glutathionyl-(Thio)-Äther, Äthyl-Glutathionyl-(Thio)-Äther, Mono-Acetyl-Glutathionyl-(Thio)-Ester, Mono-Phosphorsäure-Glutathionyl-(Thio)-Ester ersetzt sein kann.(EN) A mixture of substances for therapeutically treating the human or animal body contains reduced glutathion and at least an anthocyan compound from the group composed of pelargonidine, peonidine, cyanidine, melvidine, petunidine and delphinidine. The reduced glutathion can be entirely or partially substituted by at least a thiol-derivate of glutathion from the group composed of methyl-glutathionyl-(thio)-ether, ethylglutathionyl-(thio)-ether, mono-acetyl-glutathionyl-(thio)-ester and mono-phosphoric acid glutationyl-(thio)-ester.(FR) Un mélange de substances servant au traitement thérapeutique du corps humain ou animal contient du glutathion réduit et au moins un composé d'anthocyane appartenant au groupe formé par la pélargonidine, la péonidine, la cyanidine, la melvidine, la pétunidine et la delphinidine. Le glutathion réduit peut être entièrement ou partiellement subsitué par au moins un dérivé thionique du glutathion appartenant au groupe formé par le méthyl-glutathionyl-(thio)-éther, l'éthyl-glutathionyl-(thio)-éther, le mono-acétyl-glutathionyl-(thio)-ester et le glutathionyl (thio)-ester d'acide mono-phosphorique.

  一种用于治疗人类或动物的物质混合物，含有减少的谷胱甘素和至少一种花青酸酸的类型，例如三甲基花青酸根多咯纺锤(Pelargonidine)、花青酸根多咯(Peonidine)、蓝花果糖्ल蓝藻酸(Cyanidine)、蓝藻酸(Melvidine)、紫罗兰藻酸(Petunidine)和金盏花藻酸(Delphinidine)，其中减少的谷胱甘素可以完全或部分地替换成至少一种带硫的谷胱甘素-衍生物，包括来自以下组的甲基-谷胱甘素-乙氧甲硫醇醚，乙基谷胱甘素-乙氧甲硫醇醚，甲基乙酰谷胱甘素-乙氧甲硫醇酯，甲基磷酸酸谷胱甘素-乙氧甲硫醇酯。
• (2E)-4-hydroxyalk-2-enals and 2-substituted furans as products of reactions of (2E)-4,4-dimethoxybut-2-enal with Grignard compounds
  作者：O. A. Garibyan、A. L. Ovanesyan、G. M. Makaryan、A. L. Petrosyan、Zh. A. Chobanyan

  DOI：10.1134/s1070428010030188

  日期：2010.3

  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.
• WERNER, A.;GRUNE, T.;SIEMS, W.;SCHNEIDER, W.;SHIMASAKI, H.;ESTERBAUER, H.+, CHROMATOGRAPHIA, 28,(1989) N-2, C. 65-68
  作者：WERNER, A.、GRUNE, T.、SIEMS, W.、SCHNEIDER, W.、SHIMASAKI, H.、ESTERBAUER, H.+

  DOI：——

  日期：——